A fluorescent probe for selective detection of boric acids and its application for screening the conversion of the Suzuki–Miyaura coupling reaction

Abstract

Boric acid (B(OH)₃) plays an important physiological role and is widely used as a food preservative and an antiseptic. Various colorimetric, fluorescent probes have been developed to detect boric acid; however, most of them could not discriminate boric acid over boronic acids (R–B(OH)₂) or are limited to boronic acid sensors. Therefore, the development of boric acid-selective probes is necessary. Herein, a salicylimine-based fluorophore, Di-OH, was designed that showed selective fluorescence response to boric acid over boronic acid. Its fluorescence response to boric acid showed a large fluorescence turn-on signal up to 140 fold and excellent selectivity with various analytes. Furthermore, since boric acid is generated in proportion to the consumed boronic acid derivatives during reactions involving oraganoboron compounds, Di-OH allowed the determination of the conversion of the Suzuki–Miyaura coupling reaction using fluorescence spectroscopy and its correlation with the GC conversion was confirmed.