Enantioselective Fluorescent Sensors for Chiral Alpha-Hydroxycarboxylic Acids, Amino Acid derivatives and Diamines

Abstract

A series of enantioselective fluorescent sensors based on chiral 1,1'-bi-2-naphathol (BINOL) was designed and developed for the recognition of chiral α-hydroxycarboxylic acids, amino acid derivatives and diamines.A new concept with the use of a pseudoenantiomeric fluorescent sensor pair for A BINOL-amino alcohol enantiomeric pair is discovered to be able to conduct both enantioselective and diastereoselective fluorescent discrimination of the four stereoisomers of threonine derivatives. This is the first example that one enantiomeric sensor pair can be used to recognize four stereoisomers of chiral substrates containing iii two chiral centers.A BINOL-trifluoroacetyl compound is discovered to exhibit high sensitivity at one emission wavelength and high enantioselectivity at another when treated with a chiral diamine. By using this fluorescent sensor it was demonstrated for the first time that both the concentration and enantiomeric composition of a chiral substrate can be determined simultaneously with one fluorescent measurement.These discoveries represent important progress in the field of enantioselective fluorescent sensors and have fundamental significance for the potential application of fluorescence in chiral catalyst screening.