Authorship：Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

Molecular and charge arrangements in the solid state were controlled by a new building block: a triad molecule.

DOI： 10.1039/d3cc03198e

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

We have found that benzene-fused TTFs bearing polymerization sites could prolong the cycle life of LIBs via “in-cell polymerization”.

DOI： 10.1039/d3nj00289f

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Authorship：Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20220281

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20220191

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acsami.2c09302

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.inorgchem.1c04004

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.220064

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.210218

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20210115

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20200399

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20200406

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ejoc.202100039

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejoc.202100039

Publisher：Wiley  

DOI： 10.1002/ejoc.202100320

CiNii Research

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20200357

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.210070

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Peripherally arylated tetrathiafulvalenes with an anthraquinoid spacer (TTFAQs) have been synthesized by using palladium-catalyzed direct C-H arylation of the 1,3-dithiole rings. Electrochemical analysis by cyclic voltammetry has revealed that the new tetraarylated TTFAQs show one pair of simultaneous two-electron transfer waves as the parent TTFAQ does. The hydrolysis of the tetra( p -ethoxycarbonylphenyl)-substituted derivative affords the corresponding tetracarboxylic acid, which forms a new double-helical metal-organic framework upon complexation with cobalt(III) nitrate.

DOI： 10.1055/s-0040-1707177

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Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C-H arylation. In the presence of a catalytic amount of Pd(OAc)2, P(t-Bu3)·HBF4, and an excess of Cs2CO3, the C-H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations.

DOI： 10.3762/bjoc.16.86

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DOI： 10.1002/cssc.202000178

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cssc.202000178

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.tetlet.2020.151724

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.190703

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.190383

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

<p>Gold(<sc>iii</sc>) atoms reversibly deviate from the molecular plane on receiving thermal and photon energy.</p>

DOI： 10.1039/c9dt02377a

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ejoc.201801877

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ejoc.201900457

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/chem.201901030

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/chem.201805994

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/bcsj.20180157

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© 2018 American Chemical Society. Derivatives of a new bis-fused donor composed of TTF and extended TTF with an anthraquinoid spacer (TTFAQ) (2) were successfully synthesized. X-ray structure analysis of the tetrakis(methylthio) derivative 2Aa and its I3- salt revealed that the TTFAQ moieties of both 2Aa and 2Aa+ adopt the so-called saddle conformation similar to most neutral TTFAQs. The results obtained from the X-ray structure analysis and cyclic voltammetry suggest that a positive charge in 2Aa+ is unevenly distributed on the TTF moiety, while both positive charges of 22+ are mainly located on the TTFAQ moiety. In the first two-electron redox processes, an extra cathodic wave attributed to the coexistence of a different reduction process from the oxidation process was observed for most of the derivatives.

DOI： 10.1021/acs.orglett.8b01985

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.180371

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

X-ray structure analysis of the [5]radialene with quintuple 1,3-benzodithiol-2-ylidenes (4) and its tetracation salt, 4aCS(2) and (4a)(4+)(ReO4-)(4)(CH3CN), was successfully carried out. The neutral [5]radialene molecule in 4CS(2) adopted a non-planar structure with an envelope conformation of the central five-membered ring. In contrast, the central five-membered ring of 4a(4+) in (4a)(4+)(ReO4-)(4)(CH3CN) adopted a planar structure with significant contribution of an aromatic cyclopentadienide structure. An anion-pi interaction was observed between the ReO4- anion and the central five-membered ring in (4a)(4+)(ReO4-)(4)(CH3CN). The electronic structures of 4a and its oxidative species (4a(2+) and 4a(4+)) were estimated by density functional theory (DFT) calculations. The optimized structure of 4(2+) suggested the delocalization of a positive charges over two 1,3-benzodithiol-2-ylidene units through the central five-membered ring.

DOI： 10.1002/slct.201700288

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Molecular and crystal structures of dicationic tetrakis-(1,3-benzodithiol-2-ylidene)cyclopentanone (1b), (1b(2+))(2)-(ReO4-)(4)(CH3CN)(3)(H2O)0.7, were successfully determined by X-ray single-crystal diffraction. It was suggested that two 1,3-dithiol-2-ylidenes adjacent to the carbonyl group were effectively conjugated with each other. The remaining two 1,3-dithiol-2-ylidenes, where two positive charges were mainly distributed, were considerably twisted from the central five-membered ring.

DOI： 10.1246/bcsj.20160271

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Bis- and tris-fused pi-electron donors composed of extended tetrathiafulvalene with anthraquinoid spacers (4 and 5) were successfully synthesized. X-ray structure analysis of tetrakis(methylthio)-5 (5a) revealed that the molecule adopted a transoid-cisoid conformation. The cyclic voltammogram of 4a is composed of two pairs of two-electron redox waves, while the cyclic voltammogram of tetrakis(hexylthio) derivative 5b consists of one pair of four-electron redox waves and one pair of two electron redox waves, respectively. Spectroelectrochemistry of 4a and H-1 NMR spectrum of a 4b salt revealed that two positive charges in 4(2+) are distributed mainly on one TTFAQ (9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene) moiety.

DOI： 10.1021/acs.orglett.6b02944

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PHYSICAL SOC JAPAN  

The structural, transport, and magnetic properties of the new organic conductors (DMEDO-TTF)(2)X (X = ClO4 and BF4), where DMEDO-TTF is dimethyl(ethylenedioxy)tetrathiafulvalene, have been investigated. These compounds have a complete uniform stack structure, indicating that a quasi-one-dimensional 3/4-filled band without a dimerization gap is realized. The ClO4 and BF4 salts show a first-order metal-insulator (MI) transition at approximately 190 and 210 K, respectively, in the cooling process. The ground state is a nonmagnetic insulator on the basis of magnetic susceptibility measurements. Low-temperature X-ray diffraction measurements show that the MI transition originates in the anion ordering transition with a superstructure wave vector of q = (0, 1/2, 0) corresponding to the stacking direction; the uniform donor stacking structure changes to the tetramerized structure with a large shift of the donors. The shift of the anion toward the central two donors in a tetramer indicates that the insulating phase is a charge-density-wave state.

DOI： 10.7566/JPSJ.85.094701

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

Understanding the details of the electronic structure in face-to-face arranged tetrathiafulvalenes (TTFs) is very important for the design of supramolecular functional materials and superior conductive organic materials. This article is a comprehensive study of the interactions among columnar stacked TTFs using trimeric (trimer) and tetrameric (tetramer) TTFs linked by alkylenedithio groups (-S(CH2)(n)S-, n=1-4) as models of triple-and quadruple-decker TTF arrays. Single-crystal X-ray analyses of neutral trimeric TTFs revealed that the three TTF moieties are oriented in a zigzag arrangement. Cyclic voltammetry measurements (CV) reveal that the trimer and tetramer exhibited diverse reversible redox processes with multi-electron transfers, depending on the length of the -S(CH2)(n)S- units and substituents. The electronic spectra of the radical cations, prepared by electrochemical oxidation, showed charge resonance (CR) bands in the NIR/IR region (1630-1850 nm), attributed to a mixed valence (MV) state of the triple-and quadruple-decker TTF arrays. In the trimeric systems, the dicationic state (+2; 0.66 cation per TTF unit) was found to be a stable state, whereas the monocationic state (+1) was not observed in the electronic spectra. In the tetrameric system, substituent-dependent redox processes were observed. Moreover, pi-trimers and pi-tetramers, which show a significant Davydov blueshift in the spectra, are formed in the tricationic (trimer) and tetracationic (tetramer) state. In addition, these attractive interactions are strongly dependent on the length of the linkage unit.

DOI： 10.1002/chem.201601785

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER PHYSICAL SOC  

The results are presented for systematic heat capacity measurements of pi-d interacting systems of kappa-(BETS)(2)FeBr4 and kappa-(BETS)(2)FeCl4 [BETS = bis(ethylenedithio)tetraselenafulvalene] performed under in-plane magnetic fields. We observed sharp thermal anomalies at 2.47 K for kappa-(BETS)(2)FeBr4 and at 0.47 K for kappa-(BETS)(2)FeCl4 at 0 T that are associated with antiferromagnetic transitions of the 3d electrons in the anion layers. From analyses of the magnetic heat capacity data, we indicate that the two compounds show unconventional thermodynamic behaviors inherent in the pi-d interacting layered system. In the case of kappa-(BETS)(2)FeBr4, a small hump structure was observed in the magnetic heat capacity below the transition temperature when a magnetic field was applied parallel to the a axis. In the case of kappa-(BETS)(2)FeCl4, a similar hump structure was observed at 0 T that remained in the data with magnetic fields applied parallel to the a axis. We demonstrate that the temperature dependencies of the magnetic heat capacities scale well by normalizing the temperatures with dominant one-dimensional direct interactions (J(dd)/k(B)) of each compound. The field dependencies of the transition temperatures and the hump structures are elucidated in one simple magnetic field vs temperature (H-T) phase diagram. These results indicate that the thermodynamic features of both kappa-type BETS salts are essentially equivalent, and the observed hump structures are derived from the one-dimensional J(dd) interaction characters, which are still influential for magnetic features even in the long-range magnetic ordered states.

DOI： 10.1103/PhysRevB.93.245136

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Other Link： https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-15H03798/

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

In this study, we synthesized 2-(4-chloro-5-methyl-1,3-dithio1-2-ylidene)-5-(4,5-dimethy1-1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (ClMe3-TTP). Results show that the cation radical salts of ClMe3-TTP with PF6- and AsF6- anions show high conductivities (10(1) S cm(-1)) at room temperature and semiconducting behavior with low activation energy (24-27 meV). A crystal structure analysis of the PF6- and AsF6- salts reveals a 3:1 donor-anion ratio of these salts. The CIMe3-TTP molecules form one-dimensional columns along the a axis, and tape-structures, connected by the side-by-side S center dot center dot center dot S interactions, also form along the a axis. The calculated intracolumn and intratape overlap integrals are relatively large; however, the overlap integrals between the one-dimensional columns and the tapes are approximately 1/2-1/5 the value of the intracolumn and intratape overlap integrals. The band calculations suggest that they have one-dimensional electronic structures, indicating that they would comprise a Mott insulator.

DOI： 10.1246/bcsj.20140413

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Extensively conjugated tetrathiafulvalene (TTF) derivatives substituted with a TTF-fused 1,4-dithiafulven-6-yl group 4 have been synthesized. Theoretical calculation and X-ray crystal structure analysis of 4a demonstrated that the conformation A, in which the two TTF units are linearly oriented, is slightly more stable than the conformation B, which adopted orthogonal arrangement of two TTF units in the neutral state. Cyclic voltammetry revealed the presence of the intramolecular 1,5-S center dot center dot center dot S interaction that brings about the stabilization of the conformation B in the tricationic state.

DOI： 10.1246/cl.141182

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

The electron donor 2-isopropylidene-1,3-dithiolo[4,5-d]-4,5-ethylenediselenotetrathiafulvalene (3) provides two new molecular conductors, (3)(2)[M(CN)(2)] (M = Ag and Au). These salts crystallize in the triclinic P (1) over bar space group. The donor sheet structure of these salts is the so-called beta-type molecular array, in which the donor molecules form a head-to-tail dimer. The formation of considerable dimerization and the 2:1 donor-anion ratio result in an effectively half-filled electronic nature. These salts show metallic conducting behavior from room temperature. The metallic conducting behavior of (3) (2)[Ag(CN)(2)] was retained down to 8 K; however, the resistivity of (3)(2)[Au(CN)(2)] increased at around 50 K. The magnetic susceptibility of (3)(2)[Au(CN)(2)] suggests that the strength of the electron correlation for this salt is enhanced below 50 K.

DOI： 10.1002/ejic.201402006

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Dendritic tetrathiafulvalene (TTF) derivatives linked by methylenedithio groups 3 were synthesized. Cyclic voltamrnetry and spectroelectrochemistry analyses revealed the presence of considerable mutual interaction among multiple TTF units in the oxidation states.

DOI： 10.1246/cl.140092

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

A new cyclic tetrathiafulvalene (TTF) tetramer 1 was synthesized. The cyclic voltammogram of 1 consists of four pairs of two-electron redox waves. UV-vis-NIR spectra of the oxidative species of 1 suggest that 1(2+), 1(4+), and 1(6+) possibly adopt two pairs of dimeric TTF structures that interact with each other through the so-called side-by-side interaction.

DOI： 10.1246/cl.131231

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：MDPI AG  

The synthesis of new unsymmetrically benzene-fused bis (tetrathiafulvalene) has been carried out by a cross-coupling reaction of the respective 4,5-dialkyl-1,3-dithiole- 2-selenone 6-9 with 2-(4-(p-nitrophenyl)-1,3-dithiole-2-ylidene)-1,3,5,7-tetrathia-sindacene- 6-one 5 prepared by olefination of 4-(p-nitrophenyl)-1,3-dithiole-2-selenone 3 and 1,3,5,7-tetrathia-s-indacene-2,6-dione 4. The conversion of the nitro moiety 10a-d to amino 11a-d then dibenzylamine 12a-d groups respectively used reduction and alkylation methods. The electron donor ability of these new compounds has been measured by cyclic voltammetry (CV) technique. Charge transfer complexes with tetracyanoquino-dimethane (TCNQ) were prepared by chemical redox reactions. The complexes have been proven to give conducting materials. © 2014 by the authors
licensee MDPI, Basel, Switzerland.

DOI： 10.3390/ijms15034550

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PHYSICAL SOC JAPAN  

DOI： 10.7566/JPSJ.83.015002

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Spectroelectrochemistry of [5]radialenes with five 1,3-dithiol-2-ylidenes (DTs) (1) was carried out. The UV-vis-NER spectra of 1(2+) suggest delocalization of two positive charges over three DT units. X-ray structure analysis of an oxygen adduct (2)(2+)(AsF6-)(2)(PhCl)(1.5) reveals that 2(2+) has a cyclopentadienide structure in the central five-membered ring.

DOI： 10.1246/cl.130142

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER PHYSICAL SOC  

The quasi-one-dimensional (Q1D) molecular conductors (DIETSe)(2)MCl4 [M = Fe, Ga] undergo a spin density wave (SDW) transition below 12 K. The SDW ground state is suppressed by applying high pressure, recovering the Q1D Fermi surface which is confirmed by the appearance of Lebed resonance in the angle-dependent magnetoresistance (MR). Above the critical pressure of SDW, MR shows kink structures at high magnetic fields, reminiscent of field-induced spin density wave (FISDW) transition in both salts. The pi-d hybrid (DIETSe)(2)FeCl4 also exhibits an antiferromagnetic (AF) transition of d-electron spins at 2.5 K, below which the spin-flop-induced positive large MR are observed. The change in the interlayer MR reaches 130% at 10.5 kbar. The resistance anomalies associated with spin flop are also observed in the angle-dependent MR at low magnetic fields below 5 T, associated with clear hysteresis. A polar plot of these anomalies reveals the presence of hidden spin canting. Two magnetic easy axes of d-electron spins are found to be tilted +/- 16 degrees from the b axis towards the c axis. The interplay between the SDW instability of Q1D pi electrons and the local moments of AF d-electron spins is considered as the origin of the anomalous transport behaviors. DOI: 10.1103/PhysRevB.87.085117

DOI： 10.1103/PhysRevB.87.085117

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DOI： 10.1246/cl.130822

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DOI： 10.5517/ccznjz3

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Other Link： http://orcid.org/0000-0002-7119-2017

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER PHYSICAL SOC  

We report the molecular dipole effect on conduction electrons in the title superconductor. The angular-dependent magnetoresistance has a peak for fields nearly parallel to the conducting layer, and the peak width scales as the field component perpendicular to the layer, indicating incoherent interlayer transport. However, two closed Fermi surfaces are observed in quantum oscillation. Accordingly, crystallographically independent layers have different charge densities in a bulk single crystal. The electric dipole of tetrahydrofuran gives rise to interlayer charge disproportionation.

DOI： 10.1103/PhysRevLett.109.147005

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

We report the first observation of spin-flop-induced sharp positive magnetoresistance as large as 100% and nonvolatile magnetoresistive memory in a pi-d hybrid molecular conductor, (DIETSe)(2)FeCl4 [DIETSe = diiode-(ethylenedithio)tetraselenafulvalene]. The unprecedented magnetotransport phenomena originate from the coexistence of the spin density wave (SDW) of the quasi-one-dimensional (Q1D) pi electrons and the antiferromagnetic order of d-electron spins, indicating the interplay between the electronic instability of Q1D pi electrons and local moments of antiferromagnetic d-electron spins. These findings offer new possibilities in molecular electronics/spintronics.

DOI： 10.1021/ja308471u

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Bis-fused donors composed of (thio) pyran-4-ylidene-1,3-dithiole and tetraselenafulvalene (1a, 2a) and their bis(methylthio) derivatives (1b, 2b) were synthesized. Cyclic voltamograms of all the donors consisted of four pairs of one-electron redox waves, and it was suggested that a positive charge of 1(+center dot) and 2(+center dot) distributed mainly on the (thio) pyran-4-ylidene-1,3-dithiole moiety. X-ray structure analysis revealed that (1b)PF6(C6H5Cl)(0.5) and (2b)PF6(C6H5Cl) formed one-dimensional conducting stacks in which the donors were dimerized or tetramerized. In those salts, intramolecular charge disproportionation of the donors was suggested by X-ray structure analysis and density functional theory (DFT) calculation with UB3LYP/6-31G(d) basis function. A tight-binding band calculation suggested that these materials were band insulators. All the donors gave highly conducting TCNQ (7,7,8,8-tetracyanoquinodimethane) complexes and I-3(-) salts (sigma(rt) = 0.3-19 S cm(-1) on a compressed pellet) with very low activation energies of 0.017-0.040 eV, while single crystals of (1b)PF6(C6H5Cl)(0.5) and (2b) PF6(C6H5Cl) exhibited semiconductive behavior with large activation energies (E-a = 0.16-0.22 eV).

DOI： 10.3390/cryst2031092

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

A series of quasi-one-dimensional molecular conductors (DMEDO-TTF)(2)XF6 (X = P, As, and Sb), where DMEDO-TTF is dimethyl(ethylenedioxy)tetrathiafulvalene, undergo characteristic structural transitions in the range of 130-195 K for the PF6 salt and 222-242 K for the AsF6 salt. The dramatic structural transition is induced by the order of the ethylenedioxy moiety, and the resulting anion rotation leads to the reconstruction of the H center dot center dot center dot F interaction between the methyl groups and the anions. The unique hydrogen bonds play a crucial role in the transition. As a result, the molecular packing is rearranged entirely; the high-temperature molecular stacks with an ordinary quasi-triangular molecular network transforms to a quasi-square-like network, which has never been observed among organic conductors. Nonetheless, the low-temperature phase exhibits a good metallic conductivity as well, so the transition is a metal-metal (MM) transition. The resistivity measured along the perpendicular direction to the conducting ac-plane (rho(perpendicular to)) and the calculation of the Fermi surface demonstrate that the high-temperature metal phase is a one-dimensional metal, whereas the low-temperature metal phase has considerable interchain interaction. In the SbF6 salt, a similar structural transition takes place around 370 K, so that the quasi-square-like lattice is realized even at room temperature. Despite the largely different MM transition temperatures, all these salts undergo metal-insulator (MI) transitions approximately at the same temperature of 50 K. The low-temperature insulator phase is nonmagnetic, and the reflectance spectra suggest the presence of charge disproportionation with small charge difference (0.14).

DOI： 10.1021/ja303435n

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Tetrathiafulvalene derivatives condensed with 2-alkylidene-1,3-dithiole moiety, MeDTES (2-isopropylidene-1,3-dithiolo[4,5-d]-4,5-ethylenediselenotetrathiafulvalene), EtDTES (2-(pentan-3-ylidene)-1,3-dithiolo[4,5-d]-4,5-ethylenediselenotetrathiafulvalene), and CPDTES (2-cyclopentanylidene-1,3-dithiolo[4,5-d]-4,5-ethylenediselenotetrathiafulvalene) have been synthesized. Crystal structure analysis of MeDTES salts with Au(CN)(4)(-), ReO4-, and I-3 and a CPDTES salt with I-3 reveals that the donor-anion ratios of all salts are 1:1. Band calculation of (MeDTES)[Au(CN)(4)] suggests a quasi-one-dimensional Fermi surface that could be the result of the uniform stack of donor molecules. In spite of this stacking, the salt is a Mott insulator because of a large on-site Coulomb interaction U. (MeDTES)(ReO4)(H2O)(0.5) possesses Fermi points and exhibits semiconducting behavior with small activation energy (E-a = 0.058 eV). I-3(-) ions form disordered infinite chain in (MeDTES)(I-3)(DCE)(0.25), but those in (CPDTES)(I-3) exist as discrete ions. They show low conductivity (10(-4)-10(-2) S cm(-1)) at room temperature and the band calculation suggests that they are band insulator.

DOI： 10.3390/cryst2020393

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：IOP PUBLISHING LTD  

The temperature and polarization dependence of the optical reflectivity spectra of a quasi-one-dimensional 1/4-filled band system,. DMEDO-EBDT/2PF6, have been investigated. We observed clear anisotropy in the electronic structures corresponding to the anisotropic transport properties. The appearance of a charge gap (E-g &gt; 0.1 eV) and transfer of the spectral weight accompanied by the metal-insulator phase transition were clearly observed. In addition, a split of the intramolecular vibrational modes was observed, which strongly suggested the existence of charge disproportionation in the low temperature phase. We also observed a photoinduced reflectivity change, which implied the occurrence of a photoinduced phase transition from the low temperature insulating phase to the high temperature metallic phase.

DOI： 10.1088/0953-8984/24/19/195501

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

A new 2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (BDT-TTP) type donor, 2-(4,5-dimethoxy-1,3-dithiol-2-ylidene)-5-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (MOET-TTP) was synthesized and its magnetic and non-magnetic anion salts (MOET-TTP)2MCl4 (M=Fe and Ga), were prepared. These salts are isostructural and belong to the space group of P1. They show metal-like behavior down to 200K for the FeCl4 salt and 20K for the GaCl4 salt. The band structures of these salts are two-dimensional. The MCl4 anions are located between the donor columns and close to the ethylenedithio and methoxy groups of the donor molecules. The magnetic susceptibilities of the FeCl4 salts follow the CurieWeiss law with Curie constant of 4.3emuKmol-1 and Weiss temperature of =-1.8K, revealing a weak antiferromagnetic interaction of 3d spins of the FeCl4 anions. The Fe center dot Fe (6.508(3) angstrom) and Cl center dot Cl (3.784.69 angstrom) distances in the crystal structure of the salt are significantly long. Therefore, the direct magnetic interaction between the 3d spins of the nearest neighboring Fe3+ ions does not seem readily accessible.

DOI： 10.1002/pssb.201100674

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER PHYSICAL SOC  

We have systematically investigated the resistive superconducting transition in the layered organic superconductor kappa(H)-(DMEDO-TSeF)(2)[Au(CN)(4)](THF) [where DMEDO-TSeF is dimethyl(ethylenedioxy) tetraselenafulvalene and THF is tetrahydrofuran], which consists of two crystallographically independent conducting layers and one independent thick dielectric insulating layer. Applying a slight pressure of up to 0.35 GPa suppresses the superconducting phase. The angular dependence of the upper critical field and the short interlayer coherence length indicate that the present compound is a highly two-dimensional superconductor. The upper critical field parallel to the conducting layers exceeds the Pauli paramagnetic limit. These superconducting properties are consistent with the crystal structure in which the superconducting layers are well separated by a thick anion insulating layer.

DOI： 10.1103/PhysRevB.85.014504

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Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：WILEY-V C H VERLAG GMBH  

The title salt, where BSM-TTP is 2-[4,5-bis(methylseleno)-1,3-dithiol-2-ylidene]-5-(1,3-dithiol-2ylidene)-1,3,4,6-tetrathiapentalene, was prepared. The X-ray structure analysis reveals that the donors form teramerized columns, each of which is connected through an edge-to-edge chalcogen interaction. A tight-binding band calculation suggests that this salt is a semi-metal with small Fermi surfaces. Indeed, this salt exhibited high conductivity of sigma(rt) = 25 S cm(-1) at room temperature, and showed metallic conducting behaviour down to T-MI = 170 K. (C) 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

DOI： 10.1002/pssc.201100690

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Several derivatives of a new donor-acceptor diad 1 composed of DT-TTF and dicyanomethylidene group were synthesized. The IR spectra of 1 demonstrated considerable contribution of a polarized structure. Electronic spectra and molecular orbital calculation suggested that the absorption maximum of 1 was due to NHOMO-LUMO transition. Cyclic voltammetry revealed that the compound 1 exhibited three-stage of oxidation and one-stage of reduction processes. The bis(methylthio)-substitudted derivative 1a exhibited conductivity of 10(-6) S cm(-1) in spite of a single-component material.

DOI： 10.3987/COM-11-12277

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Trimeric and tetrameric TTFs 1 and 2 linked alternately by methylenedithio groups were synthesized. Cyclic voltammetry and spectroelectrochemistry indicated that the dicationic state of tetrameric TTF 2 exhibited the mixed-valence state constructed not by the tetrameric TTF units but by two dimeric mutually independent TTF units.

DOI： 10.1246/cl.2011.883

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

New dimeric and trimeric TTF derivatives with methylenedithio spacers (1ab, 2a, and 2b) have been synthesized. X-ray structure analysis revealed that TTF units of the dimer 1b adopted distorted face-to-face overlapping arrangement both in intra- and intermolecular stacking. Cyclic voltammetric study indicated that trimeric 2a was in favor of taking di- and tetracationic states, while the dimeric la was in favor of taking a monocation. The absorption spectroscopic study suggested an existence of the strong face-to-face interaction particularly in di-, tri-, and tetracationic state of the trimeric TTF derivatives.

DOI： 10.1021/ol201025g

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Novel 1,3-dithiole[4]dendralene derivatives 3 with two thiophene spacers were synthesized. Cyclic voltammetry and spectroelectrochemistry suggested the dications of most derivatives of 3 have dimeric thiophene quinoid radical cation structures, while tetramethyltetrakis(methoxycarbonyl) derivative 3Bd adopts a vinylogous TTF dication structure.

DOI： 10.1246/cl.2011.467

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PHYSICAL SOC JAPAN  

The anisotropy of superconducting coherence lengths of the layered organic superconductor kappa(L)-(DMEDO-TSeF)(2)[Au(CN)(4)](THF) with domain structures has been investigated, where DMEDO-TSeF is dimethyl(ethylenedioxy) tetraselenafulvalene and THF is tetrahydrofuran. The field angle dependence of the upper critical field and the short interlayer coherence length indicate that the present compound is a two-dimensional superconductor. Although this compound has domain walls parallel to the conducting layer depending on the orientation of the THF molecules, the interlayer coherence length shorter than the structural correlation length shows that the domain walls parallel to the conducting layers do not affect the superconductivity.

DOI： 10.1143/JPSJ.80.054706

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Several molecular conductors based on CP-TTP, where CP-TTP is 2-(4,5-cyclopenteno-1,3-dithiol-2-ylidene)-5-(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene, have been prepared. X-ray structure analyses revealed that all the CP-TTP conductors obtained so far have beta-type array of the donors regardless of the counter anions. Among them, the ReO4- and Au(CN)(2)(-) salts exhibited metallic conducting behavior down to 10K.

DOI： 10.1246/cl.2011.452

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER PHYSICAL SOC  

The Fermi surface of the layered organic superconductor kappa(L)-(DMEDO-TSeF)(2)[Au(CN)(4)](THF) has been investigated, where DMEDO-TSeF is dimethyl (ethylenedioxy) tetraselenafulvalene. Band-structure calculations show that the fundamental Fermi surface is not circular, but elliptical with an eccentricity of 0.76, leading to a large orbital overlap in the extended Brillouin zone. This symmetry is lowered by a structural phase transition at 209 K at which domains form. The magnetic breakdown orbit is observed in the Shubnikov-de Haas oscillations under the low-field region, consistent with the small energy gap at the zone boundary. The observation of the Shubnikov-de Haas effect shows that the present compound has a clean electronic system despite the domain structures.

DOI： 10.1103/PhysRevB.83.012505

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

A new tetrathiapentalene (TTP) donor 2-(4,5-dimethoxy-1,3-dithiol-2-ylidene)-5-(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (DMO-TTP) has been synthesized, and the PF6 and AsF6 salts have also been prepared by electrochemical crystallization. X-ray structure analyses have revealed that intermolecular and intramolecular CH center dot center dot center dot O hydrogen bondings are constructed in the neutral crystal and the cation radical salts, respectively. The PF6 and AsF6 salts have a so-called A-type arrangement of the donors and show metallic behavior down to around 10 K.

DOI： 10.1246/cl.2011.81

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Language：Japanese   Publisher：The Society of Physical Organic Chemistry, Japan  

Tetrathiafulvalene (TTF) and its derivatives are known as donor components of molecular conductors. The strong face-to-face interaction between TTF molecules plays significant role in high conductive molecular conductors. In our previous works, we have synthesized dimeric, trimeric and tetrameric TTF with metylendithio spacers and studied their electrochemical properties. Herein, we report synthesis of pentameric, hexameric, heptameric and octameric TTF with methylendithio spacers together with their electrochemical propaties.

DOI： 10.11494/kisoyuki.2011.0.343.0

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

A new donor (ST-STP), in which tetrathiafulvalene and tetraselenafulvalene are fused, has been synthesized. This donor shows unexpectedly large on-site Coulomb repulsion compared with other bis-fused TTF systems In (ST-STP)ReO4, intramolecular charge disproportionation is suggested by the crystal structure and transport properties.

DOI： 10.1246/cl.2010.1093

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE BV  

We synthesized vinylogous 4 5-ethylenedioxy-tetrathiafulvalenes (EDO-TTFs) 4 5-ethylenedioxy-2 2&apos;-ethanediylidenebis(1 3-dithiole) (EDO-EBDT) 4 5-dimethyl-4&apos; 5&apos;-ethylenedioxy-2 2&apos;-ethanediylidenebis(1 3-dithiole) (DMEDO-EBDT) 4 5-bis(thiomethyl)-4&apos; 5&apos;-ethylenedioxy-2 2&apos;-ethanediylidenebis (1 3-dithiole) (BTMEDO-EBDT). and 4 5-bis(methoxycarbonyl)-4&apos; 5&apos;-ethylenedioxy-2 2&apos;-ethanediylidenebis(1,3-dithiole) (BMCEDO-EBDT) The cyclic voltammograms of the vinylogous EDO-TTFs show two pairs of single-electron redox waves The first oxidation potentials (E(1)) of vinylogous EDO-TTFs are lower than those of the related TTFs, indicating that the electron donating abilities of new donors are stronger than those of the corresponding TTFs The smaller E(2)-E(1) values of new donors compared with those of the related TTFs suggest a decrease in the on-site Coulombic repulsion in the dication state X-ray crystal structure analysis of BMCEDO-EBDT reveals that the inter-molecular C-H O type hydrogen bond is constructed between the hydrogen atom and the oxygen atom of the ethylenedioxy group Single crystalline TCNQ complexes of DMEDO-EBDT and BTMEDO-EBDT have been prepared and their conducting properties and crystal structure have been investigated The TCNQ complexes of DMEDO-EBDT and BTMEDO-EBDT show low electrical conductivities (art sigma(pi) &lt; 10(-6)S cm for (DMEDO-EBDT)(TCNQ)(chlorobenzene) and sigma(pi)=2 2 X 10(-3)S cm(-1) for (BTMEDO-EBDT)(TCNQ)) clue to DDAA-type alternate stacking (C) 2009 Elsevier B V All rights reserved

DOI： 10.1016/j.physb.2009.12.024

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：JAPAN SOC APPLIED PHYSICS  

Following the previous preparation of the cyclopentane-capped tetrathiapentalene (TTP) molecule (1), we have prepared new TTP-based organic semiconductors capped with cyclobutane (2) and cyclohexane (3) units, and investigated their crystal and thin-film structures together with the field-effect transistor (FET) characteristics. The molecule capped with cyclobutane units (2) forms a uniform stacking structure extending in different directions, leading to a three-dimensional intermolecular interaction. In the crystal of the cyclohexane- capped compound (3), the S-shaped molecules stack uniformly along the crystallographic b- and c-axes, and the estimated intermolecular interaction is two dimensional. The organic FETs (OFETs) prepared by vapor deposition show markedly different mobilities, 1.3 x 10(-2) and 0.1 cm(2) V-1 s(-1) for 2 and 3, respectively, although the electrochemical properties are almost the same. The striking difference between the FET properties is attributed to the very different crystal structures of the TTP molecules depending on the terminal groups. (C) 2010 The Japan Society of Applied Physics

DOI： 10.1143/JJAP.49.01AB10

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DOI： 10.1016/j.nima.2010.03.085

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：JAPAN SOCIETY APPLIED PHYSICS  

A small dithienothiophene core compound 2,6-dihexanoyldithieno[3,2-b;2&apos;,3&apos;-d]thiophene was synthesized and its electric properties were evaluated. The carrier mobility in the mesophase was measured by time-of-flight transient photocurrent technique. The mobility reached around 0.1 cm(2) V(-1) s(-1) for holes and 0.05 cm(2) V(-1) s(-1) for electrons, which is the highest level measured in the mesophases by time-of-flight method. The field effect mobility was evaluated for vapor-deposited thin films on an amorphous fluoropolymer insulator. Only p-type operation was observed and the hole mobility dropped to 1.5 x 10(-3) cm(2) V(-1) s(-1) due to poor injection from the source/drain electrodes. (C) 2009 The Japan Society of Applied Physics

DOI： 10.1143/APEX.2.041502

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Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：IOP PUBLISHING LTD  

Se-77 NMR signals were observed in the metallic and insulating states of the quasi-one-dimensional organic compound (DIETSe)(2)GaCl4. The Se-77 NMR spectra at low temperatures are broadened, indicating the presence of magnetic ordering. The shape of the spectra in the magnetically ordered state is characteristic of the spin density wave (SDW) ordering. The divergent behavior of the temperature dependence of the nuclear spin-lattice relaxation rate suggests that the SDW ordering occurs at about 7 K which is lower than the metal-insulator transition temperature of 12 K.

DOI： 10.1088/1742-6596/150/4/042124

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

Bromo-tetracyanoazulenequinodimethanes have been synthesized by the one-pot reaction of 1,3,5-tribromoazulene with tetracyanoethylene oxide. These electron acceptors formed corresponding charge transfer complexes with tetrathiotetracene, some of which were shown to have conducting ability.

DOI： 10.1080/17415990902930390

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Hexamethylenetetrathiafulvalene (HMTTF) derivatives substituted by tert-butyl, n-pentyl, and 1,1-dimethylpropyl groups are prepared, and the transistor properties are investigated. The compounds substituted by bulky tertiary groups exhibit high mobilities up to 0.98 cm(2)/Vs in the thin-film transistors and 2.3 cm(2)/Vs in the single-crystal transistors. At the same time these compounds realize low threshold voltages close to zero and large on-off ratios. The high mobility and the low threshold voltage are maintained more than one month in air. The single-crystal X-ray structure analyses reveal uniform stacking structures. These observations demonstrate that the low threshold voltage and the stable device performance are not solely determined by the energy levels, but are remarkably improved by the closely packed structures derived from the bulky alkyl groups.

DOI： 10.1039/b907592e

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

A study was conducted to analyze a new skeleton of organic field-effect transistors (OFET) materials, tetrathiapentalene (TTP), the compounds of which have considerably higher oxidation potentials than tetrathiafulvalene (TTF), which is expected to be advantageous to device stability. Compounds 1 and 2 were synthesized by phosphite-mediated coupling reactions of the starting material, 3 and 4, which were prepared by the Wittig reaction between a TTP-based phosphonate and the ketone. The alkyl-capped TTP molecules were obtained by a phosphite-mediated contracting-coupling reaction, in which two TTP units merged into one. Compound 2 is a high-performance OFET material, the relatively high oxidation potential of which is responsible for both stability and small threshold voltage. It is also notable that introduction of the outer ring system entirely changes the crystal and thin-film structures, and this is important in achieving the desired OFET properties.

DOI： 10.1021/cm801404d

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER PHYSICAL SOC  

Structural properties of the layered organic superconductor kappa(L)-(DMEDO-TSeF)(2)[Au(CN)(4)](THF) have been investigated, where DMEDO-TSeF is dimethyl(ethylenedithio)tetraselenafulvalene. We have found that a structural phase transition occurs at T(d)=209 K, and that only the (0 0 l) Bragg reflections split into two along the b(*) direction below T(d). The low-temperature structure is composed of two monoclinic domains with the space group P2(1)/n11. The low-temperature monoclinic phase has two crystallographically independent dimers in a conducting layer, suggesting that the present compound potentially borders on the checkerboard-type charge ordered state, and has possibly different symmetry of superconductivity from the ordinary kappa-type superconductors.

DOI： 10.1103/PhysRevB.76.134517

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

Five diiodo (ethylene dichalcogeno) tetrachalcogenofulvalenes, DIEDSS (2-(5,6-dihydro[1,3]diselenolo[4,5-b][1,4]diselenin-2-ylidene)-4,5-diiodo-1,3-dithiole), DIET-STF -2-(4,5-diiodo-1,3diselenol-2-ylidene)-5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithi- inel, DIEDS-STF (2-(4,5-diiodo-1,3-diselenol-2-ylidene)-5,6dihydro[1,4]diselenino[2,3-d](1,3-1-dithiole), DIEDS-STF {2-(4,5diiodo-1,3-diselenol-2-ylidene)-5,6-dihydro[1,3]diselenolo[4,5- b][1,4]dithime}, and DIEDSSe (2-(4,5-diiodo-1,3-diselenol2-ylidene)-5,6-dihydro[1,3]diselenolo[4,5-b][1,4]diselenine), have been synthesized without the use of the highly toxic reagent CSe2, and their Au(CN)(4) salts have been prepared by electrochemical oxidation. Characteristic I center dot center dot center dot N iodine bonds are constructed in all crystals, and their packing motifs are classified into two groups by the difference in the space group symmetry. The salt of DIEDSS crystallizes in the monoclinic C2/c space group and a novel helical supramolecular architecture is constructed by the strong and directional I center dot center dot center dot N iodine bond. On the other hand, the rest of the four salts crystallize in the triclinic P (1) over bar space group and their donor packing motifs belong to the so-called beta-type. Conducting properties of the -type salts strongly depend on the number and positions of the selenium atoms on the donor molecule. The salts based on the diselenadithiafulvalene (DSDTF) derivatives, DIET-STF and DIEDS-STF, show metal-semiconductor transition and the salt of fully selenated pi-donor DIEDSSe shows stable metallic behavior down to 1.6 K. On the other hand, (DIETSe)(2)[Au(CN)4] is semimetallic down to low temperature and the superconducting transition occurs at around 2 K (onset).
((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451, Weinheim, Germany, 2007)

DOI： 10.1002/ejic.200700530

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE BV  

We have found that the initial permeability mu' of Co(2)Z ferrite is improved by the substitution of Ti4+ and Zn2+ ions for Fe3+ ions. The substituted sample of Ba3Co2TixZnxFe24-2xO41 with x = 0.85 has a maximum mu' of 24, which is twice as large as that of the non-substituted sample with x = 0. The particle size and shape are changed by the substitution. This is influential in the densification and the preferential orientation of a toroidal-shape sample, which results in the improvement of mu'. (C) 2006 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.jmmm.2006.10.004

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

The unsymmetrical pi donor dimethyl(ethylenedioxy)tetraselenafulvalene (DMEDO-TSeF) has provided six new organic superconductors with a monovalent square-planar [Au(CN)(4)](-)ion and cyclic ethers as solvent of crystallization. The six new organic superconductors kappa-(DMEDO-TSeF)(2)Au(CN)(4)](solv.) [solv.=1,3-dioxolane (DOL), 2,5-dihydrofuran (DHF), tetrahydropyran (THP), 1,3-dioxane (1,3-DOX), 3,4-dihydro-2H-pyran (DHP), or 1,4-dioxane (1,4-DOX)] are classified into two subphases kappa(L) and kappa' according to the differences in their space group symmetry. kappa(L)- (DMEDO-TSeF)(2)[Au(CN)(4)](solv.) (solv.=DOL, DHF, THP, 1,3-DOX or DHP) crystallizes in the orthorhombic space group Pnma, and T-c of the kappa(L) phase varies by 1.7-5.3 K according to the size and shape of the solvent of crystallization. On the other hand, kappa'(DMEDO-TSeF)(2)[Au(CN)(4)](solv.) (solv.=DOL or 1,4-DOX) crystallizes in the noncentrosymmetric monoclinic space group Cc. The kappa'-phase containing 1,4-DOX shows superconductivity at 4.2 K, but the kappa'-phase containing DOL does not show superconductivity down to 1.4 K. Systematic investigation of the six new organic superconductors, together with the two previously reported superconductors kappa(H)- and kappa(L)- (DMEDO-TSeF)(2)[Au(CN)(4)](THF), revealed that the T-c of the present system is finely tunable by utilizing the effect of the solvent of crystallization.

DOI： 10.1002/chem.200700314

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DOI： 10.1016/j.nima.2007.06.098

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The preparation, crystal structures, extended Huckel theory band structure, and density functional theory (DFT) calculations and conducting and magnetic properties of seven new charge-transfer salts, formulated as (D)(2)[M-III(isoq)(2)(NCS)(4)], where D = DIET (diiodo(ethylenedithio)tetrathiafulvalene), DIETS (diiodo(ethylenedithio)diselenadithiafulvalene), M = Cr, Ga, and isoq = isoquinoline, are reported. For each donor two different phases called a and b were obtained. Crystal data for (DIET)2[Cr(isoq)2(NCS)41 (1) are as follows: phase a, triclinic P1, a = 9.8645(6) (A) over circle, b = 10.3255(8) (A) over circle, c = 13.7712(8) (A) over circle, alpha = 87.905(5)degrees, beta = 75.981(5)degrees, gamma = 80.712(2)degrees; phase b, triclinic P1, a = 10.6760(5) (A) over circle, b = 11.3000(6) (A) over circle, c = 11.3930(9) (A) over circle, alpha = 101.256(2)degrees, beta = 96.755(2)degrees, gamma = 97.342(5)degrees. All compounds exhibit semiconductive behavior with room-temperature resistivity ranging from 2 x 10(3) to 5 x 10(4) Omega cm. Donors in the mixed-valence-state form dimers. They are connected to anions through very short I center dot center dot center dot S contacts (S2 center dot center dot center dot I2 = 3.248(2) (A) over circle for 1a). The magnetic measurements and spin density DFT calculations revealed that iodine atoms are good structural agents but are poor magnetic mediators to promote superexchange interactions between the donors and the inorganic anions. Our analyses reveal also that in these charge-transfer salts the magnetic interactions between spin carriers are mainly ensured by short intermolecular S center dot center dot center dot S contacts.

DOI： 10.1021/cm052199q

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Novel organic conductors based on four diiodotetrathiafulvalene derivatives, DIET (2-(4,5-diiodo-[1,3]dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiine), DIETSe (2-(4,5-diiodo-[1,3]diselenol-2-ylidene)-5,6-dihydro-[1,3]diselenolo[4,5-b][1,4]dithiine), DIEDO (2-(4,5-diiodo-[1,3]dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxine) and DIEDOSTF (2-(4,5-diiodo-[1,3]diselenol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxine) have been prepared using spherical halide ion X- (X = Cl, Br) as the counter anion. Crystal structure analyses have revealed that all halide salts contain supramolecular structures tailored by the strong I. X iodine bond and their molecular arrangement depends on the combination of the group 16 elements included in the donor molecule. The temperature dependence of the electrical resistivity of (DIET)(2)X(H2O)(2) is metallic down to 4.2 K, and they have ideally two-dimensional Fermi surfaces within the donor layer. (DIETSe)(2)X(CH2Cl2) salts show small temperature dependence of the resistivity down to low temperatures and their "double column'' structure is dominated by the Y-shaped architecture composed of the halide ion and the crystalline solvent. On the other hand, (DIEDO)(2)X and (DIEDO-STF)(2)X are semiconducting from room temperature. They have another type of "double column'' structure, i.e. the adjacent donor molecules along the side-by-side direction are solid-crossing and two types of column are included in the donor layer. The packing motifs of the halide salts based on the oxygen-substituted donor molecules are the same but their electronic states are sensitive to changes in the chalcogen atoms on the inner TTF skeleton.

DOI： 10.1039/b512036e

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

We have developed two novel organic superconductors kappa(H)- and kappa(L)-(DMEDO-TSeF)(2)[Au(CN)(4)](THF) (DMEDO-TSeF = dimethyl(ethylenedioxy)tetraselenafulvalene) with the onset transition temperatures of 4.8 K for the kH- phase and 3.0 K for the kL- phase at ambient pressure, where DMEDO-TSeF is the second example following tetramethyltetraselenafulvalene (TMTSF) after an interval of 25 years as a sulfur-free donor providing a bulk organic superconductor.

DOI： 10.1039/b516940b

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

The low temperature transport properties of the pi-d system (DIETSe)(2)MCl4 [ M Fe, Ga] are investigated under the high magnetic fields and high pressures. Anomalous behaviors in the magnetic field dependence of resistance are observed in the magnetic Fe salt below about 2K, while such anomalous behaviors are absent in the nonmagnetic Ga salt, suggesting the strong interaction between the itinerant pi-electrons and the localized moments of d-electrons in (DIETSe)(2)FeCl4.

DOI： 10.1080/15421400600698238

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Conducting cation radical salts based on a pyrazine-fused iodine-bonded pi-donor diiodo( pyrazino) tetraselenafulvalene (DIPSe) and octahedral anions AF(6) ( A = P, As, Sb) have been prepared by electrochemical oxidation. X-Ray structure analysis revealed that these three salts are isostructural and crystallize in the hexagonal P6(3)/mcm space group. There is a strong and directional I center dot center dot center dot N iodine bond among the donor molecules, which is 18 - 19% shorter than the sum of the van der Waals radii. The hexagonal lattice is filled with the equilateral triangles of the donor molecules tailored by the I center dot center dot center dot N iodine bond and there are also two types of supramolecular channels including the counter anion and the crystalline solvent. The room temperature resistivities of these three salts are in the order of 10(-2) Omega cm with metallic behaviour and they show a gentle upturn at around 250 K. In addition to the high-symmetrical crystal structure and the metallic conductivity, high yield recovery of the neutral pi-donor from the cation radical salts has been accomplished by a simple chemical reaction. In situ H-1-NMR monitoring of the reaction process indicates that the DIPSe cation radical was reduced by water and the characteristic supramolecular channels, which allow water molecules to access the cation radicals deep in the crystal, are essential for smooth progress of the recovery process.

DOI： 10.1039/b611010j

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Eight cation radical salts based on halogenated tetraselenafulvalene (TSeF) derivatives, dibromo( ethylenedithio) tetraselenafulvalene (DBrETSe) and diiodo( ethylenedithio) tetraselenafulvalene (DIETSe), were prepared using magnetic and nonmagnetic MX4 counter anions ( M = Fe, Ga; X = Cl, Br). Crystal structures of the DBrETSe salts depend on the halogen species on the MX4 counter anion. The MCl4 salts of DBrETSe are isostructural and crystallize in the orthorhombic space group Ibam and those of the MBr4 salts crystallize in the monoclinic space group C2/c. On the other hand, all four MX4 salts of DIETSe are isostructural and crystallize in the orthorhombic space group Ibam. In all eight crystals, donor molecules form a so-called beta-type molecular arrangement and characteristic halogen bonds between the halogen atoms on the edge of the donor molecules and those of the counter anions are observed. (DBrETSe)(2)MX4 (M = Fe, Ga; X = Cl, Br) show stable metallic behaviour down to 4.2 K. This is in contrast to their iodinated analogues (DIETSe)(2)MCl4 (M = Fe, Ga), which show a metal - semiconductor transition at 11 K for the FeCl4 salt and at 12 K for the GaCl4 salt. No metal - semiconductor transition is observed for (DIETSe)(2)GaBr4, which contains the nonmagnetic anion, but the transition is observed at 7.2 K for the corresponding FeBr4 salt, which contains a magnetic anion, indicating that the metal - semiconductor transition of ( DIETSe)(2)FeBr4 correlates to the pi - d electronic interaction through the I center dot center dot center dot Br halogen bonds. Antiferromagnetic orderings of d spins of the FeX4 anions are observed in (DBrETSe)(2)FeX4 and (DIETSe)(2)FeX4 (X = Cl, Br). In contrast to the low Neel temperature (T-N approximate to 2.5 K) of the FeCl4 salts, the antiferromagnetic orderings occur at relatively high temperatures, i.e. T-N = 7.5 K for (DBrETSe)(2)FeBr4 and T-N = 7.0 K for (DIETSe)(2)FeBr4. Since the metallic state of (DBrETSe)(2)FeBr4 remains below T-N, this salt is classified as a novel antiferromagnetic organic metal. On the other hand, the antiferromagnetic ordering of the d spins in (DIETSe)(2)FeBr4 takes place cooperatively with the metal - semiconductor transition around 7 K. These antiferromagnetic orderings of the d spins between the FeX4 anions cannot be explained by direct anion - anion interactions because of their long halogen. halogen distances between the FeX4 anions, and the importance of the pi - d interaction between the donors and the counter anions through the halogen bonds is strongly suggested.

DOI： 10.1039/b605420j

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

Synthesis, crystal structure and physical properties of k-(BEDO-TSeF) I-2(3), (1) are reported. 1 is the first example of a cation radical salt based on BEDO-TSeF, which is the latest chalcogen analogue of BEDT-TTF.

DOI： 10.1080/15421400600697883

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

DOI： 10.1080/10426500590913249

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A novel unsymmetrical tetraselenafulvalene (TSeF)-type donor dimethyl( ethylenedioxy) tetraselenafulvalene (DMEDO-TSeF) has been synthesized without the use of the highly toxic reagent CSe2 and the structures and properties of its cation radical salts with octahedral anions are described.

DOI： 10.1039/b511820d

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ACADEMIC PRESS INC ELSEVIER SCIENCE  

A novel conjugation-elongated bis(ethylenedithio)tetraselenafulvalene (BETS) type donor, 2,5-bis(4,5-ethylenedithio-1,3-diselenol-2-ylidene)-2,3,4,5-tetrahydrothiophene (BEDT-HBDST) and its magnetic and non-magnetic anion salts, (BEDT-HBDST)(2)MX4 (MX4- = FeCl4-, GaCl4-, FeBr4- and GaBr4-), were prepared. These four salts are isostructural and belong to the space group of P2/c. They showed semiconducting behavior with small activation energies (59-64 meV). The band structures of these salts are quasi one-dimensional and there is a midgap between the upper band and the lower band, since the degree of dimerization is significant in the stacking direction. The MX4- ions are located between the donor columns and near to the ethylenedithio moieties of the donor molecules. The magnetic susceptibilities of the FeCl4- and FeBr4- salts follow the Curie-Weiss law with Curie constants of 4.6 and 4.8 emu K mol(-1) (sum of the spins of S = 5/2 and S = 1/2) and negative Weiss temperatures of theta = -1.2 and -4.9 K, respectively, revealing a weak antiferromagnetic interaction of 3d spins of the FeCl4- and FeBr4- anions. The (FeFe)-Fe-... (6.66-7.60 Angstrom), (ClCl)-Cl-... (4.81-4.82 Angstrom) and (BrBr)-Br-... (4.74-4.77 Angstrom) distances in the crystal structures of these salts are significantly long. Therefore, the direct magnetic interaction between the 3d spins of the nearest neighboring Fe3+ ions appears to be not readily accessible. (C) 2003 Elsevier Inc. All rights reserved.

DOI： 10.1016/j.jssc.2003.08.030

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DOI： 10.1143/JPSJ.73.254

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Bis(ethylenedioxy)tetraselenafulvalene (BEDO-TSeF) has been synthesized using elemental selenium as the only source of the selenium atoms, and its crystal structure and electrochemical properties are examined and compared with its sulfur analogues.

DOI： 10.1039/b403559c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Novel selenium analogues of diiodo(ethylenedithio)-diselenadithiafulvalene (DIETS) have been successfully derived from 1,3-diselenole-2-thione, which could be synthesized without the use of the highly toxic reagent CSe2.

DOI： 10.1039/b406092j

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE SA  

The iodine-based intermolecular interaction, i.e. iodine bond is highly useful for structure control of organic conductors and a wide variety of supramolecular conductors including a superconductor have been developed. In this paper, we focus our attention on exotic iodinated donor molecules DIETS (diiodo(ethylenedithio)diselenadithiafulvalene) and DIETSe (diiodo(ethylenedithio)tetraselenafulvalene). Syntheses, structure and electronic properties of a supramolecular superconductor and a new series of organic metals are reported together with an outline of the iodine bonding architecture.

DOI： 10.1016/S0379-6779(02)00786-5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE SA  

We present the low-temperature crystal structures of (BDTFP)(2)PF6 and (BDTFP)(2)AsF6 below the phase transition temperatures (T-p). In the former compound, the c-axis is doubled and thus the dimerized structure changed into a tetramerized structure. At the same time, a new charge-transfer (CT) transition appears at 7000-8000 cm(-1). These two findings are consistent with the non-magnetic state below T-p. In the latter, on the other hand, the dimerized structure is maintained below T-p, and instead AsF6 ion rotates along with the ca. 10degrees rotation of BDTFP. This structural change is the origin of the first-order phase transition to a paramagnetic state. (C) 2002 Elsevier Science B.V. All rights reserved.

DOI： 10.1016/S0379-6779(02)00298-9

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE SA  

We have synthesized novel selenium-containing pi-extended donors, BEDT-HBDST and BEDT-HSTT. The PF6, AsF6 and SbF6 salts of BEDT-HBDST showed broad rho(max) at around 120, 95 and 85 K, respectively, and metallic behavior down to 2 K. The quasi-one-dimensional metallic band structures are calculated for the PF6 and AsF6 salts of BEDT-HSTT with an alpha'-type donor arrangement, although these salts showed semiconducting behavior. (C) 2002 Elsevier Science B.V. All rights reserved.

DOI： 10.1016/S0379-6779(02)00377-6

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DOI： 10.1007/s00259-003-1301-3

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

We developed a new CSe2-free protocol for the synthesis of [1,3]diselenole-2-thione and converted it to tetraselenafulvalene derivatives without any selenium-sulfur exchange side reactions.

DOI： 10.1039/b304136k

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

N,N'-Dicyano-p-acepleiadylenequinonediimine (DCNAPQ-DI) and its 1,2-dibromo derivative (Br-2-DCNAPQ-DI), a new family of acepleiadylene-based DCNQI type electron acceptors have been synthesized. Br-2-DCNAPQDI exhibiting the first half-wave reduction potential of -0.03 V vs SCE afforded a fairly high conducting Cu salt.

DOI： 10.1246/cl.2002.1004

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PHYSICAL SOC JAPAN  

ESR and H-1-NMR investigations of the quasi-one-dimensional organic conductors, (BDTFP)(2)X(PhCl)(0.5) (X = PF6, AsF6), were carried out. The low-temperature physical properties of the title compounds are quite different from each other, although those at R.T. are very similar. The PF6 salt undergoes a spin-singlet transition around 170 K. On the other hand, the AsF6 salt shows a discontinuous transition of first order around 230 K, in association with an abrupt jump in the spin susceptibility. The AsF6 salt shows spin-gap behavior below 50 K, but it undergoes an antiferromagnetic transition at 14 K. The low-temperature electronic states of the title Compounds are discussed by microscopic point of view.

DOI： 10.1143/JPSJ.71.2022

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DOI： 10.1103/PhysRevB.65.024402

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

A new dihydrothiophene-extended BEDO-TTF (130) type donor, BO-HBDTT, was synthesized by a convenient method and gave metallic ClO4, BF4, and PF6 salts. Of these the ClO4 salt with beta" type donor arrangement showed two-dimensional metallic behavior and relatively narrow band width.

DOI： 10.1080/10587250210803

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

Magnetic investigation was carried out for quasi-one-dimensional organic conductors, (BDTFP)(2)X(PHCl)(0.5) (X=AsF6, PF6). They show Metal-Insulator transitions at low temperatures. To clarify the mechanism of the transitions, we performed ESR and NMR measurements. The low temperature electronic states of the title compounds are discussed by a microscopic point of view.

DOI： 10.1080/10587250210801

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We present the low-temperature crystal structures of (BDTFP)(2)PF6 and (BDTFP)(2)AsF6 below the phase transition temperatures (T-p). In the former compound, the c-axis is doubled, and the dimerized structure is therefore changed into a tetramerized structure. At the same time, a new charge-transfer transition appears at ca. 7000-8000 cm(-1). These two findings are consistent with the non-magnetic state below T-p. In the latter compound, on the other hand, the dimerized structure is maintained below T-p, and the AsF6 ion rotates along with the ca. 10degrees rotation of BDTFP. This structural change is the origin of the first-order phase transition to a paramagnetic state.

DOI： 10.1039/b202259c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

Crystal structures and electronic properties of [BO-HBDTT][PF6] and [BO-HBDTT]4[PF6] have been clarified. The donor packing patterns in these salts can be basically classified into α1-type, in which the donor stacks in the twisted overlap mode regarding the 1,3-dithiole rings. Intrastack intermolecular C-H⋯O contacts play an important role in the metallic nature of [BO-HBDTT]4[PF6].

DOI： 10.1246/cl.2001.514

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

2,5-Bis(4,5-ethylenedithio-1,3-dithiol-2-yliden)-2,5-dihydroselenophene (BEDT-BDTS), a selenophenoquinonoid-extended analogue of bis(ethylenedithio) tetrathiafulvalenes (BEDT-TTF), has been synthesized as a promising candidate for an electron-donating component of high T-c ,organic superconductors. BEDT-BDTS is air-stable and has a significantly enhanced electron-donating ability compared with that of BEDT-TTF. The molecular and crystal structures of BEDT-BDTS have been determined by single crystal X-ray analysis in which short intermolecular: S ... S contacts have been found in the side-by-side directions of the donor arrangements. A 1:1 TCNQ complex and a 3:1 I,(-)(3) radical cation salt of BEDT-BDTS have been obtained and proved to exhibit fairly high room temperature conductivities.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

2,5-Bis(4,5-ethylenedithio-1,3-dithiol-2-ylidene (BEDT-BDTS), a selenophenoquinonoid-extended analogue of bis(ethylenedithio) tetrathiafulvalenes (BEDT-TTF), has been synthesized as a promising candidate for an electron-donating component of high T-c organic superconductors. BEDT-BDTS is air-stable and has a significantly enhanced electron-donating ability compared with that of BEDT-TTF. The molecular and crystal structures of BEDT-BDTS have been determined by single crystal X-ray analysis in which short intermolecular S ... S contacts have been found in the side-by-side directions of the donor arrangements. A 1 : 1 TCNQ complex and a 3 : 1 I-3(-) radical cation salt of BEDT-BDTS have been obtained and proved to exhibit fairly high room temperature conductivities.

DOI： 10.1039/a703428h

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

2,5-Bis(1,3-dithiol-2-ylidene)-2,5-dihydroselenophene (BDTS) and its ethylenedithio (EDT-BDTS) and bis(ethylenedithio) (BEDT-BDTS) derivatives, novel extended donors with a central selenium atom, have been synthesized by convenient methods. Of these, EDT-BDTS and BEDT-BDTS having outer chalcogen atoms afforded highly conducting molecular complexes with TCNQ (sigma=13 Scm(-1) on a compressed pellet).

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Language：Japanese   Presentation type：Oral presentation (general)  

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Language：Japanese   Presentation type：Oral presentation (general)  

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Language：Japanese   Presentation type：Oral presentation (general)  

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Language：Japanese   Presentation type：Oral presentation (general)  

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Language：Japanese   Presentation type：Oral presentation (general)  

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Language：English   Presentation type：Poster presentation  

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Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Oral presentation (general)  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Oral presentation (general)  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Oral presentation (general)  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Oral presentation (general)  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Oral presentation (general)  

researchmap

Language：Japanese   Presentation type：Oral presentation (general)  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Oral presentation (general)  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap

Language：English   Presentation type：Poster presentation  

researchmap

Language：Japanese   Presentation type：Oral presentation (general)  

researchmap

Language：Japanese   Presentation type：Poster presentation  

researchmap