期刊
CHEMICAL COMMUNICATIONS
卷 56, 期 54, 页码 7419-7422出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc02601h
关键词
-
资金
- National Research Foundation of Korea - Korean government (MSIP) [NRF-18R1D1A1B07048527]
- National Research Foundation of Korea [2018R1D1A1B07048527] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
The base-catalyzed oxirane ring opening reaction with thiol nucleophiles is frequently employed for post-polymerization modification of polymeric glycidyl scaffolds. Due to various beneficial attributes, it is often referred to as a 'click' reaction. However, the tendency of the free thiol molecules to undergo oxidative dimerization through the formation of a disulfide bond under ambient conditions results in partial consumption of the sulfhydryl precursors. Therefore, an excess of the thiol precursors is typically used to counterbalance the side-reaction. This violates the equimolar stoichiometry conditions required for 'click' reactions in the context of polymer synthesis. Here, we show that commercially available disulfides can be used to generate the necessary thiolate nucleophilesin situthrough the reduction of the SS-bond with sodium borohydride. Such activation strategy eliminates the sulfhydryl oxidation mechanism to disulfides and ensures that the post-synthesis functionalization of epoxy polymers can be performed under equimolar 'click' conditions.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据