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

doi:10.7503/cjcu20120582

Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (12): 2657.doi: 10.7503/cjcu20120582

• Organic Chemistry • Previous Articles Next Articles

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

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

Abstract

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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TrendMD:

YI Ping-Gui, YANG Xi-Chun, YU Xian-Yong, LIU Zheng-Jun, LIU Jin, WANG Zhao-Xu, LI Xiao-Fang. Proton Transfer of 2-(2-Amino-3-pyridyl)-benzimidazole Under the Inclusion Interaction with Cucurbit[8]uril[J]. Chem. J. Chinese Universities, 2012, 33(12): 2657.

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

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