A unique quinolineboronic acid-based supramolecular structure that relies on double intermolecular B–N bonds for self-assembly in solid state and in solution

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-asse...

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Bibliographic Details
Published in:Tetrahedron 2007-04, Vol.63 (16), p.3287-3292
Main Authors: Zhang, Yanling, Li, Minyong, Chandrasekaran, Sekar, Gao, Xingming, Fang, Xikui, Lee, Hsiau-Wei, Hardcastle, Kenneth, Yang, Jenny, Wang, Binghe
Format: Article
Language:English
Subjects:
Crystal structure
NMR
Quinolineboronic acid
Self-assembly
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Summary: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, π–π 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.02.042