title: A unique quinolineboronic acid-based supramolecular structure that relies on double intermolecular B-N bonds for self-assembly in solid state and in solution.
abstract: 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.
authors.affiliation: Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30302-4089.
authors.forename: Yanling
authors.initials: Y
authors.lastname: Zhang
authors.forename: Minyong
authors.initials: M
authors.lastname: Li
authors.forename: Sekar
authors.initials: S
authors.lastname: Chandrasekaran
authors.forename: Xingming
authors.initials: X
authors.lastname: Gao
authors.forename: Xikui
authors.initials: X
authors.lastname: Fang
authors.forename: Hsiau-Wei
authors.initials: HW
authors.lastname: Lee
authors.forename: Kenneth
authors.initials: K
authors.lastname: Hardcastle
authors.forename: Jenny
authors.initials: J
authors.lastname: Yang
authors.forename: Binghe
authors.initials: B
authors.lastname: Wang