Functional Polythiophene Bearing Hydroxyethyl Groups and Their Derivatives

Hyun-Chul Kim; Jong-Seong Kim; Sungsik Baek; Moonhor Ree

Macromolecular Research, Vol.14, No.2, 173-178, April, 2006

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Functional Polythiophene Bearing Hydroxyethyl Groups and Their Derivatives

Hyun-Chul Kim, Jong-Seong Kim, Sungsik Baek, and Moonhor Ree^†

School of Environmental Science and Engineering, Department of Chemistry,National Research Lab for Polymer Synthesis & Physics, Polymer Research Institute,Division of Molecular and Life Sciences (BK21 Program), Pohang University of Science & Technology (Postech), Pohang 790-784, Korea

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Poly(3-(2-hydroxyethyl)thiophene) (P3HET) was synthesized using oxidative coupling polymerizationthat involved the protecting and deprotecting of hydroxyl groups but not the chlorine substitution or oxidativedecomposition of the hydroxyl groups. The resulting P3HET exhibited good solubility in aprotic solvents, in contrastto the insoluble polymer product synthesized directly from the monomer, 3-(2-hydroxyethyl)thiophene (3HET).P3HET had low conductivity due to the strong hydrogen bonding of its hydroxyl groups. The ester-functionalizedpoly(3-(2-acetoxyethyl)thiophene) and poly(3-(4-pentylbenzoateethyl)thiophene) were also prepared with reasonablyhigh molecular weights in order to examine how this functionalization modified the physical and chemical propertiesof P3HET. These polymers exhibited better solubility in common solvents and higher conductivity than P3HET. Allthese polymers exhibited bathochromic shifts of their film state absorption maxima with respect to those found inthe UV-visible spectra of their solution phases. The extent of the bathochromic shift was found to vary with thelengths of the side chains of the ester-functionalized polymers.

Keywords:3-substituted polythiophene;conjugated polymer;conductivity;bathochromic shift

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[Referenced By]

[1] MacDiarmid AG, Chiang JC, Richter AF, Somasiri NLD, Epstein AJ, in Conducting Polymers, L. Alcacer, ed., Dordrecht, Reidel, p 105 (1987)

[2] Diaz AF, Kanazawa KK, Gardini GP, J. Chem. Soc. Chem. Commun.(14), 635 (1979)

[3] Tourillon G, Gamier F, J. Electroanal. Chem., 135, 172 (1982)

[4] Zotti G, Salmaso R, Gallazzi M, Marin R, Chem. Mater., 9, 791 (1997)

[5] Zotti G, Marin R, Gallazzi M, Chem. Mater., 9, 2945 (1997)

[6] Levesque I, Leclerc M, Chem. Mater., 8, 2843 (1996)

[7] Shim HK, Ahn T, Lee HY, Lee JI, Korea Polym. J., 9(2), 116 (2001)

[8] Kim BS, Chen L, Gong JP, Osada Y, Korea Polym. J., 8(3), 116 (2000)

[9] Kim BS, Osada Y, Korea Polym. J., 7(6), 350 (1999)

[10] Park SB, Kim H, Zin WC, Jung JC, Macromolecules, 26, 1627 (1993)

[11] Thomas O, Inganas O, Andersson MR, Macromolecules, 31(8), 2676 (1998)

[12] Sato M, Tanaka S, Kaeriyama K, J. Chem. Soc. Chem. Commun., 873 (1986)

[13] Yamamoto T, Komarudin D, Arai M, Lee BL, Suganuma H, Asakawa N, Inoue Y, Kubota K, Sasaki S, Fukuda T, Matsuda H, J. Am. Chem. Soc., 120(9), 2047 (1998)

[14] Roncali J, Chem. Rev., 97(1), 173 (1997)

[15] Costa Bizzarri P, Andreani F, Della Casa C, Lanzi M, Salatelli E, Synth. Met., 75, 141 (1995)

[16] Chen SA, Kung HP, Tsai CC, Hou CN, Liao CS, Synth. Met., 55, 582 (1993)