A new hydroxynaphthyl benzothiazole derived fluorescent probe for highly selective and sensitive Cu(2+) detection

Abstract

A new reactive probe, 1-(benzo[d]thiazol-2-yl)naphthalen-2-yl-picolinate (BTNP), was designed and synthesized. BTNP acts as a highly selective probe to Cu(2+) in DMSO/H2O (7/3, v/v, Tris-HCl 10mM, pH=7.4) solution based on Cu(2+) catalyzed hydrolysis of the picolinate ester moiety in BTNP, which leads to the formation of an ESIPT active product with dual wavelength emission enhancement. The probe also possesses the advantages of simple synthesis, rapid response and high sensitivity. The pseudo-first-order reaction rate constant was calculated to be 0.205min(-1). Moreover, application of BTNP to Cu(2+) detection in living cells and real water samples was also explored.

Keywords: Benzothiazole; Cell imaging; Cu(2+) catalyzed hydrolysis; Cu(2+) recognition; ESIPT.