Design,Synthesis And Binding Ability Of Fluorescent Sensors Based On Novel F~- Induced Deprotonation Of The C-H Group Followed By Autoxidative Decvanation Process

Fluoride ions play the key roles in a wide variety of biological, clinical and environmental sciences. Recently, the design and development of artificial fluoride ion receptors with the specific sensing performances have attracted great attention in supramolecular chemistry. Naphthalimide derivatives had been widely applied in the fields of dyes, pigment and fluorescent probe because of its excellent features, such as remarkable photoelectric characteristic, structure stability and facile synthesis.In this paper, a novel naphthalimide derivative with the CHCN group were designed and synthesized by the condensation of N-butyl-4-bromide-1,8-naphthalimide with 2-pyridine acetonitrile. UV-visible, fluorescence and 1H-NMR spectral titration with F-revealed that the probe 4 exhibited the highly specific selectivity as well as high sensitivity toward F", and also achieve the aim of "naked-eye" detectionFurther, we also successfully synthesized a series of a,a-aryl naphthalimide nitriles derivatives (3a-3j) by the condensation of N-butyl-4-bromide-1,8-naphthalimide and substituted phenylacetonitriles. And the spectral differences which the interaction of fluoride bns with different probes 3a-3j, was investigated in detail. Meanwhile, we also developed a novel and facile synthetic procedure for the preparation of a,a-aryl naphthalimide nitrile derivatives (3a-j), which can be used as F-ion sensors and convenient precursors for the synthesis of aryl naphthalimide ketones (4a-j) based on fluoride-induced deprotonation followed by autoxidative decyanation.