Anthracene scaffold as highly selective chemosensor for Al³⁺ and its AIEE activity

Fluorescent chemosensor, 3-(Anthracen-2-yliminomethyl)-benzene-1,2-diol (ANB) has been synthesized by one-step condensation of 2-aminoanthracene and 2,3-dihydroxybenzaldehyde and characterized using ¹H-NMR, FT-IR and Mass spectroscopic techniques. The probe ANB was found to be an efficient ‘turn-on’ fluorescence chemosensor for the selective detection of Al³⁺ ion over other metal ions in an aqueous solution. The chemosensor exhibits ~ 27-fold enhancement of emission intensity in presence of Al³⁺ ion. Fluorescence quantum values for ANB and (Al³⁺-ANB)-complex are 0.004 and 0.097, respectively. In addition, the binding constant and the limit of detection were found to be 1.22 × 10⁴ M⁻¹ and 0.391 µM, respectively. The chemosensor ANB binds to Al³⁺ ions in 2:1 stoichiometric ratio which was supported by Job’s plot, ¹H-NMR titration and florescence titration. Fluorescence reversibility of the sensor complex was well established by adding EDTA in the same condition and a molecular INHIBIT logic gate was fabricated using this reversible nature of the sensor complex. Additionally, the chemosensor ANB shows a novel aggregation-induced enhanced emission phenomenon, where the aggregate hydrosol of ANB shows enhance emission intensity. Graphical abstract: [Figure not available: see fulltext.]