Synthesis of Poly(3-hexylthiophene), Poly(3-hexylselenophene), and Poly(3-hexylselenophene-alt-3-hexylthiophene) by Direct C–H Arylation Polymerization via N-Heterocyclic Carbene Palladium Catalysts
作者： Yu-Ying Lai , Tsu-Chien Tung , Wei-Wei Liang , Yen-Ju Cheng
DOI: 10.1021/ACS.MACROMOL.5B00488
关键词: Palladium 、 Tris 、 Organic chemistry 、 Carbene 、 Polymer chemistry 、 Thermal stability 、 Polymerization 、 Phosphine 、 Catalysis 、 Ligand 、 Chemistry
摘要: Direct C–H arylation polymerization of 2-bromo-3-hexylselenophene and 2-bromo-3-hexylthiophene catalyzed by N-heterocyclic carbene (NHC) palladium-based Pd(OAc)2-based systems has been carried out investigated. Under the optimized conditions, high molecular weight poly(3-hexylthiohphene) (P3HT) (Mn = 26.9K g/mol) with head-to-tail regioregularity (94%) can be obtained using [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloro[3-phenylallyl]palladium(II) (Pd-IPr) as catalyst. Pd-IPr exhibits a wide range working temperatures from 70 to 140 °C good catalytic reproducibility result its thermal stability. It was found that presence additional phosphine ligand, such tris(o-methoxyphenyl)phosphine, increase efficiency in Pd(OAc)2 system. This improvement is linked stability enhancement for active species during course catalysis. For first time, poly(3-hexylselenophene) (P3HS) also direct-arylat...
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