Design, synthesis, and control of conducting polymer architectures: structurally homogeneous poly(3-alkylthiophenes)

The full details of a facile synthesis of structurally homogeneouspoly(3-alkylthiophene) (PAT's) is presented. In three steps from 3-bromothiophene, PAT's can be made with complete regiochemical control. We define structurally homogenous an a regiochemically well-defined polymer structure that in oar cane contains almsost exclusively head-to-tail couplings (HT-HT) (2,5-couplings between adjacent thiophene rings). By analysis of the NMR data, oar poly(n-butylthiophene) (5a) contains 93% HT-HT couplings, 98% of the desired regiochemistry is found in poly(n-hexylthiophene) (5b), 97% in poly(n-octylthiophene), (5c), and 95% in poly(n-dodecylthiophene), (5d)