A fluorescent clever macrocycle: Deca-bodipy bearing a pillar [5]arene and its selective binding of asparagine in half-aqueous medium

Abstract

Herein, two generic classes, pillar[n]arene and Bodipy, were combined for the selective detection of basic amino acids. For this aim, a Pillar [5]arene and Bodipy derivatives were synthesized, then, a fluorescent macrocycle (P5-Bodipy) was firstly prepared by using ‘click’ chemistry. The chemical analysis of the compounds was illuminated by some techniques such as 1H NMR, FT-IR, 13C NMR, melting point, elemental analysis, and mass spectroscopy. The sensitivity of P5-Bodipy towards amino acids (Glycine, Alanine, Valine, Phenylalanine, Leucine, Asparagine, Glutamine, Tryptophan, Methionine, Tyrosine, Serine, Threonine, Arginine) was fluorometrically examined in a half-aqueous medium. The electrostatic interactions and hydrogen bondsbetween amino acid derivatives and P5-Bodipy enable our sensor system to discriminate asparagine from other amino acids. The selective interaction of P5-Bodipy and asparagine provides a ratiometric response with a blue shifting while the fluorescence intensity of P5-Bodipy increases. For practical applications, it provides a crucial advantage over other improved chemosensors which are restricted to single wavelength detection.