High-contrast colourimetric probes for fluoride and trace water based on tautomerization of naphthalimide and application in fingerprint imaging

Three probes for fluoride ion and trace water based on naphthalimide were designed and synthesized. A new sensing mechanism based on naphthalimide tautomerization induced by fluoride ion and water was explored in the aprotic organic solvent. In the fluoride ion sensing process, the probes exhibited a remarkable absorption peak centred at 560 nm in the visible range of 400–700 nm. When trace water presented, the newly formed absorption peak centred at 560 nm gradually disappeared. The sensitive colour variation of the probe also was used in fingerprint imaging. Accordingly, the significant changes in chemical shift of dept135 and 1HNMR spectrum confirmed the structural transformation of the probes with high contrast. Furthermore, this work also presented an optimization strategy for the sensitivity of the probe based on regulatory tautomerization.