高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (12): 2657-2662.doi: 10.7503/cjcu20120582

• 有机化学 • 上一篇    下一篇

八元瓜环超分子作用下2-(2-氨基-3-吡啶基)苯并咪唑的质子转移

易平贵, 阳习春, 于贤勇, 刘峥军, 刘金, 汪朝旭, 李筱芳   

  1. 湖南科技大学化学化工学院, 理论化学与分子模拟省部共建教育部重点实验室, 分子构效关系湖南省普通高等学校重点实验室, 湘潭 411201
  • 收稿日期:2012-06-20 出版日期:2012-12-10 发布日期:2012-11-20
  • 通讯作者: 易平贵,男,博士,教授,博士生导师,主要从事分子构效与理论计算研究.E-mail:pgyi@hnust.cn E-mail:pgyi@hnust.cn
  • 基金资助:

    国家自然科学基金(批准号: 21172066, 20971041)、湖南省自然科学基金(批准号: 11JJ2007)和湖南省高校创新平台开放基金(批准号: 09K081)资助.

Proton Transfer of 2-(2-Amino-3-pyridyl)-benzimidazole Under the Inclusion Interaction with Cucurbit[8]uril

YI Ping-Gui, YANG Xi-Chun, YU Xian-Yong, LIU Zheng-Jun, LIU Jin, WANG Zhao-Xu, LI Xiao-Fang   

  1. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China
  • Received:2012-06-20 Online:2012-12-10 Published:2012-11-20

摘要:

利用荧光发射光谱、 紫外吸收光谱和核磁共振氢谱(1H NMR)研究了八元瓜环(CB8)与2-(2-氨基-3-吡啶基)苯并咪唑(2-A3PyBI)的超分子相互作用及其对2-A3PyBI分子内质子转移过程的影响. 结果表明, 在水溶液中2-A3PyBI具有双重荧光发射峰, 分别对应其2种质子转移异构体. 固定pH值下的荧光滴定实验表明主客体包合比为1:2, 2-A3PyBI进入CB8空腔后促进了其分子内激发态质子转移过程. 同时, 1H NMR结果表明2-A3PyBI的苯环部分进入了CB8空腔.

关键词: 2-(2-氨基-3-吡啶基)苯并咪唑, 八元瓜环, 相互作用, 超分子, 质子转移

Abstract:

The inclusion interaction of 2-(2-amino-3-pyridyl)-benzimidazole(2-A3PyBI) with cucurbit[8]uril(CB8) and the effect of the interaction on the proton transfer of 2-A3PyBI were studied via fluorescence emission spectroscopy, UV absorption spectroscopy and 1H NMR. The results show that 2-A3PyBI has a dual emission fluorescence which corresponds to its proton transfer tautomers. The fluorescence titration results at selected pH value indicate that the interaction ratio is 1:2 and the encapsulation of 2-A3PyBI into CB8 cavity enhances the excited-state intramolecular proton transfer process. The 1H NMR titration results, which the benzene ring signal upward but no obviously change of the pyridine ring was observed in DCl/D2O, indicate that the benzene ring of 2-A3PyBI entrapped into the CB8 cavity with the pyridine ring outside the cavity.

Key words: 2-(2-Amino-3-pyridyl)-benzimidazole, Cucurbit[8]uril, Interaction, Supramolecule, Proton transfer

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