title: A naphthalene-thiophene hybrid molecule as a fluorescent AND logic gate with Zn2+ and OAc- ions as inputs: cell imaging and computational studies.
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.
authors.affiliation: Department of Chemistry, The University of Burdwan, Burdwan, 713104, West Bengal, India.
authors.forename: Debasis
authors.initials: D
authors.lastname: Karak
authors.forename: Sudipta
authors.initials: S
authors.lastname: Das
authors.forename: Sisir
authors.initials: S
authors.lastname: Lohar
authors.forename: Arnab
authors.initials: A
authors.lastname: Banerjee
authors.forename: Animesh
authors.initials: A
authors.lastname: Sahana
authors.forename: Ipsit
authors.initials: I
authors.lastname: Hauli
authors.forename: Subhra Kanti
authors.initials: SK
authors.lastname: Mukhopadhyay
authors.forename: Damir A
authors.initials: DA
authors.lastname: Safin
authors.forename: Maria G
authors.initials: MG
authors.lastname: Babashkina
authors.forename: Michael
authors.initials: M
authors.lastname: Bolte
authors.forename: Yann
authors.initials: Y
authors.lastname: Garcia
authors.forename: Debasis
authors.initials: D
authors.lastname: Das
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002176:Candida albicans / Q000302:isolation & purification; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D008856:Microscopy, Fluorescence; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: C583956:1-((thiophen-2-ylmethylamino)methylene)naphthalen-2(1H)-one; D000085:Acetates; D005456:Fluorescent Dyes; D007477:Ions; D009281:Naphthalenes; D013876:Thiophenes; C031721:naphthalene; C062247:2-hydroxy-1-naphthaldehyde; D015032:Zinc