期刊
POLYMER CHEMISTRY
卷 12, 期 11, 页码 1707-1719出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1py00067e
关键词
-
资金
- National Science Center [NN204 518539, 2017/01/X/ST5/01991]
This study reported the first synthesis of new chiral polythiophenes and the successful application of chemical oxidative polymerization methods to obtain polymeric materials with optical activity and regioirregular coupling.
The first synthesis of new, chiral polythiophenes functionalized at the 3-position of the thiophene ring with a pendant containing a stereogenic sulfur atom of sulfoxides, sulfoximines or sulfinates was developed. Chemical oxidative polymerization with FeCl3 or Fe(ClO4)(3) was successfully applied for their synthesis. It has been found that FeCl3-induced polymerization of monomers functionalized with an optically active sulfoxide substituent (according to the Sugimoto procedure), leading to regioirregular, alpha-alpha ' couplings in the polythiophene backbone, yields polymeric materials with a racemized pendant. On the other hand, those polymers in which the stereogenic sulfur atom located in the sulfoxide moiety remains optically active were obtained using Fe(ClO4)(3) as a suitable substitute for FeCl3. In addition, FeCl3-induced polymerization of monomers functionalized with an optically active sulfoximine substituent gave regiorandom polythiophenes without the racemized stereogenic sulfur centre of a pendant. The structures of the isolated polymeric materials were characterized by various spectroscopic techniques (NMR, IR, UV-vis and fluorescence), and their optical activity was confirmed by polarimetric measurements and CD analysis. Incorporation of a long hydrocarbon side chain to enhance the solubility of the polymers was verified, and the results on this topic were also discussed.
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