Issue 8, 2011

An efficient naphthalimide based fluorescent dyad (ANPI) for F and Hg2+ mimicking OR, XNOR and INHIBIT logic functions

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, –CH[double bond, length as m-dash]N– and anthracene ring protons.

Graphical abstract: An efficient naphthalimide based fluorescent dyad (ANPI) for F− and Hg2+ mimicking OR, XNOR and INHIBIT logic functions

Supplementary files

Article information

Article type
Paper
Submitted
24 Jan 2011
Accepted
17 May 2011
First published
23 Jun 2011

New J. Chem., 2011,35, 1690-1700

An efficient naphthalimide based fluorescent dyad (ANPI) for F and Hg2+ mimicking OR, XNOR and INHIBIT logic functions

M. Shahid, P. Srivastava and A. Misra, New J. Chem., 2011, 35, 1690 DOI: 10.1039/C1NJ20058E

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