ABSTRACT
[structure: see text] An X-ray crystallographic study of unique hydrogen-bonded supramolecular solid-state networks comprised of a tetraarylboronic acid resorcinarene is described. When 1 is recrystallized from 9:1 MeOH:EtOH, partial esterification takes place to give compound 2, the corresponding half methyl ester, which forms an infinite two-dimensional array. Each molecule participates in 12 hydrogen bonds with other macrocycles. These hydrogen bonds are both B-OH- - - OH (phenolic) and OH (phenolic)- - -OH (phenolic).
Subject(s)
Boronic Acids/chemistry , Resorcinols/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Indicators and Reagents , Models, Molecular , Molecular ConformationABSTRACT
Solutions of compound 1 exhibit dramatic, characteristic color changes in response to sugar analytes. Structurally related saccharides including glucose phosphates and amino and carboxylic acid sugars can be readily distinguished by visual inspection. These findings should promote the design of unique color sensory materials based on readily available, functional macrocyclic hosts.
