Extremely regio-regular poly (3-alkylthiophene)s from simplified chain-growth Grignard metathesis polymerisations and the modification of their chain-ends

被引:37
作者
Hiorns, Roger C. [1 ]
Khoukh, Abdel [1 ]
Gourdet, Benoit [1 ]
Dagron-Lartigau, Christine [1 ]
机构
[1] CNRS, UMR 5067, Lab Phys Chim Polymeres, F-64053 Pau 9, France
关键词
chain-growth Grignard metathesis (GRIM) polymerisation; poly(3-butylthiophene); poly(3-hexylthiophene) (P3HT); chain-end modifications; formylation; bromomethylation; conjugation;
D O I
10.1002/pi.2013
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
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 C-13-, H-1- 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. (c) 2006 Society of Chemical Industry.
引用
收藏
页码:608 / 620
页数:13
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