TETRAHEDRON | 卷:63 |
A unique quinolineboronic acid-based supramolecular structure that relies on double intermolecular B-N bonds for self-assembly in solid state and in solution | |
Article | |
Zhang, Yanling ; Li, Minyong ; Chandrasekaran, Sekar ; Gao, Xingming ; Fang, Xikui ; Lee, Hsiau-Wei ; Hardcastle, Kenneth ; Yang, Jenny ; Wang, Binghe | |
关键词: quinolineboronic acid; self-assembly; crystal structure; NMR; | |
DOI : 10.1016/j.tet.2007.02.042 | |
来源: Elsevier | |
【 摘 要 】
The boronic acid functional group plays very important roles in sugar recognition, catalysis, organic synthesis, and supramolecular assembly. Therefore, understanding the unique properties of this functional group is very important. 8-Quinolineboronic acid (8-QBA) is found to be capable of self-assembling in solid state through a unique intermolecular B-N bond mechanism reinforced by intermolecular boronic anhydride formation, pi-pi stacking, and hydrogen bond formation. NMR NOE and diffusion studies indicate that intermolecular B-N interaction also exists in solution with 8-QBA. In contrast, a positional isomer of 8-QBA, 5-quinolineboronic acid (5-QBA) showed very different behaviors in crystal packing and in solution and therefore different supramolecular network. Understanding the structural features of this unique 8-QBA assembly could be very helpful for the future design of new sugar sensors, molecular catalysts, and supramolecular assemblies. (c) 2007 Elsevier Ltd. All rights reserved.
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