Pyrenebutylamidopropylimidazole as a multi-analyte sensor for 3,5-dinitrosalicylic acid and Hg2+ ions

Pyrenebutylamidopropylimidazole 1 was synthesized as a sensor for 3,5-dinitrosalicylic acid (3,5-DNSA) and 5-nitrosalicylic acid (5-NSA), among other aromatic carboxylic acids, and Hg2+ among different metal ions in PBS-EtOH (5:95; pH=7.4) solutions. The sensing ability of probe 1 was examined using fluorescence and H-1 NMR spectroscopy. The presence of 3,5-DNSA and 5-NSA resulted in 97% and 50% quenching, respectively, of the emission intensity at lambda(max)=379 nm of probe 1, whereas the presence of Hg2+ resulted in the selective development of an excimer band at 476 nm with simultaneous quenching of the monomer emission. Probe 1 had good association constants with 3,5-DNSA (K-a=4.38 x 10(4) M-1) and 5-NSA (K-a=2.37 x 10(4) M-1) in a 1:1 stoichiometry in PBS-EtOH (5:95; pH=7.4) solution, whereas the presence of Hg2+ led to the formation of a 1:2 complex between Hg2+ and probe 1 with a high association constant (K-a=9.76 x 10(4) M-1). These results were further supported by energy-minimization density functional theory calculations. (C) 2015 Elsevier B.V. All rights reserved.