A naphthalene-thiophene hybrid molecule as a fluorescent and logic gate with Zn~(2+) and OAc~- ions as inputs: Cell imaging and computational studies

摘要

A naphthalene-thiophene hybrid molecule (Z)-1-((thiophen-2-ylmethylamino) methylene)naphthalen-2(1H)-one (HL) was prepared by condensation of 2-thiophenemethylamine and 2-hydroxy-1-naphthaldehyde. According to FTIR, ~1H NMR spectrometry and single crystal X-ray analysis, HL exists in the cis-keto-amine tautomeric form. HL behaves like a molecular AND type binary logic gate with two inputs viz. Zn~(2+) and OAc- ions whereby the fluorescence of the system turns on. The structures of HL and its zinc acetate complex were also optimized by DFT calculations. HL binds Zn ~(2+) in a 1: 1 ratio with an association constant Ka = 2.05 × 10~4 M~(-1), and detects Zn~(2+) as low as 3 × 10~(-8) M. HL is useful for the detection of intracellular Zn~(2+) under a fluorescence microscope.