Triarylborane substituted naphthalimide as a fluoride and cyanide ion sensor

Abstract

Triarylborane substituted naphthalimide 3 was designed and synthesized by the Sonogashira cross-coupling reaction. The electronic absorption and emission spectra of the triarylborane naphthalimide 3 show red shifted absorption and emission as compared to 4-bromonaphthalimide 2. The sensing behaviour of 3 was studied for different anions. The triarylborane naphthalimide 3 selectively detects F- and CN- ions in the presence of Cl-, Br-, I- and NO2- ions. The effect of F- and CN- ions on the structure of 3 was studied by performing DFT calculations. The theoretical calculations show good agreement with the experimental results. The detection limits for F- and CN- were found to be 2.01 × 10-10 M and 3.94 × 10-10 M respectively. © The Royal Society of Chemistry 2016.