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Extremely regio‐regular poly (3‐alkylthiophene)s from simplified chain‐growth Grignard metathesis polymerisations and the modification of their chain‐ends
Author(s) -
Hiorns Roger C,
Khoukh Abdel,
Gourdet Benoit,
DagronLartigau Christine
Publication year - 2006
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.2013
Subject(s) - polymer chemistry , metathesis , formylation , chain (unit) , polymer , polymerization , side chain , copolymer , materials science , chemistry , solubility , polymer science , organic chemistry , catalysis , physics , astronomy
Abstract A simplified route to regio‐regular poly(3‐alkylthiophene)s (P3AT) with predetermined molecular weights and low molecular weight distributions based on the chain‐growth GRIM polymerisation of 2,5‐dibromo‐3‐alkylthiophenes is detailed. It is proposed by way of in‐depth 13 C‐, 1 H‐ and two‐dimensional NMR characterisations that the resulting P3ATs are quasi ‐100% regio‐regular except for one regio‐irregular pair at one chain‐end. It is probable that chain‐end groups exhibit reduced conjugation with the rest of the polymer. A comparison of the preparation of poly(3‐hexylthiophene) and poly(3‐butylthiophene) (P3BT) is presented. New methods required for the hydrogenation, formylation and bromomethylation of the chain‐ends of P3BT, necessary to overcome its poor solubility and low reactivity, are described. Copyright © 2006 Society of Chemical Industry