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Synthesis of End‐capped Regioregular Poly(3‐hexylthiophene)s via Direct Arylation
Author(s) -
Wang Qifeng,
Wakioka Masayuki,
Ozawa Fumiyuki
Publication year - 2012
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201200076
Subject(s) - monomer , condensation polymer , aryl , polymer chemistry , polymerization , polymer , selectivity , materials science , catalysis , chemistry , organic chemistry , alkyl
The synthesis of regioregular head‐to‐tail poly(3‐hexylthiophene)s capped with aryl groups (Ar‐HT‐P3HTs) has been accomplished by palladium‐catalyzed polycondensation of 2‐bromo‐3‐hexylthiophene ( 1 ) via direct arylation. A variety of aryl groups are installed at the initiated end in 86%–98% selectivity using aryl bromides and iodides as capping agents. The polymerization proceeds via a two‐stage process. Before monomer 1 is consumed, the competitive formation of end‐capped and non‐capped HT‐P3HTs is operative, where the molecular weight increases linearly with monomer conversion. After 1 is consumed, the resulting polymers are coupled with each other to afford highly end‐capped HT‐P3HTs.