Abstract

A fluorescent bischromophoric dyad combining anthracene and naphthalic anhydride units has been synthesized and characterized. The dyad shows a FRET mediated emission signal at ∼535 nm when excited at λex. = 380/360 nm, with efficient energy transfer efficiency (ET = 93%) and quantum yield (Φ = 0.155). Upon interaction with F− and Hg2+ ions selectively, a diminished (switched-Off) FRET signal is observed and the naked-eye sensitive color of the solution changed to dark red with enhanced emission corresponding to an anthracene moiety (switched-On). Job's plot analysis revealed a 1 : 1 stoichiometry between dyad and F−/AcO− and Hg2+ ions. The output fluorescence signals exhibited by dyad on chemical inputs of F−, AcO− and Hg2+ ions mimicked OR, XNOR and INHIBIT logic functions. A 1H NMR titration experiment suggested deprotonation of –NH proton and “Y-type or tweezer-like” H-bonding interaction in the presence of F− and AcO−, respectively, involving –NH, –CHN– and anthracene ring protons.

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