Experimental and theoretical studies of carbazole-based Schiff base as a fluorescent Fe3+ probe

Abstract

Synthesis of a new (E)-N1-((9-ethyl-9H-carbazol-3-yl)methylene)-5-nitrobenzene-1,2-diamine as a fluorescent chemosensor for selective detection of Fe3+ ion over a number of other metal ions is described. The method for the synthesis of the carbazole Schiff base was based on the condensation of carbazole-3-carbaldehyde with 4-nitro-o-phenyldiamine in dimethylformamide in a moderate yield. The structure of the final compound was characterized by H-1 NMR, (13) C NMR, IR, mass spectrometry, and single crystal X-ray diffraction. The final compound exhibited exceptional selective and sensitive turn-on fluorescence response to the Fe3+ cation. The fluorescent intensity of the final compound was increased 20-fold and the stoichiometry ratio of the final compound to Fe3+ was 1:1. The association constant and detection limit for Fe3+ ion were predicted from fluorescence titrations as (1.36 +/- 0.09).10(4) M-1 and 1.0 to 6.0 mu M, respectively. The photophysical behavior of the compound was further explored by DFT methods. The predicted UV-Vis spectrum by TDDFT calculations was compared to the observed absorption spectrum of the targeted compound.