Journal
MACROMOLECULAR RAPID COMMUNICATIONS
Volume 34, Issue 1, Pages 69-73Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/marc.201200550
Keywords
conjugated polymers; direct arylation; ethylenedioxythiophene; Pd catalyst; polycondensation
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Funding
- Collaborative Research Program of Institute for Chemical Research, Kyoto University
- New Energy and Industrial Technology Development Organization (NEDO) of Japan
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The polycondensation reaction of 3,4-ethylenedioxythiophene with 2,7-dibromo-9,9-dioctylfluorene via Pd-catalyzed direct arylation gives poly[(3,4-ethylenedioxythiophene-2,5-diyl)-(9,9-dioctylfluorene-2,7-diyl)]. The reaction conditions are optimized in terms of the Pd precatalysts, reaction time, and carboxylic acid additives. The combination of 1 mol% Pd(OAc)(2) and 1-adamantanecarboxylic acid as an additive is the optimized catalytic system, and it yields the corresponding polymer with a molecular weight of 39 400 in 89% yield. The polycondensation reaction, followed by an end-capping reaction, effectively provides a linear poly mer without Br terminals.
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