A naphthalene-thiophene hybrid molecule as a fluorescent AND logic gate with Zn2+ and OAc- ions as inputs: cell imaging and computational studies.

Debasis Karak, Sudipta Das, Sisir Lohar, Arnab Banerjee, Animesh Sahana, Ipsit Hauli, Subhra Kanti Mukhopadhyay, Damir A Safin, Maria G Babashkina, Michael Bolte, Yann Garcia, Debasis Das

Index: Dalton Trans. 42(19) , 6708-15, (2013)

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Abstract

A naphthalene-thiophene hybrid molecule (Z)-1-((thiophen-2-ylmethylamino)methylene)naphthalen-2(1H)-one () was prepared by condensation of 2-thiophenemethylamine and 2-hydroxy-1-naphthaldehyde. According to FTIR, (1)H NMR spectrometry and single crystal X-ray analysis, exists in the cis-keto-amine tautomeric form. 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 and its zinc acetate complex were also optimized by DFT calculations. binds Zn(2+) in a 1 : 1 ratio with an association constant K(a) = 2.05 × 10(4) M(-1), and detects Zn(2+) as low as 3 × 10(-8) M. is useful for the detection of intracellular Zn(2+) under a fluorescence microscope.