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

DOI： 10.1021/acsapm.3c00031

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

(Diamine)Pd(0)(dichlone)/NaBPh₄ systems have been revealed to be effective initiators for diazoacetate polymerization, yielding moderately syndiotactic polymers in moderate yields.

DOI： 10.1039/d2py01548j

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Publishing type：Research paper (scientific journal)  

Dispersion polymerization stabilized with poly(acrylic acid) has been performed for decades to produce polymer particles whose surfaces are modified with pH-responsive poly(acrylic acid) moieties. To improve stabilizer efficiency, poly(acrylic acid) block copolymers, in which a poly(acrylic acid) chain is attached to the terminus of a polystyrene or PMMA chain, were used as stabilizers for the dispersion polymerization of styrene or MMA. Compared with the poly(acrylic acid) homopolymer, polystyrene-block-poly(acrylic acid) was found to improve the controllable ranges of particle size and the carboxylic-acid-group surface density of the resulting polystyrene particles. Furthermore, we also investigated the effect of heterogeneity between the polymer species of the particle core and the attached polystyrene or PMMA chains in the poly(acrylic acid) block copolymers. Finally, we also examined the applicability of polystyrene-block-poly(acrylic acid) as a stabilizer and surface modifier for the dispersion polymerization of various monomers.

DOI： 10.1016/j.polymer.2022.125265

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Three new N-arylmaleimide-based Pd(0) complexes [Pd(N-phenylmaleimide)2(2,5-norbornadiene) (1), Pd(N-2,6-difluorophenylmaleimide)2(2,5-norbornadiene) (2), and Pd(N-2,6-difluorophenylmaleimide)2(dibenzylideneacetone) (3)] were prepared and used as an initiator in conjunction with NaBPh4[Pd(N-arylmaleimide)/NaBPh4system] for polymerization of diazoacetates. The Pd(N-arylmaleimide)/NaBPh4system polymerized a series of diazoacetates (ethyl, benzyl, and cyclohexyl diazoacetates) to yield polymers in moderate to good yield, particularly showing a high activity for cyclohexyl diazoacetate. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) analysis and other experimental observations revealed the incorporation of one N-arylmaleimide molecule coordinated on the Pd center into the α-chain end of the polymers obtained with the initiating system, indicating that the initiating species of the polymerization was generated by insertion of N-arylmaleimide into a Pd-Ph linkage, which was first formed by the reaction of the Pd(0) complex with NaBPh4, and that the initiating system would enable syntheses of α-chain-end-functionalized poly(alkoxycarbonylmethylene)s.

DOI： 10.1021/acs.macromol.2c00508

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Authorship：Corresponding author   Publishing type：Research paper (scientific journal)  

A new type of polyamine containing a 4,4′-diaminotriphenylamine-N,N′-diyl unit in the main chain was prepared by Ru-catalyzed polycondensation of a bis(diazocarbonyl) compound with 4,4′-diaminotriphenylamine, where the propagation is N-H insertion of a carbene-carbon atom generated from the diazocarbonyl group of the former monomer with N2 elimination. In the well-defined polyamines newly prepared in this study, the two primary amino groups in the diamine monomer remain as secondary amino groups in the polymer main chain, in contrast to the previously reported polymers prepared by polycondensation of the same diamine monomers, where the amino groups were incorporated into an amide or imide linkage. The resulting triphenyl amino framework in the polymer main chain possesses three amino groups, each of which can independently participate in the electrochemical process as a redox center with applied electrochemical potentials. The electrochromic properties of thin films and electrochromic devices of the polyamines were evaluated with cyclic voltammetry and spectroelectrochemistry, revealing that the polyamines indeed underwent an expected three-stage redox process.

DOI： 10.1039/d2py01118b

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© The Royal Society of Chemistry 2021. The reactivities of poly(alkoxycarbonylmethylene)s under basic conditions are described. The reactions of poly(ethoxycarbonylmethylene) (polyEDA′) and poly(benzyloxycarbonylmethylene) (polyBDA′) with a mixture of lithium diisopropylamide and trimethylsilyl chloride transformed a part of the repeating units (ca. 25 and 50 mol% for polyEDA′ and polyBDA′, respectively) into ketene silyl acetal frameworks. The ketene silyl acetal units were partially alkylated by the reaction with a mixture of tetrabutylammonium fluoride (TBAF) and an electrophile (methyl iodide and benzyl bromide), affording poly(substituted methylene)s with quaternary carbon atoms in the main chain, with the highest incorporation of 13 mol% being attained in the methylation of silylated polyBDA′. TBAF was found to effectively cleave carbon-carbon bonds in the main chain of polyEDA′ and polyBDA′ at room temperature for 1 h, yielding poly(alkoxycarbonylmethylene) oligomers with well-defined chain end structures with a much higher frequency of cleavage than that observed with their vinyl polymer counterparts, poly(alkyl acrylate)s.

DOI： 10.1039/d0py01486a

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

DOI： 10.1021/acs.macromol.0c01029

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

DOI： 10.1021/acsapm.0c00475

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

In the polymerization of diazoacetates initiated by pi-allylPd-based initiating systems, the effects of solvents, additives, and pi-allyl ligand structures on the polymerization behavior were investigated. As a result, the polymerization in the presence of pyridine or its derivatives as an additive was found to afford a polymer with relatively narrow molecular weight distribution compared to that with pi-allylPdCl alone. Furthermore, we have demonstrated that Pd complexes with pi-allyl ligands with a variety of substituents are capable of polymerizing diazoacetates in a similar manner to the parent unsubstituted pi-allylPdCl, and the tacticity of the resulting polymers is affected by the structure of the pi-allyl ligands.

DOI： 10.1039/c9py01654f

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© 2019, The Society of Polymer Science, Japan. The synthesis and characterization of organic-inorganic thermoresponsive poly(substituted methylene)s are described. Diazoacetates with oligo(ethylene glycol)-substituted cyclotriphosphazenes were synthesized, and the obtained products were employed as monomers for Pd-initiated polymerization to produce carbon–carbon main chain polymers bearing an oligo(ethylene glycol)-substituted cyclotriphosphazene on every main chain carbon atom. The resulting polymers with densely accumulated oligo(ethylene glycol) units around the polymer main chain showed lower critical solution temperature-type phase separation in an aqueous medium.

DOI： 10.1038/s41428-019-0247-7

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© 2020 American Chemical Society. The original synthetic strategy for a new type of poly(arylene vinylene) (PAV) is presented, where the C-C-bond-forming coupling of bis(alkoxycarbonyldiazomethyl)aromatic compounds is utilized as propagation. The strategy is unique in that the resulting PAVs have an alkoxycarbonyl group as an electron-withdrawing substituent on each vinylene carbon atom in the polymer main chain. Among the transition-metal catalysts examined in this study, RuCl(cod)Cp∗ (cod = 1,5-cyclooctadiene, Cp∗ = pentamethylcyclopentadienyl) is the most efficient, affording PAVs from a series of bis(alkoxycarbonyldiazomethyl)aromatic compounds with a high trans-C-C-forming selectivity of up to 90%. A PAV sample with a fluorenylene framework as an arylene moiety prepared by the Ru catalyst exhibited a hole mobility of 4 × 10-6 cm2 V-1 s-1.

DOI： 10.1021/acsomega.9b03408

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

© 2019, The Society of Polymer Science, Japan. Our recent studies on the polymerization of diazocarbonyl compounds to afford functional polymers are reviewed. In the first part of this article, the Pd-mediated polymerization of diazoacetates is described. Various functionalized diazoacetates with ester substituents were prepared and polymerized with Pd-based initiating systems to yield poly(substituted methylene)s (PSMs) with functional groups on each carbon atom in the main chain. The physical and chemical properties of the resulting functionalized PSMs were examined relative to those of their vinyl polymer counterparts [poly(substituted ethylene)s] possessing the same functional groups on every other carbon atom, and enhanced properties due to the effects of the dense packing of the functional groups in the PSMs were observed in some examples. The second part of this report summarizes our recent results on the polycondensation of bifunctional diazocarbonyl compounds as monomers. Three successful examples, namely, (1) the synthesis of well-defined unsaturated polyesters by the transition metal-catalyzed, single-component polycondensation of bis(diazoacetate)s, (2) the preparation of a new type of aromatic polyamine by the polycondensation of bis(diazoacetate)s with aromatic diamines, and (3) the multicomponent polycondensation of bis(diazocarbonyl) compounds affording an unprecedented acid-degradable polymer, poly(β-keto enol ether), are described.

DOI： 10.1038/s41428-019-0271-7

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

Copyright © 2019 American Chemical Society. For polymerization of alkyl diazoacetates, the combination of a Pd complex bearing 1,4-naphthoquinone (NQ) or its derivatives as a ligand and borate, NaBPh4, was found to be an efficient initiating system. The polymerization of ethyl diazoacetate by a Pd(0) complex having two NQ molecules [Pd(nq)2] with NaBPh4 proceeded to give poly(ethoxycarbonylmethylene)s with a relatively high molecular weight (up to Mn = 36 kDa) in good yield (â 70%). This initiating system was also effective for polymerizing other diazoacetates, benzyl and cyclohexyl diazoacetates. In addition, in the presence of NaBPh4, a novel Pd(II) complex bearing an anionic naphthoquinonyl ligand derived from 2,3-dichloro-1,4-naphthoquinone (dichlone), [Pd(cod)(Cl-nq)Cl] (cod = 1,5-cyclooctadiene), which was newly prepared by treatment of a Pd(0) precursor, Pd2(dba)3·CHCl3 [dba = (E,E)-dibenzylideneacetone], with COD and dichlone, was capable of affording poly(alkoxycarbonylmethylene)s with much higher stereoregularity compared to the previously reported Pd-based initiating systems, despite a rather low polymer yield (â 20%). For both Pd(nq)-based initiating systems, Pd-Ph species generated by transmetalation with NaBPh4 were responsible for the initiation of diazoacetates based on MALDI-TOF-MS analyses of the resulting polymers, and naphthoquinones played unique important dual roles as both an oxidant and an anionic ligand for generating the active Pd(II) species.

DOI： 10.1021/acs.macromol.9b00857

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

Copyright © 2019 American Chemical Society. Rh-catalyzed three-component polycondensation of bis(diazoketone), bis(1,3-diketone), and tetrahydrofuran (THF) yielded poly(β-keto enol ether) via a simultaneous insertion of a diazo-bearing carbon atom of bis(diazoketone) with N2 elimination and a ring-opened THF into OH of an enol form of a 1,3-diketone moiety of bis(1,3-diketone). The β-keto enol ether linkage of the polymer can be efficiently cleaved under mild acidic conditions to afford a combination of two types of well-defined low molecular weight components in high yield. The degradation can indeed proceed even with trace of acid in CDCl3 solution in an NMR tube, while the polymer structure remained intact in a DMSO-d6 solution, demonstrating the high sensitivity of the β-keto enol ether linkage to acidic conditions. ©

DOI： 10.1021/acs.macromol.9b00653

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© 2018 Elsevier Ltd Recent progress on polymerization of diazoacetates is described. Polymerization of diazoacetates has attracted much attention as an efficient method for C1 polymerization, which constructs C-C main chains from one carbon units. A variety of initiating systems consisting of Cu, Pd, B, and microwave activation have been revealed to afford polymers from diazoacetates with relatively low molecular weight. Rh-initiated polymerization of diazoacetates is remarkable for its ability of affording high molecular weight polymers in a stereospecific manner. The essence of the active species and mechanistic details for the Rh-initiated polymerization have been clarified by a combination of experimental and theoretical investigations. Copolymerization of diazoacetate with (CH2)n-affording monomers yielded unique polymer structures comparable to those of ethylene-acrylate copolymers. A series of postpolymerization modification approaches have been examined for the polymers obtained by the Rh-initiated polymerization. Some Pd-based initiating systems have been revealed to be effective for the polymerization of diazoacetates. A variety of substituents were introduced as ester substituents of diazoacetates, and they were polymerized by the Pd-based initiating systems. The effect of dense packing of the substituents on properties of the resulting polymers were examined in comparison to their vinyl polymer counterparts, and the enhanced properties in poly(substituted methylene)s were indeed observed in a number of examples.

DOI： 10.1016/j.polymer.2018.11.049

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

DOI： 10.1016/j.polymer.2018.10.040

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

The excited-state dynamics of pyrene incorporated into poly(substituted methylene)s is investigated by picosecond time-resolved fluorescence spectroscopy and femtosecond time-resolved near-IR absorption spectroscopy in the 900-1400 nm region. The pyrene rings in poly (substituted methylene)s are photoexcited to the monomer excited state immediately after UV irradiation, followed by prompt excimer formation with time constants of a few picoseconds to a few hundred picoseconds. The excimer formation in poly(substituted methylene)s proceeds with much shorter time constants than that in pyrene-incorporated polyacrylates, vinyl polymer counterparts with the same side-chain structures, indicating the presence of stronger electronic interaction between the pyrene rings in poly(substituted methylene)s. The effects of every methylene substitution hold when each pyrene ring is connected to the polymer backbone with a monomethylene linker, while the effects are observed only weakly when a tetramethylene linker is employed. The results demonstrate the effectiveness of every methylene substitution in the prompt excimer formation of pyrene connected to the polymer backbone either directly or with the monomethylene linker.

DOI： 10.1021/acs.macromol.8b01060

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

© 2017 American Chemical Society. Pd-initiated polymerization of fluorine (F)-containing alkyl and phenyl diazoacetates is described. Polymerization of 2,2,2-trifluoroethyl diazoacetate [Et(CF3)DA] with π-allylPdCl afforded a C-C main chain polymer bearing a 2,2,2-trifluoroethoxycarbonyl group on each main chain carbon atom. The polymer showed upper critical solution temperature (UCST)-type phase separation in multiple common organic solvents with differing polarities. Although homopolymerization of 3,3,4,4,5,5,6,6,6-nonafluorohexyl diazoacetate [Hex(C4F9)DA] with a higher fluorine content yielded an insoluble product, copolymerization of Hex(C4F9)DA with non-fluorinated ethyl diazoacetate (EDA) proceeded homogeneously to give a soluble F-containing copolymer. Polymerization of a series of F-containing phenyl diazoacetates was also conducted with the same initiator, giving poly[(F-containing aryloxycarbonyl)methylene]s, which showed significant solubility differences depending on the substitution pattern of F atoms on the phenyl ring. Efficient postpolymerization modification of poly[(F-containing aryloxycarbonyl)methylene]s was achieved with a primary amine, affording a polymer with both a five-membered cyclic imide structure and an N-alkylcarbamoyl group in its side chains.

DOI： 10.1021/acs.macromol.7b01964

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

The cyclotriphosphazene-substituted diazoacetate homopolymer (polyPNDA′) (PNDA′ = hexaphenoxy-substituted phosphazene-containing methylene) and a novel poly(substituted methylene) block copolymer, polyPNDA′-block-poly(hexyloxycarbonylmethylene) (polyPNDA'-b-polyHDA′), were synthesized, and the self-assembly behavior of these polymers was studied in detail. A hexagonally packed aggregated structure was observed in the self-assembled structure of polyPNDA′, whereas a lamellar structure was observed in the microphase-separated nanoassembly of polyPNDA′-b-polyHDA′. These results indicate that a hierarchical structure composed of highly regular polyPNDA′ nanoaggregates and the long-range microphase-separated polyPNDA′ and polyHDA′ domains had formed.

DOI： 10.1021/acsmacrolett.7b00789

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

Transition-metal-catalyzed N-H insertion of a diazocarbonyl compound is applied for polycondensation for the first time to give a new type of aromatic polyamine. The well-defined polyamines were obtained by [RuCl2(p-cymene)](2)-catalyzed reaction of diethyl1,4-phenylenebis(diazoacetate) with dianilines bearing a variety of linkers between two aniline units. The polycondensation proceeded at 30 degrees C in CH2Cl2 with 5.0 mol % of the Ru metal to [NH2 or N-2 = C] to afford the products with M-n = 6400-28 300 in moderate to high yield. Ethoxycarbonyl groups located at an adjacent position to NH imparted solubility to the polyamines, and their glass transition temperatures can be varied depending on the linker structure in a range of 88-173 degrees C.

DOI： 10.1021/acs.macromol.7b01994

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

The initiating ability of a new system, amidinate/Pd, for the polymerization of diazoacetates is described. The system is effective in affording relatively high number-average molecular weight (M-n) polymers from ethyl diazoacetate (EDA, e.g., M-n = 45 100, 44% yield) and methyl diazoacetate (MDA, e.g., M-n = 26 200, 56% yield) in moderate yield. The polymerization of n-hexyl diazoacetate (nHDA) and benzyl diazoacetate (BDA) by the amidinate/Pd system yields high M-n polymers (M-n = ca.100 000), although the yield was below 10%. The system is also effective in the copolymerization of EDA with nHDA, BDA, and cyclohexyldiazoacetate (cHDA), affording high M-n copolymers in moderate yield. NMR spectra of the products obtained with the system suggest that the polymerization proceeds with significantly higher stereoregularity compared to that with previously reported Pd-based initiating systems.

DOI： 10.1039/c7py00816c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCI LTD  

A novel poly(L-lysine) macromonomer was successfully prepared via a click reaction between vinyl benzyl azide and propargyl-terminated poly(L-lysine), and it was used as a functional stabilizer for the dispersion polymerization of styrene; narrowly distributed polystyrene particles were produced as a result, onto which cationic poly(L-lysine) chains were grafted. The resulting particles exhibited a pH responsive dispersion behavior in aqueous solutions due to the properties of the poly(L-lysine) chains at the particle surface. It was found that the particle size and the surface density of the resultant particles could be varied by tuning the concentrations of the macromonomer, styrene, and initiator used in the initial solution of the dispersion polymerization. The poly(L-lysine) macromonomer was also found to be effective when used as a stabilizer for the dispersion polymerization of both methyl methacrylate and a styrene/acrylonitrile mixture. (C) 2017 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.polymer.2017.04.077

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

Cyclopolymerization of bis(diazocarbonyl) compounds is described for the first time. By choosing appropriate reaction conditions and monomer structures, the cyclopolymerization of bis(diazoacetate)s efficiently proceeded to give carbon-carbon main chain cyclopolymers with well-defined structures, as confirmed by MALDI-TOF-MS analyses. The products are a new kind of cyclopolymer with respect to polymer structure: there exists no free methylene in the sp(3)-carbon-based polymer backbone in contrast to conventional cyclopolymers prepared from divinyl compounds, which inevitably have free methylenes in and between cyclic units in their polymer backbones. The resulting cyclopolymers with closely aligned cyclic units along the polymer backbone showed a much higher glass transition temperature compared to the corresponding polymers without cyclized repeating units.

DOI： 10.1021/acs.macromol.6b01809

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Language：Japanese   Publishing type：Research paper (scientific journal)  

CiNii Books

J-GLOBAL

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

A new carbon-carbon main chain polymer with N-phenyl-2,6-dimethoxybenzamide on its each main chain carbon atom is prepared by Pd-initiated polymerization of diazoacetate containing the benzamide group, and the Li ion conductivity of the polymer doped with lithium bis(trifluoromethylsulfonyl)imide is evaluated along with its vinyl polymer counterparts with the same benzamide substituent. Although the expected high ion conductivity at low temperatures derived from a unique ion transport mechanism based on the bond rotation in the benzamide moiety reported in a literature is not observed, it is revealed that the dense packing of the benzamide group along the polymer main chain results in the enhanced ion conductivity. In addition, investigation of the correlation between ion conductivity and glass transition temperature of these solid polymer electrolytes (SPEs) reveals that other ion transport mechanism would operate in the benzamide containing SPEs than that derived from segmental motion of polymer chains observed in PEO-based SPEs. (C) 2016 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.ssi.2016.05.001

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

Pd-initiated polymerization and oligomerization of diazo compounds containing a dialkoxyphosphinyl group are described. Polymerization of 2-dialkoxyphosphinylethyl diazoacetates with pi-allylPdCl-based initiating systems afforded C-C main chain polymers bearing phosphonate on each main chain carbon atom. The quantitative transformation of the side chain phosphonate to phosphonic acid resulted in the formation of water soluble polymers having the acid groups accumulated around their main chains, although the carbonyl ester linkage in the side chain was cleaved via intramolecular acid-assisted hydrolysis in water at 80 degrees C. Pd-initiated oligomerization of diethyl diazomethylphosphonate yielded an oligomeric product bearing diethoxyphosphiny groups directly attached to its main chain carbons, with unexpected incorporation of azo group in the main chain framework. Hydrolysis of the phosphonate of the oligomer afforded a water-soluble product, which was revealed to show higher proton conductivity than poly(vinylphosphonic acid) under certain conditions. (C) 2016 Wiley Periodicals, Inc.

DOI： 10.1002/pola.28030

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCI LTD  

A novel macromonomer composed of poly(a-L-glutamic acid) was used as a stabilizer for dispersion polymerization of styrene in DMF-water medium with AIBN initiator, giving narrowly-distributed functional polystyrene particles on which the poly(a-L-glutamic acid) was grafted. The resultant particles had 0.54-2.12 mm in size and 0.2-2.6 residue/nm(2) in surface density and showed a pH-responsive colloidal behavior associated with a helix-coil transformation of the surface poly(a-L-glutamic acid). Not only the particle size but also the surface density were controlled with macromonomer concentration, macromonomer length, DMF composition, and styrene concentration, while no consistent trend for AIBN concentration was observed. A gel-permeation-chromatography curve of the particles was separated into three components. We tentatively identify the origin of each component and propose a possibility that unstable particles, which were generated even after the growing particles were stabilized, took an important role in particle growth and size distribution of the resultant particles. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.polymer.2015.06.022

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

Pd-initiated polymerization of alkyl diazoacetates as an effective methodology to prepare carbon-carbon (CC) main chain polymers bearing a substituent on every main chain carbon is described. (NHC)Pd/borate (NHC=N-heterocyclic carbene) systems are efficient at affording high M-n polymers. pi-AllylPdCl-based systems can initiate the polymerization with the number of polymer chain per Pd ratios over 1.0 because of occurrence of chain transfer, capable of affording relatively low M-n polymers in high yield. Initiation and termination mechanisms have been proposed for the latter initiating systems, based on the detailed MALDI-TOF-MS analyses of the low M-n products.

DOI： 10.1002/masy.201400007

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

Polymerization of cyclophosphazene-containing diazoacetates was carried out using a (eta(3)-C3H5) PdCl-based initiating system to produce sp(3)-sp(3) carbon-carbon main chain polymers bearing a cyclophosphazene-containing ester group on every main chain carbon atom. The obtained polymers had very narrow molecular weight distributions in contrast to the case of other alkyl or aryl diazoacetates reported previously, suggesting that the polymerization of cyclophosphazene-containing diazoacetates proceeded in a controlled manner without apparent side reactions, which was confirmed by MALDI-TOF-MS analysis. In addition, block copolymers with a well-defined structure were successfully synthesized. This is the first report on controlled polymerization of diazoacetates to afford narrow molecular weight distribution polymers. Furthermore, thermogravimetric analysis was conducted to reveal that the resulting polymers had a higher thermal stability compared to the vinyl polymer counterparts.

DOI： 10.1039/c5py00532a

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

Synthesis and characterization of polymers with densely-grafted oligo(ethylene glycol)s (OEGs) are described. Polymerization of OEG-containing diazoacetates with (eta(3)-C3H5)PdCl-based initiating systems afforded C-C main chain polymers bearing OEGs on each main chain carbon atom. The polymers with a short OEG side chain showed a lower critical solution temperature-type phase separation in an aqueous medium; the transition temperatures were higher than those of the corresponding vinyl polymers with the same oxyethylene chain length. In addition, the Li-ion conductivity was examined to reveal that the polymers with densely-grafted OEGs showed higher values than the corresponding vinyl polymers, despite the fact that no significant difference in the glass transition temperature was observed between the two types of polymers.

DOI： 10.1039/c5py01378j

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：SOC POLYMER SCIENCE JAPAN  

We describe the polymerization of a variety of diazocarbonyl compounds initiated with Pd complexes. Relatively low molecular weight polymers (M-n = ca. 2000) were obtained by the polymerization of diazoacetates, diazoketones, and diazoacetamides initiated with PdCl2. On the other hand, the polymerization of diazoacetates by (NHC)Pd/borate and pi-allyl-PdCl-based systems can afford high molecular weight polymers (M-n > 10000). Chain-end structure analyses by using MALDI-TOF-MS was used to elucidate initiation and termination mechanisms for the pi-allyl-PdCl-based systems. Polymerization of hydroxy-containing diazoacetates resulted in the formation of unique polymers with densely accumulated hydroxy groups around their C-C main chains.

DOI： 10.1295/koron.2014-0100

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCI LTD  

A block copolymer composed of polystyrene and poly(alpha-L-lysine hydrobromide) (PLL) segments was used as a stabilizer for dispersion polymerization of styrene in water-methanol medium to give narrowly-distributed polystyrene particles in the size range from 0.36 to 1.09 mu m, on which the PLL segment was grafted with a surface density of 0.2-3.4 L-lysine residue/nm(2). We investigated effects of polymerization time, stabilizer concentration, segmental composition of the block copolymer, and composition of the medium on surface structure and particle size of the affording particles. Interestingly, we obtained an experimental evidence that the surface density of the PLL clearly depends on structural parameters of the stabilizer and various polymerization conditions. Based on the dependence, it was possible to control the surface density of the narrowly-distributed particles within the range between the minimum and the maximum density limits of the graft chain by changing the structure of the stabilizer and polymerization conditions. Conformation of the PLL, which underwent a helix-coil transformation with an increase in water composition of the medium, had a strong effect on the surface structure, the size, and property of the resulting particles. Further modification of the particle surface was possible by utilizing the amino groups in the PLL graft. (C) 2014 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.polymer.2014.06.069

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

Two types of polymerization of hydroxy-containing diazoacetates are described. The polymerization of hydroxy-containing diazoacetates using palladium complexes proceeded successfully under chain-growth mechanism even without a protecting group to give C-C main chain polymers bearing a hydroxy-containing ester substituent on each carbon of the backbone. The resulting polymers had a slightly branched structure due to chain transfer reaction with the hydroxy groups, while the polymers obtained by polymerization of silyl-protected diazoacetates and subsequent deprotection had a completely linear structure. The hydroxy-containing polymers with an appropriate hydrophilic/hydrophobic balance showed a lower critical solution temperature-type phase separation in an aqueous medium. On the other hand, the polymerization of hydroxy-containing diazoacetates using InCl3 as a catalyst proceeded under step-growth mechanism to give oligomers having a distinct repeating unit (ester-ether), where a new ether bond was generated through O-H insertion reaction of diazocarbonyl groups into hydroxy groups.

DOI： 10.1021/ma500783b

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

A variety of aliphatic- and aromatic-type unsaturated polyesters (UPs) were prepared by transition-metal-catalyzed single-component polycondensation of bis(diazoacetate)s under a mild condition. With the second-generation Grubbs catalyst, the polycondensation proceeded exclusively through an intermolecular highly cis-selective C=C forming coupling of diazo-bearing carbons with N-2 release, giving well-defined UPs. The cis-C=Cs of the resulting polymers could be isomerized quantitatively into trans-C=Cs with a catalytic amount of diethylamine. Additionally, other metal complexes, the first-generation Grubbs catalyst, rhodium(II) acetate, and copper(II) acetylacetonate, also produced UPs from the bis(diazoacetate)s, with lower stereoselectivities, although an unexpected carbene oligomerization of the monomers partially occurred along with the C=C bond-forming coupling.

DOI： 10.1021/ma401047x

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Radical copolymerization behavior of alkyl cyclobutenecarboxylate-derivatives 4-6 and related norbornene-derived compounds 79 is described. A variety of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework (46) were prepared by [2 + 2] cycloaddition of five, six, and eight-membered cycloolefins with alkyl propiolates [alkyl = Me, 2-hydroxyethyl, and 3--butyrolactonyl (-BL)]. The fused cyclobutenecarboxylates 46 were radically copolymerized with n-butyl acrylate (nBA) to afford random copolymers, and terpolymerized with alkyl methacrylates with bulky ester groups [alkyl = -BL and 3-(3-methyladamantyl)]. The cyclobutane-containing bicyclic framework incorporated in the resulting polymer backbone contributes to raising Tg of resulting copolymers. Similar results were obtained when a mixture of related norbornene-derived compounds were used as monomers with an apparently enhanced Tg-raising effect in the copolymerization with nBA. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 27162724

DOI： 10.1002/pola.26668

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Pd-mediated polymerization of 1-pyrenylmethyl diazoacetates affords poly(1-pyrenylmethoxycarbonylmethylene) (poly4′), whose CC main chain is tightly surrounded by pyrene groups. The intensity ratio of excimer emission to monomer emission (IE/I M) of poly4′ was more than 20 times higher than that of its vinyl polymer counterpart of poly(1-pyrenylmethyl methacrylate) (polyPyrMA), clearly demonstrating much higher efficiency for excimer formation in poly4′, because of the tight arrangement of the pyrene groups around the main chain. Copyright © 2012 Wiley Periodicals, Inc.

DOI： 10.1002/pola.26480

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

A series of poly(2-methoxyethyl vinyl ether)s with narrow molecular weight distributions and with perfectly defined end groups of varying hydrophobicities was successfully synthesized by base-assisting living cationic polymerization. The end group was shown to greatly affect the temperature-induced phase separation behavior of aqueous solutions (lower critical solution temperature-type phase separation) or organic solutions (upper critical solution temperature-type phase separation) of the polymers. The cloud points were also influenced largely by the molecular weight and concentration of the polymer. (c) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

DOI： 10.1002/pola.26219

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Graft copolymers with various combinations of backbones and branch chains were synthesized using a new vinyl monomer containing an acetal pendant group in conjunction with a combination of metal halides by selective living cationic polymerization without any functional group transformations. Copyright © 2012 Wiley Periodicals, Inc.

DOI： 10.1002/pola.26186

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

Polymerization of ethyl and benzyl diazoacetates (EDA and BDA) initiated with pi-allylPdCl-based systems [pi-allylPdCl/NaBPh4, pi-allylPdCl/NaBAr4F (Ar-F = 3,5-{CF3}(2)C6H3), and pi-allylPdCl] is described. Initiation efficiencies of the pi-allylPdCl-based systems are much higher than those of the previously reported (NHC)Pd/borate (NHC = N-heterocydic carbene) systems, and the new systems are capable of polymerizing the alkyl diazoacetates at low temperatures (0 similar to -20 degrees C), where the (NHC)Pd/borate systems cannot initiate the polymerization. MALDI-TOF-MS analyses of the polymers obtained from EDA provide information for the chain-end structures of the polymers, based on which initiation and termination mechanisms are proposed. Interestingly, EDA polymerization by the pi-allylPdCl-based systems in the presence of alcohols (EtOH, nPrOH, and nBuOH) or water was found to afford RO- or HO-initiated polymers as major products, as confirmed by MALDI-TOF-MS analyses.

DOI： 10.1021/ma3013527

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Various types of fluorine-containing star-shaped poly(vinyl ether)s were successfully synthesized by crosslinking reactions of living polymers based on living cationic polymerization. Star polymers with fluorinated arm chains were prepared by the reaction between a divinyl ether and living poly(vinyl ether)s with fluorine groups (C4F9, C6F13, and C8F17) at the side chain using cationogen/Et1.5AlCl1.5 in a fluorinated solvent (dichloropentafluoropropanes), giving star-shaped fluorinated polymers in high yields with a relatively narrow molecular weight distribution. The concentration of living polymers for the crosslinking reaction and the molar feed ratio of a bifunctional vinyl ether to living polymers affected the yield and molecular weight of the star polymers. Star polymers with block arms were prepared by a linking reaction of living block copolymers of a fluorinated segment and a nonfluorinated segment. Heteroarm star-shaped polymers containing two- or three-arm species were synthesized using a mixture of different living polymer species for the reaction with a bifunctional vinyl ether. The obtained polymers underwent temperature-induced solubility transitions in various organic solvents, and their concentrated solutions underwent solgel transitions, based on the solubility transition of a thermoresponsive fluorinated segment. Furthermore, a slight amount of fluorine groups were shown to be effective for physical gelation when those were located at the arm ends of a star polymer. (C) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

DOI： 10.1002/pola.25922

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Poly[(2-ethoxy) ethoxy ethyl vinyl ether] (poly(EOEOVE)) is a representative thermoresponsive polymer in aqueous solution for which the time constants of the phase separation (PS) are determined with high accuracy. It is revealed that the PS dynamics of the polymer are entirely different from those of the poly(N-isopropylacrylamide) (PNIPAM) system, which is an alternative representative thermoresponsive polymer. Poly(EOEOVE) exhibits complicated PS behavior that is described using double exponential functions. The PS of poly(EOEOVE) is much faster than the PS of PNIPAM in aqueous solutions and becomes faster with increasing concentration of the polymer. PS behavior that is particular to the present system is successfully understood within the framework of the aggregation mechanism.

DOI： 10.1002/macp.201100540

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Partially fluorinated poly(vinyl ether)s with C4F9 and C6F12H groups in the side chain were synthesized via living cationic polymerization in the presence of an added base in a fluorine-containing solvent, dichloropentafluoropropanes. For comparison, the polymerization of vinyl ether monomers with C2F5 and C6F13 groups and nonfluorinated monomers were also carried out. The characterization of the product polymers using size exclusion chromatography with a fluorinated solvent as an eluent indicated that all polymers had narrow molecular weight distributions (M-w/M-n similar to 1.1). Interestingly, the moderately fluorinated polymers with C4F9 exhibited upper critical solution temperature-type phase separation in various organic solvents with wide-ranging polarities, whereas highly fluorinated polymers with C6F13 are insoluble in nonfluorinated solvents. Polymers with C4F9 groups exhibited temperature dependent solubility transitions not only in common organic solvents (e.g., toluene, chloroform, tetrahydrofuran, and acetone) but also in perfluoro solvents [e.g., perfluoro(methylcyclohexane) and perfluorodecalin]. On the other hand, the solubility of polymers with C6F12H showed completely different from that of polymers with C6F13, despite their similar fluorine content. In addition, various types of fluorinated block copolymers were prepared in a living manner. The block copolymers with a thermosensitive fluorinated segment underwent temperature-induced micellization and sol-gel transition in various organic solvents. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 2051-2058, 2011

DOI： 10.1002/pola.24634

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

Living cationic polymerization of fluorine-containing vinyl ethers [CH2=CH-O-C2H4-O-C3H6-CnF2n+1: 5FVE (n = 2), 13FVE (n = 6)] was investigated in various solvents with a CH3CH(OiBu)OCOCH3/Et1.5AlCl1.5 initiating system in the presence of an added base. 5FVE was polymerized quantitatively in toluene at 0 degrees C, and the obtained polymers had predetermined molecular weights with narrow molecular weight distributions (M-w/M-n < 1.1). On the other hand, for the polymerization of 13FVE, the product polymers precipitated due to their extremely poor solubility in nonfluorinated organic solvents. Therefore, fluorinated solvents such as hydrochlorofluorocarbons, hydrofluorocarbons, hydrofluoroethers, or alpha,alpha,alpha-trifluorotoluene, as-yet uninvestigated for cationic polymerization, were employed. In these solvents, living polymerization was achieved even with 13FVE, yielding well-defined polymers (M-w/M-n < 1.1, by size exclusion chromatography using a fluorinated solvent as an eluent). The solvents were also shown to be good for living polymerization of isobutyl vinyl ether. The obtained fluorine-containing polymers underwent temperature-responsive solubility transitions in organic solvents. Poly(5FVE) showed sensitive upper critical solution temperature (UCST)-type phase separation behavior in toluene. Copolymers of 13FVE and isobutyl vinyl ether showed UCST-type phase separation in common organic solvents with different polarities depending on their composition, while a homopolymer of 13FVE was insoluble in all nonfluorinated organic solvents. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 1174-1182, 2011

DOI： 10.1002/pola.24534

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCI LTD  

For development of tumor-specific chemotherapy, we designed liposomes with temperature-triggered drug release and magnetic resonance imaging (MRI) functions. We prepared multi-functional liposomes by incorporating thermosensitive poly(2-ethoxy(ethoxyethyl)vinyl ether) chains with a lower critical solution temperatures around 40 degrees C and polyamidoamine G3 dendron-based lipids having Gd(3+) chelate residues into pegylated liposomes. These stable doxorubicin (DOX)-loaded liposomes retained DOX in their interior below physiological temperature but released DOX immediately at temperatures greater than 40 degrees C. They exhibited excellent ability to shorten the longitudinal proton relaxation time. When administered intravenously into colon 26 tumor-bearing mice, accumulated liposomes in tumors increased with time, reaching a constant level 8 h after administration by following T(1)-weighted MRI signal intensity in tumors. Liposome size affected the liposome accumulation efficiency in tumors: liposomes of about 100 nm diameter were accumulated more efficiently than those with about 50 nm diameter. Tumor size also affected accumulation: more efficient accumulation occurred in larger tumors. Tumor growth was strongly suppressed when liposomes loaded with DOX were administered intravenously into tumor-bearing mice and the tumor was heated mildly at 44 degrees C for 10 min at 8 h after administration. Multi-functional liposomes having temperature-triggered drug release and MRI functions might engender personalized chemotherapy, providing efficient patient-optimized chemotherapy. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.biomaterials.2010.10.050

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This study demonstrated significant effects of a terminal structure of thermosensitive polymers on the clouding points of the polymers in water. Thermosensitive polymers with various end-functional groups were synthesized using a functionalized initiator (1) via living cationic polymerization in the presence of an added base. The clouding points of aqueous solutions of the polymers increased or decreased with decreasing molecular weight for hydrophilic or hydrophobia terminal groups, respectively. In addition, the terminal effect was amplified in a micelle, derived from an amphiphilic diblock copolymer with a terminal group at the end of the hydrophilic chain.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

We have demonstrated that poly (vinyl ether)s with oxyethylene pendants underwent highly sensitive LCST-type phase separation in water. In addition, the sensitivity and the clouding point were governed by primary structures of polymers. In this study, we synthesized thermosensitive polymers with various end-functional groups via living cationic polymerization in the presence of an added base, and examined their thermosensitive behavior in water. For polymers with octadecyl terminals, the clouding point decreased sharply with decreasing their molecular weights, whereas the corresponding polymers without the terminal function induced an increase in clouding point as the molecular weight decreased.

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Language：Japanese   Publishing type：Article, review, commentary, editorial, etc. (other)  

J-GLOBAL

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J-GLOBAL

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Language：English   Publisher：American Chemical Society  

A variety of fluorine-containing polymers of vinyl ethers with well-defined structures were synthesized by base-assisting living cationic polymerization. Well-controlled reactions were achieved in various fluorinated solvents, which had not been examined as solvents for cationic polymerization. Excellent living nature of the reactions allowed precision synthesis of block and star-shaped polymers with controlled sequences. The resulting fluorinated polymers with appropriate fluorine content underwent highly sensitive upper critical solution temperature (UCST)-type phase separation in organic solvents with a range of polarities including perfluoro versions. The unique solubility permitted thermoresponsive physical gelation with solutions of star block or heteroarm star polymers. © 2012 American Chemical Society.

DOI： 10.1021/bk-2012-1106.ch005

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Language：English   Publishing type：Research paper, summary (international conference)   Publisher：AMER CHEMICAL SOC  

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中国四国支部長賞を受賞

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Language：English   Presentation type：Oral presentation (invited, special)  

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Presentation type：Oral presentation (invited, special)  

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Language：Japanese   Presentation type：Poster presentation  

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Language：Japanese   Presentation type：Poster presentation  

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Language：Japanese   Presentation type：Oral presentation (general)  

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Language：Japanese   Presentation type：Poster presentation  

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Language：Japanese   Presentation type：Poster presentation  

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Language：Japanese   Presentation type：Poster presentation  

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Presentation type：Poster presentation  

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Language：Japanese   Presentation type：Poster presentation  

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Presentation type：Poster presentation  

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Language：English   Presentation type：Oral presentation (general)  

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Presentation type：Poster presentation  

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Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Presentation type：Poster presentation  

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Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Presentation type：Poster presentation  

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Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Language：Japanese   Presentation type：Poster presentation  

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Language：Japanese   Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Language：Japanese   Presentation type：Poster presentation  

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Presentation type：Oral presentation (invited, special)  

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Language：Japanese   Presentation type：Poster presentation  

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Presentation type：Oral presentation (invited, special)  

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Presentation type：Oral presentation (general)  

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Presentation type：Poster presentation  

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Presentation type：Poster presentation  

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Presentation type：Poster presentation  

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Presentation type：Poster presentation  

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Language：English   Presentation type：Oral presentation (invited, special)  

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Presentation type：Poster presentation  

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Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Presentation type：Poster presentation  

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Presentation type：Oral presentation (general)  

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Presentation type：Poster presentation  

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Presentation type：Poster presentation  

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Presentation type：Oral presentation (general)  

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Presentation type：Oral presentation (general)  

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Applicant：ダイキン工業株式会社, 国立大学法人大阪大学

Application no：特願2010-000817  Date applied：2010.1

Announcement no：特開2011-140536  Date announced：2011.7

Patent/Registration no：特許第5684477号  Date issued：2015.1

J-GLOBAL

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Applicant：ダイキン工業株式会社, 国立大学法人大阪大学

Application no：特願2009-213733  Date applied：2009.9

Announcement no：特開2011-063660  Date announced：2011.3

Patent/Registration no：特許第5485626号  Date issued：2014.2

J-GLOBAL

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Applicant：ダイキン工業株式会社, 国立大学法人大阪大学

Application no：特願2009-213734  Date applied：2009.9

Announcement no：特開2011-063661  Date announced：2011.3

Patent/Registration no：特許第5558765号  Date issued：2014.6

J-GLOBAL

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Applicant：ダイキン工業株式会社, 国立大学法人大阪大学

Application no：特願2009-213734  Date applied：2009.9

Announcement no：特開2011-063661  Date announced：2011.3

J-GLOBAL

researchmap

Applicant：ダイキン工業株式会社, 国立大学法人大阪大学

Application no：特願2009-213733  Date applied：2009.9

Announcement no：特開2011-063660  Date announced：2011.3

J-GLOBAL

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