In this contribution, we designed and developed 7-diethylamino-4-hydroxycoumarin coupled anthranilic acid-based enamine (DHCBA) and its Cu2+ complex (DHCBA-Cu)via a simple synthetic strategy. DHCBA shows solvatochromic effect, aggregation induced emission feature at (80 %) methanol–water mixture and colorimetric as well as fluorescence turn-off sensing features towards Cu2+ ions. The DHCBA-Cu2+ ensemble has been utilized as a turn-on fluorescence sensor for the detection of S2− through a decomplexation approach. The formation of a 1:1 DHCBA-Cu2+ ensemble was further supported by 1H NMR studies, HRMS analysis and Density Functional Theory (DFT) calculation. The detection limit for Cu2+ was found to be 6.5 nM and then the binding affinity and binding stoichiometry of the probe towards Cu2+ ion was calculated using the online BindFit v0.5 supramolecular software. Moreover, the 1:1 stoichiometric ratio between DHCBA and Cu2+ ions were confirmed via single crystal X-ray analysis. The structural analysis of DHCBA-Cu2+ indicates that it forms an interesting one-dimensional coordination polymeric chain-like structure, further transformed into a two-dimensional polymeric network through hydrogen bonding interactions. The reversible on–off–on emission character of the probe, DHCBA was successfully applied for the construction of the IMPLICATION logic gate as well as on-site detection applications using paper strip and cotton-swab tests. Furthermore, the sensing feature of the enamine against Cu2+/S2− ions were validated by intracellular imaging applications.
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