期刊
MACROMOLECULES
卷 41, 期 19, 页码 7063-7070出版社
AMER CHEMICAL SOC
DOI: 10.1021/ma801630n
关键词
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资金
- NSF [CHE-0514031]
- MRSEC Program [DMR-0520415]
- UC Regents
- DOD
- Netherlands Organization for Scientific Research (NWO)
- Agence Nationale de la Recherche [ANR-07-JCJC-0020-01]
- Agence Nationale de la Recherche (ANR) [ANR-07-JCJC-0020] Funding Source: Agence Nationale de la Recherche (ANR)
A series of alkene-functional polymers were synthesized by controlled polymerization techniques in order to investigate and compare the efficiency and orthogonality of both photochemically and thermally initiated thiol-ene click coupling reactions. The copolymers were designed to have single or multiple alkene-functional groups along the backbone, and to evaluate the robustness of these procedures, functionalization reactions with a library of mercaptans were studied. In comparing the photoinitiated reaction to its thermal counterpart, the thiol-ene photocoupling was found to proceed with higher efficiency, require shorter reaction times for complete conversion, and displayed a higher tolerance to various backbones and functional groups. To examine the orthogonality of the thiol-ene click reaction, an asymmetric telechelic polymer based on PS was designed with alkene functionality at one end and an azide at the other. The thermally initiated thiol-ene coupling was found to be completely orthogonal with the traditional azide/alkyne click reaction allowing the individual chain ends to be quantitatively functionalized without the need for protection/deprotection strategies. From these studies, the demonstrated efficiency and orthogonality of thiol-ene chemistry shows it to be a practical addition to the family of click reactions that are suitable for polymer functionalization.
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