Polymer-supported synthesis of regioregular head-to-tail-coupled oligo(3-arylthiophene)s utilizing a traceless silyl linker

被引:57
作者
Briehn, CA [1 ]
Kirschbaum, T [1 ]
Bäuerle, P [1 ]
机构
[1] Univ Ulm, Abt Organ Chem 2 Organ Mat & Combinatorial Chem, D-89081 Ulm, Germany
关键词
D O I
10.1021/jo991188b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-arylthiophene)s has been achieved in high yield and purity by using a traceless silyl ether linkage. In the first step, the solution-phase synthesis of this class of conjugated oligomers was investigated. Benzyl alcohol was chosen to serve as a mimic for the anchoring group of the hydroxymethyl-substituted polystyrene matrix. The development of a novel regioselective iodination process for silyl-protected thiophenes faciliates the successful application of the solution-phase protocol to the solid phase. Satisfactory loading was obtained by reaction of chlorosilyl-functionalized 3-arylthiophene with hydroxymethyl polystyrene in the presence of imidazole. The suitability of the following iterative halogenation and Suzuki cro ss-coupling sequence is illustrated by the preparation of a quater(3-arylthiophene), the first regioregular head-to-tail-coupled oligothiophene that is synthesized on solid support. Removal of the conjugated oligomers from the solid support could be effectively achieved by treatment with tetrabutylammonium fluoride.
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页码:352 / 359
页数:8
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