Synthesis and Properties of Regioregular Polythiophene Bearing Cyclic Siloxane Moiety at the Side Chain and the Formation of Polysiloxane Gel by Acid Treatment of the Thin Film

Ogura, Tadayuki; Kubota, Chihiro; Suzuki, Toyoko; Okano, Kentaro; Tanaka, Norikazu; Matsumoto, Takuya; Nishino, Takashi; Mori, Atsunori; Okita, Takumi; Funahashi, Masahiro

doi:10.1246/cl.190139

Cited by 13 publications

(13 citation statements)

References 53 publications

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“…Table 1 The obtained copolymers were then subjected to measurements of optoelectronic properties as a thin-film on a quartz or the ITO electrode. 49 As shown in Fig 5, the film of 12 (m = 3.7; n = 1) as deposited showed λmax of 520 nm while transparent at higher than ca. 700 nm (NIR region).…”

Section: Synthesis and Characterization Of A Polyacetylene Derivativementioning

confidence: 79%

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Thermally Induced Self-Doping of π-Conjugated Polymers Bearing a Pendant Neopentyl Sulfonate Group

et al. 2020

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Regioregular Head-to-tail (HT)-type polythiophene was synthesized by deprotonative nickel-catalyzed cross-coupling polymerization of 2-chlorothiophene bearing neopentyl benzenesulfonate group at the 3-position. The obtained HT-regioregular polymer was found dissolved in chloroform or THF, while it turned to water soluble upon heating the polymer 2 at 185 °C for 10 min by the liberation of the protected neopentyl group. The thin-film of the polymer showed remarkable improvement of the conductivity ca. 10 3 times before/after heating suggesting thermally-induced intramolecular doping polythiophene by the formed sulfonic acid at the side chain. The related doping was also observed in a poly(phenylacetylene) derivative, which was synthesized by rhodium-catalyzed polymerization. Copolymerization of such thiophene and acetylene bearing neopentyl sulfonate with 3-alkylthiophene and phenylacetylene produced the corresponding statistical copolymers, respectively, demonstrating the formal self-doping of poly(3-alkylthiophene) and poly(phenylacetylene).

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Section: Synthesis and Characterization Of A Polyacetylene Derivativementioning

confidence: 79%

“…The obtained copolymers were then subjected to measurements of optoelectronic properties as a thin film on quartz or the ITO electrode . As shown in Figure , the value of λ max the as-deposited film of 12 ( m = 3.7; n = 1) was 520 nm, while the film was transparent at the NIR region (>700 nm).…”

Section: Results and Discussionmentioning

confidence: 99%

Thermally Induced Self-Doping of π-Conjugated Polymers Bearing a Pendant Neopentyl Sulfonate Group

et al. 2020

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“…A thiophene derivative bearing a cyclic siloxane moiety at the side chain 29 was also found to be subjected to the polymerization to give the corresponding polymer 30 in excellent yield to confirm the solubility in hexanes in a similar manner . Thin film of the obtained polythiophene 30 was found to induce ring opening of the cyclic siloxane upon treatment with an acid vapor at 70 °C for 30 min, by which the polymer forms the siloxane gel 31 to result in being insoluble in any of organic solvents.…”

Section: Polythiophenes Of Designed Thiophene Ring and Side Chainmentioning

confidence: 90%

Dehalogenative or Deprotonative? The Preparation Pathway to the Organometallic Monomer for Transition‐Metal‐Catalyzed Catalyst‐Transfer‐Type Polymerization of Thiophene Derivatives

Shibuya

Mori

2020

Chemistry A European J

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Due to a wide range of applications in electronic materials, polythiophenes attract considerable attention in organic and polymer syntheses as well as in materials science. For the purpose of developing the practical synthetic protocol, this review focuses on the deprotonative pathway in the preparation of thiophene organometallic monomer, which was shown to be effective employing 2‐halo‐3‐substituted thiophene as a monomer precursor. The thus metallated thiophene monomer was shown to undergo polymerization by nickel(II) complex catalysis, with which highly regioregular head‐to‐tail (HT)‐type polythiophenes were obtained with controlled molecular weight and molecular weight distribution. Several polythiophene derivatives with modified thiophene‐ring and side‐chain structures were shown to be designed in order to achieve the designed functionality as materials.

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“…An additional feature of the deprotonative protocol for polythiophene is the possibility to use chlorothiophene 3, in which the use of a nickel N-heterocyclic carbene (NHC) complex was found to be effective [10,11]. We have also engaged in the design of the side chain of polythiophenes, and several functionalities have been successfully introduced [12][13][14]. We further focused on the copolymerization of thiophene, employing differently substituted thiophene monomers, with which several copolymerizations are plausible, giving thiophene-thiophene copolymers of random (statistical) [15], gradient [16,17], block [18,19], alternating [20][21][22][23], etc.…”

Section: Introductionmentioning

confidence: 99%

Formal preparation of regioregular and alternating thiophene–thiophene copolymers bearing different substituents

Mori

Fujita

Kubota

et al. 2020

Beilstein J. Org. Chem.

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Differently substituted thiophene–thiophene-alternating copolymers were formally synthesized employing a halo-bithiophene as a monomer. Nickel-catalyzed polymerization of bithiophene with substituents at the 3-position, including alkyl-, fluoroalkyl-, or oligosiloxane-containing groups, afforded the corresponding copolymers in good to excellent yield. The solubility test in organic solvents was performed to reveal that several copolymers showed a superior solubility. X-ray diffraction analysis of the thin film of the alternating copolymers composed of methyl and branched oligosiloxane substituents was also performed, and the results suggested the formation of a dual-layered film structure.

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Synthesis and Properties of Regioregular Polythiophene Bearing Cyclic Siloxane Moiety at the Side Chain and the Formation of Polysiloxane Gel by Acid Treatment of the Thin Film

Cited by 13 publications

References 53 publications

Thermally Induced Self-Doping of π-Conjugated Polymers Bearing a Pendant Neopentyl Sulfonate Group

Thermally Induced Self-Doping of π-Conjugated Polymers Bearing a Pendant Neopentyl Sulfonate Group

Dehalogenative or Deprotonative? The Preparation Pathway to the Organometallic Monomer for Transition‐Metal‐Catalyzed Catalyst‐Transfer‐Type Polymerization of Thiophene Derivatives

Formal preparation of regioregular and alternating thiophene–thiophene copolymers bearing different substituents

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