1-(Pyridin-2-ylmethyl)-2-(3-(1-(pyridin-2-ylmethyl)benzimidazol-2-yl) propyl) benzimidazole and its copper(II) complex as a new fluorescent sensor for dopamine (4-(2-aminoethyl)benzene-1,2-diol)

A new ligand 1-(pyridin-2-ylmethyl)-2-(3-(1-(pyridin-2-ylmethyl)benzimidazol-2-yl) propyl) benzimidazole (L) and its Cu(II) complex (1) have been synthesized and characterized spectroscopically and structurally. The Cu(II) ion is coordinated by two nitrogen atoms of benzimidazole groups, two oxygen atoms of the nitrate anions and one oxygen atom of a water molecule forming distorted trigonal bipyramidal geometry. The ligand and its complex have been utilized as a fluorescent sensor for 4-(2-aminoethyl)benzene-1,2-diol. A plot of F-0/F-F-0 vs 1/Conc (4-(2-aminoethyl)benzene-1,2-diol) at a selected wavelength of 306 nm with (L) that shows a straight line behavior, supports the validity of the assumption of 1:1 complex formation and the association constant of (L) with 4-(2-aminoethyl)benzene-1,2-diol is calculated to be 9868 M-1. Sensor (L) is found to be selective for 4-(2-aminoethyl)benzene-1,2-diol over aromatic amines, phenols, amino catechol (L-3,4-dihydroxyphenylalanine) and 4,6-ditertiarybutyl benzene-1,2-diol. (C) 2013 Elsevier B.V. All rights reserved.