Construction Of Naphthalimide Arylacetonitrile Reaction And Investigation Of Its Anion Recognition

The recognition and sensing of anions has become one of the most important fields of supramolecular chemistry,which is attributed to the important role played by anions in environmental and many biological processes.In the field of anion recognition,anion probes have attracted wide attention from scientific researchers due to their high selectivity and sensitivity to anions,as well as economic,simple and easy to operate.Based on the previous research of our group,this project exploring 1,8-naphthimide as the fluorophore and the activated-CHCN group as the recognition site,a novel cyanide probe 4 with the skeleton of the activated C-H groupfluorophore-directed group was successfully designed and synthesized by regioselective directing arylacetonitrile in naphthalimide.A series of experimental studies such as UV-visible titration and 1H NMR titration have shown that the probe has the characteristics such as high selectivity,good sensitivity,reversibility and reproducibility for the sensing of cyanide.Also,the "naked eye" detection of cyanide ions by probe 4 was achieved in aqueous solution and on solid test paper.Further,we developed a simple method for synthesis of Naphthalimide Arylacetonitrile derivatives through the trifluoromethyl-directed arylacetonitrile reaction in 2-position of 1,8-naphthalimide.By optimizing the conditions,α,α-diarylacetonitrile derivatives 3a-j were obtained at moderate yields under basic conditions.And its ability of sensing anion was studied in detail.This method provides a new way for preparing α,α-Naphthalimide Arylacetonitrile derivatives as well as development of anion sensors containing an active-CH recognition site with the advantage such as simple operation,high regioselectivity,reaction at room temperature and no transition metal catalysts and ligands required.