Facile syntheses of dioxythiophene-based conjugated polymers by direct C-H arylation

Haichao Zhao; Ching Yuan Liu; Shyh Chyang Luo; Bo Zhu; Tsai Hui Wang; Hsiu Fu Hsu; Hsiao Hua Yu

doi:10.1021/ma300719n

Facile syntheses of dioxythiophene-based conjugated polymers by direct C-H arylation

Haichao Zhao, Ching Yuan Liu, Shyh Chyang Luo, Bo Zhu, Tsai Hui Wang, Hsiu Fu Hsu, Hsiao Hua Yu

Department of Chemical and Materials Engineering

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

Abstract

Various substituted dioxythiophenes bearing 3,4-propylenedioxythiophenes (ProDOT) and 3,4-ethylenedioxythiophene (EDOT) moieties successfully undergo Pd-catalyzed direct C-H arylation to yield π-conjugated polymers. The effects of palladium catalysts, phosphine ligands or additives, and functional groups on this facile polycondensation approach are investigated. Polymers from alkoxy-substituted ProDOT are synthesized with reasonable molecular weight (M _n = 6100-9600) and low PDI (1.3-1.9). Four substituted EDOT with alkoxy or protected functional groups also undergo direct C-H arylation polycondensation to yield corresponding polymers. The obtained polydioxythiophenes exhibit UV-vis absorptions ranging from 480 to 590 nm, and these conjugated polymers are electroactive and reversibly switched between the oxidized and neutral states upon applying potentials.

Original language	English
Pages (from-to)	7783-7790
Number of pages	8
Journal	Macromolecules
Volume	45
Issue number	19
DOIs	https://doi.org/10.1021/ma300719n
State	Published - 9 Oct 2012

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abstract = "Various substituted dioxythiophenes bearing 3,4-propylenedioxythiophenes (ProDOT) and 3,4-ethylenedioxythiophene (EDOT) moieties successfully undergo Pd-catalyzed direct C-H arylation to yield π-conjugated polymers. The effects of palladium catalysts, phosphine ligands or additives, and functional groups on this facile polycondensation approach are investigated. Polymers from alkoxy-substituted ProDOT are synthesized with reasonable molecular weight (M n = 6100-9600) and low PDI (1.3-1.9). Four substituted EDOT with alkoxy or protected functional groups also undergo direct C-H arylation polycondensation to yield corresponding polymers. The obtained polydioxythiophenes exhibit UV-vis absorptions ranging from 480 to 590 nm, and these conjugated polymers are electroactive and reversibly switched between the oxidized and neutral states upon applying potentials.",

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T1 - Facile syntheses of dioxythiophene-based conjugated polymers by direct C-H arylation

AU - Zhao, Haichao

AU - Liu, Ching Yuan

AU - Luo, Shyh Chyang

AU - Zhu, Bo

AU - Wang, Tsai Hui

AU - Hsu, Hsiu Fu

AU - Yu, Hsiao Hua

PY - 2012/10/9

Y1 - 2012/10/9

N2 - Various substituted dioxythiophenes bearing 3,4-propylenedioxythiophenes (ProDOT) and 3,4-ethylenedioxythiophene (EDOT) moieties successfully undergo Pd-catalyzed direct C-H arylation to yield π-conjugated polymers. The effects of palladium catalysts, phosphine ligands or additives, and functional groups on this facile polycondensation approach are investigated. Polymers from alkoxy-substituted ProDOT are synthesized with reasonable molecular weight (M n = 6100-9600) and low PDI (1.3-1.9). Four substituted EDOT with alkoxy or protected functional groups also undergo direct C-H arylation polycondensation to yield corresponding polymers. The obtained polydioxythiophenes exhibit UV-vis absorptions ranging from 480 to 590 nm, and these conjugated polymers are electroactive and reversibly switched between the oxidized and neutral states upon applying potentials.

AB - Various substituted dioxythiophenes bearing 3,4-propylenedioxythiophenes (ProDOT) and 3,4-ethylenedioxythiophene (EDOT) moieties successfully undergo Pd-catalyzed direct C-H arylation to yield π-conjugated polymers. The effects of palladium catalysts, phosphine ligands or additives, and functional groups on this facile polycondensation approach are investigated. Polymers from alkoxy-substituted ProDOT are synthesized with reasonable molecular weight (M n = 6100-9600) and low PDI (1.3-1.9). Four substituted EDOT with alkoxy or protected functional groups also undergo direct C-H arylation polycondensation to yield corresponding polymers. The obtained polydioxythiophenes exhibit UV-vis absorptions ranging from 480 to 590 nm, and these conjugated polymers are electroactive and reversibly switched between the oxidized and neutral states upon applying potentials.

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M3 - 期刊論文

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JO - Macromolecules

JF - Macromolecules

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ER -

Facile syntheses of dioxythiophene-based conjugated polymers by direct C-H arylation

Abstract

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