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Synthesis of Thiophene- and Bithiophene-Based Alternating Copolymers via Pd-Catalyzed Direct C–H Arylation

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† Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8573, Japan
‡ Nagoya Municipal Industrial Research Institute, 3-4-41, Rokuban, Atsuta-ku, Nagoya 456-0058, Japan
*E-mail: [email protected]
Cite this: ACS Macro Lett. 2012, 1, 1, 67–70
Publication Date (Web):November 15, 2011
https://doi.org/10.1021/mz200067s
Copyright © 2011 American Chemical Society
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Abstract

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Polycondensation via direct C–H arylation of thiophene derivatives gave thiophene- and bithiophene-based alternating copolymers in good yields. The optimization of the reaction conditions was investigated in terms of a catalytic system and reaction time. Under optimized conditions, the polycondensation reaction of 3,3′,4,4′-tetramethylbithiophene with 2,7-dibromo-9,9-dioctylfluorene gave poly[2,7-(9,9-dioctylfluorene)-alt-5,5′-(3,3′,4,4′-tetramethyl-2,2′-bithiophene)] with a molecular weight of 31 800 in 91% yield. The polycondensation reaction proceeded with 2 mol % of Pd(OAc)2 without the addition of a phosphine ligand in a short reaction time (3 h). Six kinds of π-conjugated polymers were synthesized by the polycondensation reaction without the use of bifunctional organometallic reagents as monomers.

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