Optical and Fluorescent Dual Sensing of Aminoalcohols by in Situ Generation of BODIPY-like Chromophore

J Am Chem Soc. 2020 Mar 18;142(11):4975-4979. doi: 10.1021/jacs.9b13232. Epub 2020 Mar 5.

Abstract

A novel multifunctional aminophenylboronic acid connected to a diphenylketone gives both circular dichroism and fluorescence signals by in situ generation of a BODIPY-like chromophore in the presence of aminoalcohols. DFT calculations were used to understand the role of each functional group in the mechanism. This new sensor can distinguish different aminoalcohols and quantitatively indicate the concentration of the substrate, allowing for the convenient determination of the ee of racemic mixtures with a single probe.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / analysis*
  • Benzophenones / chemistry*
  • Boron Compounds / chemistry*
  • Circular Dichroism
  • Density Functional Theory
  • Fluorescent Dyes / chemistry*
  • Models, Chemical

Substances

  • Amino Alcohols
  • Benzophenones
  • Boron Compounds
  • Fluorescent Dyes