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A carbamate-linked-bistriazole ( 5 ) was prepared by click reaction of diethynyl 1,3-phenylenedicarbamate ( 2)  and phenyl azide derivative ( 4 ) in DMF/H 2 O using copper sulfate and sodium ascorbate as a catalyst at room temperature for fluoride ion sensing. The structural analysis of synthesized compound was done by using  1 HNMR,  13 C NMR, FTIR and HRMS. The sensing behavior of carbamate-linked-bistriazole ( 5)  was examined by  1 HNMR, UV–vis and fluorescence study. NMR titration study suggested the participation of triazole, amide and aromatic protons in binding of fluoride ion. UV–visible study established the 1:1 complexation ratio between sensor  5  and F –  ion with stability constant K of 2.64 × 10 4  M −1  and detection limit in µM range (9.372 µM). Further, fluorescence titration for  5  (9.2 × 10 −6  M) with fluoride ions exhibited an emission quenching at 424 nm along with small bathochromic shift. Density functional theory (DFT) calculations also confirmed interaction mechanism in  5a -F –  complex established by, UV–visible,  1 H NMR and fluorescence studies.

Synthesis, Characterization, Fluoride Ion Sensing and DFT Studies of Carbamate-Based Bistriazole