Chiral Fluorescence Recognition by Anthracene Fluorescent Dyes ⊂ Water-Soluble Pillar[5]arene Containing Phosphonic Acid Group (PWP[5])

Abstract

Chirality plays a pivotal role in drugs, agrochmeicals and food additives et al. The enantiomers of a chiral molecule often show huge difference in bioactivity, metabolism, and toxicity et al. thereby, the recognition of chiral molecules shows an increasingly important priority, and has become an important focus and frontier in medicine, biochemistry and other fields. In this paper, a novel method for chiral fluorescence recognition based on anthracene fluorescent dyes(AD) ⊂ water-soluble pillar[5] arene containing phosphonic acid group(PWP[5]) is developed. The AD as guest molecule can complex with PWP[5] to form 1:1 AD ⊂ PWP[5] assembly, and this assembly can be further used as a fluorescent probe to identify D/L-phenylalanine and D/L-phenylalaninol by fluorescent titration. The fluorescence intensity of the assembly was significantly reduced for D-phenylalanine and D-phenylalaninol, while L-phenylalanine or L-phenylalaninol was added to AD ⊂ PWP[5] assembly, the fluorescence intensity of the assembly almost unchanged. Hence, the chiral recognition based on assembly between the achiral fused ring fluorescent dye and achiral PWP[5] was developed.