A highly selective triphenylamine-based indolylmethane derivatives as colorimetric and turn-off fluorimetric sensor toward Cu2+ detection by deprotonation of secondary amines

A new triphenylamine-based fluorogenic probe bearing an indolylmethane unit (R1) was developed as a fluorescent chemosensor with high selectivity toward Cu2+ over other cations tested. The new probe R1 only sensed Cu2+ among heavy and transition metal (HTM) ions in CH3CN/H2O (70/30, v/v) solution. The capture of Cu2+ by the receptor resulted in deprotonation of the secondary amine conjugated to the triphenylamine, so that the electron-donation ability of the “N” atom would be greatly enhanced; thus sensor showed a 250 nm change in the new absorption band (from 291 nm to 541 nm) and a large colorimetric response, it also exhibited the large decrease in fluorescence intensity at 378 nm and affinity to Cu2+ over other cations such as Hg2+, Fe3+, Pb2+, Zn2+, Cd2+, Ni2+, Co2+ and Mn2+ make this compound a useful chemosensor for Cu2+ detection in CH3CN/H2O (70/30, v/v) mixture. The probe R1 (c = 1.0 × 10−6 M) displayed significant fluorescence change and colorimetric change upon addition of Cu2+ among the metal ions examined.