有机化学 ›› 2012, Vol. 32 ›› Issue (06): 1093-1100.DOI: 10.6023/cjoc1109211 上一篇    下一篇

研究论文

八元瓜环对1,ω-二(2-氨基吡啶)烷烃光致环加成反应的超分子催化性能的研究

丛航a, 王杞生a, 张建新a,b, 陶朱a, 薛赛凤a   

  1. a 贵州大学应用化学研究所 贵阳 550002;
    b 贵州省天然产物重点实验室 贵阳 550003
  • 收稿日期:2011-09-21 修回日期:2012-01-11 发布日期:2012-02-22
  • 通讯作者: 张建新 E-mail:ecnuc@163.com
  • 基金资助:
    国家自然科学基金(No. 21162003)、贵州省科学技术基金(Nos. 黔科合J 字[2008]75, [2009]2073 及[2010]2126 号)资助项目.

Supramolecular Catalysis of Cucurbit[8]uril on Photocycloaddition of 1,ω-Bi(2-aminopyridinium)alkylates

Cong Hanga, Wang Qishenga, Zhang Jianxina,b, Tao Zhua, Xue Saifenga   

  1. a Institute of Applied Chemistry, Guizhou University, Guiyang 550002;
    b Key Laboratory of Chemistry for Natural Products of Guizhou Province, Guiyang 550003
  • Received:2011-09-21 Revised:2012-01-11 Published:2012-02-22
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21162003), the Natural Science Foundation of Guizhou Province (Nos. [2008]75, [2009]2073, [2010]2126).

合成了三种不同链长的1,ω-二(2-氨基吡啶)烷烃, 分别为二溴化1,4-二(2-氨基吡啶)丁烷(C4)、二溴化1,6-二(2-氨基吡啶)己烷(C6)、二溴化1,8-二(2-氨基吡啶)辛烷(C8). 考察了八元瓜环(Q[8])与上述三种1,ω-二取代烷烃的主客体相互作用, 运用1H NMR 及UV-vis 证明三种客体与Q[8]的作用模式均不相同. 在此基础上, 考察了八元瓜环对三种底物光致环加成反应的超分子催化性能. 结果表明, 由于三种底物与Q[8]的主客体作用模式不同, 八元瓜环对它们光二聚反应的超分子催化性能也各有差异.

关键词: 1,ω-二(2-氨基吡啶)烷烃, 瓜环, 光环加成反应, 主客体相互作用, 超分子催化

Three kinds of 1,ω-bi(2-aminopyridinium)alkylates, which are the 1,4-bi(2-aminopyridinium)butane dibromide (C4), 1,6-bi(2-aminopyridinium)hexane dibromide (C6) and 1,8-bi(2-aminopyridinium)octane dibromide (C8), have been synthesized, respectively. The host-guest interactions of cucurbit[8]uril (Q[8]) with the above compounds have been investigated using 1H NMR and UV-vis spectra, and the results showed that there were different interaction models in the three host-guest systems. Subsequently, the photocycloaddition reactions of the substrates have been carried out in the presence of Q[8], and the dependence of the supramolecular catalytic active on the construction of substrate was observed.

Key words: 1,ω-bi(2-aminopyridinium)alkylates, cucurbituril, photocycloaddition, host-guest interaction, supramolecular catalysis