A new colorimetric chemodosimeter for Hg2+ based on charge-transfer compound of N-methylpyrrole with TCNQ

Reaction of N-methylpyrrole and 7,7,8,8-tetracyanoquinodimethane (TCNQ) furnishes an intense blue unsymmetrical charge-transfer compound through regioselective attachment of tricyanoquinodimethane at the 2-position of N-methylpyrrole which was found to be selective chemodosimeter for Hg2+ ions in CH3CN:H2O mixture (1:1 v/v, pH = 7.0, 0.01 M HEPES. 0.15 M NaCl) as well as in the solid state when supported on silica, over a variety of metal ions. A plausible mechanism for the sensing process has been proposed and supported through the characterization of the resulting Hg2+ complex and the density functional theory (DFT) studies. (C) 2010 Elsevier B.V. All rights reserved.