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Detailed Nuclear Magnetic Resonance (NMR) spectroscopy investigations on a novel naphthalene-substituted 1,2,3-triazole-based fluorescence sensor provided evidence for the “turn-on” detection of anions. The one-step, facile synthesis of the sensors was implemented using the “Click chemistry” approach in good yield. When investigated for selectivity and sensitivity against a series of anions (F−, Cl−, Br−, I−, H2PO4−, ClO4−, OAc−, and BF4−), the sensor displayed the strongest fluorometric response for the fluoride anion. NMR and fluorescence spectroscopic studies validate a 1:1 binding stoichiometry between the sensor and the fluoride anion. Single crystal X-ray diffraction evidence revealed the structure of the sensor in the solid state.