Gold as a coordinator of an imidazole conjugated dye of BODIPY derivatives for the identification of simple mercaptans

Abstract

Rapid detection of mercaptans in materials and the environment is of great help to material analysis and pollutant monitoring. Gold (Au) shows a high affinity to mercaptans. The coordination and steric effect of mercaptans to Au may be used for the development of new fluorescent sensors. It is possible to distinguish simple mercaptans (such as, HS-, thioglycolic acid) from glutathione (GSH) using Au as a coordinator of dye. Herein, a water-soluble fluorescent sensor of an imidazole conjugated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivative (BIM) was characterized by spectroscopic methods. BIM showed a large Stokes shift and high affinity to metals. Especially, Au-combined BIM produced a new complex BIMAu showing improved fluorescence emission, which can be quenched by thioglycolic acid and sodium hydrosulfide, but less affected by GSH. The detection limit of thioglycolic acid was 0.014 µM. Both NaSH and thioglycolic acid coordinated with BIMAu, while GSH took Au3+ away from BIMAu. These results indicate that the gold coordination competition between imidazole-substituted dyes and mercaptans is a good method for the development of new fluorescence chemosensors.