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Precision Synthesis of poly(3-hexylthiophene) From Catalyst-Transfer Suzuki-Miyaura Coupling Polymerization

Precision Synthesis of poly(3-hexylthiophene) From Catalyst-Transfer Suzuki-Miyaura Coupling Polymerization

Tsutomu Yokozawa, Ryosuke Suzuki, Masataka Nojima, Yoshihiro Ohta, Akihiro Yokoyama

Macromol Rapid Commun. 2011 Jun 1;32(11):801-6.

PMID: 21509845

Abstract:

(t)Bu(3) PPd(Ph)Br (1)-catalyzed Suzuki-Miyaura coupling polymerization of 2-(4-hexyl-5-iodo-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2) was investigated. Monomer 2 was polymerized with 1 at 0 °C in the presence of CsF and 18-crown-6 in THF containing a small amount of water to yield P3HT with a narrow molecular weight distribution and almost perfect head-to-tail regioregularity. The M(n) values increased up to 11,400 g · mol(-1) in proportion to the feed ratio of 2 to 1. The MALDI-TOF mass spectra showed that P3HT with moderate molecular weight uniformly had a phenyl group at one end and a hydrogen atom at the other, indicating involvement of a catalyst-transfer mechanism. Successive 1-catalyzed polymerization of fluorene monomer 3 and then 2 yielded a well-defined block copolymer of polyfluorene and P3HT.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS793334	2-(4-fluoro-2-methylphenyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane			Price
LS793384	2-[3-([1,3]dioxolan-2-ylmethoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane			Price

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