Abstract
A novel Schiff base with AIEE characteristics has been developed and used as a chemosensor for picric acid in aqueous media. The Schiff base 1-((E)-((E)-(4-(benzyloxy) benzylidene) hydrazono) methyl) naphthalen-2-ol [BBHN] with strong fluorescence emission was obtained by the simple condensation of 1-(hydrazonomethyl)naphthan-2-ol and 4-benzoxy benzaldehyde. The characterization of BBHN was done using Fourier Transfer Infra-Red, UV–visible, Magnetic Resonance (1H and 13C) spectroscopy, and HRMS. The sensing behaviour of BBHN aggregates towards nitro explosive was then investigated. The aggregates of BBHN showed a quick, highly selective, and sensitive fluorescence ‘Turn Off’ response towards picric acid (PA) in an aqueous medium among various other nitroaromatics. The limit of detection was 4.04 µM with 2.03 × 106 M−1 as the quenching constant. The fluorescence “Turn Off” response in the presence of PA is mainly due to π-π interactions, and non-covalent hydrogen bonding interactions. Moreover, steady-state fluorescence lifetime measurement and Stern − Volmer plots reveal that the fluorescence quenching followed mixed quenching strategies.
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