期刊
PURE AND APPLIED CHEMISTRY
卷 85, 期 3, 页码 573-587出版社
WALTER DE GRUYTER GMBH
DOI: 10.1351/PAC-CON-12-03-13
关键词
catalysis; catalysts; conjugated polymers; coupling reactions; Kumada; nickel; organic semiconductors; palladium catalyst-transfer; Suzuki
Catalyst-transfer condensation polymerization, in which the catalyst activates the polymer end-group, followed by reaction with the monomer and transfer of the catalyst to the elongated polymer end-group, has made it feasible to control the molecular weight, poly dispersity, and end-groups of pi-conjugated polymers. In this paper, our recent progress of Kumada-Tamao Ni catalyst-transfer coupling polymerization and Suzuki-Miyaura Pd catalyst-transfer coupling polymerization is described. In the former polymerization method, the polymerization of Grignard pyridine monomers was investigated for the synthesis of well-defined n-type pi-conjugated polymers. Para-type pyridine monomer, 3-alkoxy-2-bromo-5-chloromagnesiopyridine, afforded poly(pyridine-2,5-diyl) with low solubility in the reaction solvent, whereas meta-type pyridine monomer, 2-alkoxy-5-bromo-3-chloromagnesiopyridine, yielded soluble poly(pyridine-3,5-diyl) with controlled molecular weight and low polydispersity. In Suzuki-Miyaura catalyst-transfer coupling polymerization, t-Bu3PPd(Ph)Br was an effective catalyst, and well-defined poly(p-phenylene) and poly(3-hexylthiophene) (P3HT) were obtained by concomitant use of CsF/18-crown-6 as a base in tetrahydrofuran (THF) and a small amount of water.
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