Synthesis and properties of poly(3,4-dimethoxythiophene)

Hagiwara, Toru; Yamaura, M.; Sato, Kyosuke; Hirasaka, Masao; Iwata, Kaoru

doi:10.1016/0379-6779(89)90778-9

Cited by 42 publications

(13 citation statements)

References 27 publications

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“…Comparable results have been published by Hagiwara et al [90] for the thermal dedoping of Cl04 doped poly (3,4-dimethoxythiophene). Although the given data do not allow an accurate interpretation in terms of an activation energy, an estimate EA < 10000 K can be made.…”

Section: Deoopingsupporting

confidence: 80%

Processable Conducting Poly(3-Alkylthiopenes)

Gustafsson

Inganäs

Salaneck

et al. 1991

Conjugated Polymers

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ABSTRACf. The poly(3-alkylthiophenes) represent a new generation of conducting polymers, that exhibit both solution and melt processability. These properties open new possibilities for the utilization of conducting polymers in practical applications. Furtheonore, the solubility of these polymers enables the characterization of the physical and chemical structure in greater detail than hitherto have been possible. In this chapter we give a brief review of the synthetic routes to the poly(3-alkylthiophenes) as well as an overview of some of the recent results on the physical and chemical characterization of this class of materials. In this overview we include results on stability properties, transport properties, thermo-and solvatochromism. We also discuss some aspects of the utilization of the poly(3-alkylthiophenes) in applications.

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Section: Deoopingsupporting

confidence: 80%

Processable Conducting Poly(3-Alkylthiopenes)

Gustafsson

Inganäs

Salaneck

et al. 1991

Conjugated Polymers

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“…Introducing a flexible side chain such as an alkyl group with carbon number four or more on the 3-position of the thiophene ring allows the polymer to become soluble in common organic solvents, fusible, and melt processable while retaining a rather high conductivity, about 30-100 S/cm, after doping.2-4 In order to control optical, electrical, and electrochemical properties of poly(3-alkylthiophene)s (P3 AT), introduction of various numbers of oxygen atoms at various positions in the side chain has been attempted. [5][6][7][8][9][10][11][12] Incorporation of an alkoxy group with carbon number varying from 1 to 15 on the 3-position of the thiophene ring gives polymers with an optical absorption maximum at 475-530 nm comparable with those of P3ATs but with a lower conductivity of about KH-10-2 S/cm after electrochemical doping due to lower molecular weight (MW) and with a lower oxidation potential due to electrondonating characteristics of the oxygen. [6][7][8] The polymers are soluble in organic solvents even after doping up to 20 %.…”

Section: Introductionmentioning

confidence: 99%

Structure/properties of conjugated conductive polymers. 2. 3-Ether-substituted polythiophenes and poly(4-methylthiophenes)

Chen¹,

Tsai²

1993

Macromolecules

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Two series of 3-substituted polythiophenes (PTs) and poly(4-methylthiophene)~ (P4MTs) having the Substituents containing 8 atoms in the backbone with oxygen as the first atom bonded to the thiophene ring, C,H&-, C~HBOC~H~O-, and CH30C2H~OC2H~O-for the former series and having the first two substituents for the latter series were synthesized by chemical polymerization using ferric chloride as the oxidizing agent and characterized using thermal analysis, various spectroscopic methods, cyclic voltammetry, and conductivity measurement. For the first series, in comparison with poly(3-octylthiophene) (P30T; A, , = 480 nm), a replacement of the first carbon attached to the thiophene ring by an oxygen atom leads to a decreased band gap ( A, = 580 nm) due to the electron-donating nature of the oxygen. Further substitution on the 4-position of the thiophene ring with the methyl group of the 3-substituted PT with the substituent C,H&-leads to an increase in the band gap due to a decrease in conjugation caused by a steric hindrance of the methyl group as reflected in the change of A, , from 580 to 420 nm. But ita oxidation potential (0.76 V) ia lower than that of P30T (1.01 V) due to electron donation to the ?r system by the oxygen. Additional replacement of the third carbon atom by an oxygen atom in the side chain (giving CdHsOC2H40-) improves the conjugation (as reflected by an increase in A, , to 530 nm and a decrease in the oxidation potential to 0.6 V) due to a strong interaction between neighboring side chains, such that no thermochromism is observed before a decomposition of side chains.

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“…The stretching vibrations of C=C in thiophene ring are observed at 1390 and 1471 cm -1 , while the bands at 1226 and 1349 cm -1 originate from C-C bonds (Lattach et al, 2014;Kvarnström et al, 1999;Ghosh et al, 2014). Remarkably, the ATR-FTIR spectrum of EDOT displays typical bands at 755 cm -1 , attributed to the =C-H in-plane and out-of-plane deformation vibrations, which are not detected in the infrared spectrum of PEDOT (Hagiwara et al, 1989). The disappearance of these bands upon irradiation highlights the involvement of α,α'-coupling reactions during PEDOT growth (Lattach et al, 2013;Lattach et al, 2014;Akimoto et al, 1986) (see Scheme 1), confirming that the dose of 72 kGy used during irradiation leads, as expected, to quantitative polymerization of EDOT.…”

Section: Chemical and Structural Characterizations Of Pedot Polymers ...mentioning

confidence: 89%