Facile, efficient routes to diverse protected thiols and to their deprotection and addition to create functional polymers by thiol-ene coupling

被引:101
作者
David, R. L. Ameri [1 ]
Kornfield, Julia A. [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
D O I
10.1021/ma0718393
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Carbazole, dinitrobenzoate, phenol, pyridine, and 4-cyano-4 '-alkoxybiphenyl side groups were grafted onto pendant vinyl groups of polybutadiene (PB) by thiol-ene addition to yield functional polymer of polydispersity equal to that of the precursor material. Synthesis protocols that are clean (> 90% conversion to desired product) and scalable were developed to incorporate a protected thiol group into functional precursors. The resulting acetyl or benzoyl thioesters are suitable for long-term storage, and are conveniently deprotected and added to polymer in a matter of hours in a straightforward procedure that does not require isolation of the thiol intermediate. Alternatively, PB functionalization could be achieved with equal success by reaction with P-mercaptoethanol (BME), and subsequent esterification of the incorporated hydroxyl groups with a suitable acyl halide. The chemistry described can potentially be applied to add any side group onto any polymer, copolymer, or block copolymer displaying pendant vinyl groups.
引用
收藏
页码:1151 / 1161
页数:11
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