Fluorescent Chemosensing Properties of New Isoindoline Based-Receptors towards F^- and Cu²⁺ Ions

Soosai Devaraj, Muthusamy Kandaswamy

Department of Inorganic Chemistry, School of Chemical Sciences, University of Madras, Chennai, India.

DOI: 10.4236/opj.2013.31006                

Abstract

Two simple colorimetric and fluorescent anion chemosensors based on amide moieties, 4-nitro-N-[(1,3-dioxoisoindolin-2yl)benzamide (1), 3,5-dinitro-N-[(1,3-dioxoisoindolin-2yl)benzamide (2) have been synthesized and characterized. Comparing with other anions studied, the UV-visible absorption spectrum in DMSO shows significant response toward F^- ion with high selectivity, and meanwhile color change is observed from colorless to pink and violet for 1 and 2 respectively in the presence of tetrabutylammonium fluoride (TBAF) (5 × 10^-3 M). Moreover, F^--induced color changes remain the same even in the large excess of Cl^- , Br^- and I^-. In addition, the ¹H NMR spectrum titration in DMSO-d₆ shows deprotonation of the receptors 1 and 2 in the presence of basic F^- ion. In particular, addition of F^- to the receptors 1 and 2 resulted in an enhancement in fluorescence intensity at 770 nm. Both receptors 1 and 2 exhibit a fluorescent emission enhancement when addition of Zn²⁺, Ni²⁺, Co²⁺, Cu²⁺ and Mn²⁺ metal ions. The fluorescent enhancement values for the receptor 1 are 2.29 (Cu²⁺), 1.85 (Ni²⁺), 1.37 (Co²⁺), 1.27 (Mn²⁺), 1.25 (Zn²⁺) and for 2, 2.57 (Cu²⁺), 1.66 (Ni²⁺), 1.36 (Co²⁺), 1.15 (Mn²⁺), 1.09 (Zn²⁺). The selectivity of Cu²⁺ is higher for 1 and 2 than other metal ions such as Zn²⁺, Ni²⁺, Co²⁺ and Mn²⁺.

Keywords

Chemosensors; Colorimetric; Fluoride; Napththalimide; Cations; Copper(II) Sensor; Fluorescence

Conflicts of Interest

The authors declare no conflicts of interest.

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