Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene: An Efficient Approach to Head-to-Tail Poly(3-hexylthiophene)

Abstract

Dehydrohalogenative polycondensation of 2-bromo-3-hexylthiophene was successful with Herrmann's catalyst and tris(2-dimethylaminophenyl)phosphine as catalyst precursors, giving head-to-tail poly(3-hexylthiophene) (HT-P3HT) with high molecular weight (M(n) = 30,600, M(w)/M(n) = 1.60) and high regioregularity (98%) in almost quantitative yield (99%).

Electroactive and Photoactive Poly[Isoindigo-alt-EDOT] Synthesized Using Direct (Hetero)Arylation Polymerization in Batch and in Continuous Flow

“…22,23 Direct (hetero)-arylation polymerization (DHAP) has also shown great potential to synthesize conjugated copolymers with high yield and molecular weight. 13,24,25 Some examples even demonstrated improved molecular weights when compared with traditional synthetic methods, 24−28 and, as was previously highlighted, 29−33 high molecular weights are essential to highperformance materials.…”

Synthesis of Soluble Polythiophene Partially Containing 3,4-Ethylenedioxythiophene and 3-Hexylthiophene by Polycondensation

“…In our case, the use of PtBu 2 Me•HBF 4 (entry 4) did not improve the molecular weight of polyHE5T compared with the case of PCy 3 •HBF 4 (entry 2). Herrmann's catalyst is also known as an effective catalyst for direct C-H coupling [37]- [39], but polycondensation did not proceed in the current system (entry 5). Very recently, Ozawa et al reported that the palladium complex with dibenzylideneacetone and P(o-MeOPh) 3 , in conjunction with pivalic acid and Cs 2 CO 3 exhibit high catalyst performance in polycondensation [40] [41].…”

Crystal structure of 4-nitro-thiophene-2-carboxylic acid, a structure with a Z′ = 4, C5H3NO4S

“…Thiophenes and related derivatives have long been of interest for use in next generation electronic materials owing to their ease of production, low cost, and synthetic versatility [1][2][3].…”