Chemical sensing of polyols with shapeshifting boronic acids as a self-contained sensor array

Abstract

Boronic acid-substituted shapeshifting bullvalenes bearing a (13)C label are employed as sensor arrays for polyhydroxylated compounds, such as carbohydrates, flavanols, and sialic acids. The dynamic nature of the bullvalene core allows for covalent binding to a wide variety of analytes, allowing for specific analyte detection by a single NMR measurement. The resulting (13)C NMR patterns permit an inference to the identity of a particular analyte bound. Conversion of the (13)C NMR to an easy-to-read barcode provides a convenient method to catalog polyol analytes. The synthesis and study of a structurally related static sensor, which is not suitable for analyte recognition, underscores the advantages of the shapeshifting nature of the sensor.