双-2-萘甲酸烷基酯的分子内类立方烷光二聚体的手性拆分

doi:10.7517/j.issn.1674-0475.2012.05.321

影像科学与光化学 ›› 2012, Vol. ›› Issue (5): 321-329.DOI: 10.7517/j.issn.1674-0475.2012.05.321

• 研究快讯 • 下一篇

双-2-萘甲酸烷基酯的分子内类立方烷光二聚体的手性拆分

程素芳^1,2, 陈彬¹, 张丽萍¹, 佟振合¹, 吴骊珠¹

1. 中国科学院理化技术研究所光化学转换与功能材料重点实验室, 北京 100190;
2. 中国科学院研究生院, 北京 100049

收稿日期:2012-04-27 修回日期:2012-06-27 出版日期:2012-09-15 发布日期:2012-05-25
通讯作者: 吴骊珠,E-mail:lzwu@mail.ipc.ac.cn;陈彬,E-mail:chenbin@mail.ipc.ac.cn.
基金资助:
科技部国家重点基础研究发展规划项目(2010CB833304, 2007CB808004);国家自然科学基金资助项目(20920102033, 20972171, 91027041).

Chiral Resolution of Intramolecular Cubane-Like Photodimers from Alkyl bis-2-Naphthoates

CHENG Su-fang^1,2, CHEN Bin¹, ZHANG Li-ping¹, TONG Zhen-he(TUNG Chen-ho)¹, WU Li-zhu¹

1. Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China;
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received:2012-04-27 Revised:2012-06-27 Online:2012-09-15 Published:2012-05-25

摘要/Abstract

摘要： 双-2-萘甲酸多亚甲基二醇酯(N-M_n-N,n=2,3,4,5)在环己烷中进行光二聚反应的效率和产物的结构明显受链节长度的影响.N-M₃-N生成反式-头头和顺式-头头两种结构的类立方烷,而N-M₄-N和N-M₅-N高产率、高区域选择性地生成反式-头头结构的类立方烷.更有意义的是,我们利用高效液相色谱成功拆分了反式-头头结构的分子内光二聚产物.

关键词: 双-2-萘甲酸多亚甲基二醇酯, 分子内光二聚反应, 类立方烷化合物, 区域选择性, 手性拆分

Abstract: The photodimerization of polymethylene bis-2-naphthoates (N-M_n-N, n=2, 3, 4, 5) is very dependent on the length of alkyl chain in cyclohexane. Under light irradiation, N-M₃-N gave both anti-head-to-head and syn-head-to-head photodimers, while N-M₄-N and N-M₅-N each exclusively produced anti-head-to-head photodimer with high yield and high regioselectivity. Importantly, the intramolecular anti-head-to-head cubane-like photodimer has been successfully resolved into its enantiomers by HPLC.

Key words: polymethylene bis-2-naphthoates, intramolecular photodimerization, cubane-like photodimers, regioselectivity, chiral resolution

中图分类号:

程素芳, 陈彬, 张丽萍, 佟振合, 吴骊珠. 双-2-萘甲酸烷基酯的分子内类立方烷光二聚体的手性拆分[J]. 影像科学与光化学, 2012, (5): 321-329.

CHENG Su-fang, CHEN Bin, ZHANG Li-ping, TONG Zhen-he(TUNG Chen-ho), WU Li-zhu. Chiral Resolution of Intramolecular Cubane-Like Photodimers from Alkyl bis-2-Naphthoates[J]. Imaging Science and Photochemistry, 2012, (5): 321-329.

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双-2-萘甲酸烷基酯的分子内类立方烷光二聚体的手性拆分

Chiral Resolution of Intramolecular Cubane-Like Photodimers from Alkyl bis-2-Naphthoates

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