10.1039/c1cc10784d
The research focuses on the development of a novel BODIPY dye, which serves as a highly selective, sensitive, and rapid chromogenic and fluorescent chemodosimeter for detecting fluoride anions. The study involves the synthesis of BODIPY dye 3 through a three-step process, starting with the condensation of 2,4,6-trimethylbenzaldehyde and 2,4-dimethylpyrrole, followed by oxidation and chelation to form BODIPY dye 1, iodination to obtain BODIPY dye 2, and finally a Pd-catalyzed Sonogashira reaction with trihexylsilylacetylene to produce BODIPY dye 3. The experiments conducted include the analysis of absorption and fluorescence spectra of the dyes in the presence of increasing fluoride concentrations, demonstrating a significant change in optical and fluorescent characteristics upon interaction with fluoride ions. The research utilized various analytical techniques such as X-ray methods to confirm the structure of BODIPY dye 2, and 1H NMR to detect the formation of BODIPY dye 4 after the reaction with fluoride. Additionally, DFT and TDDFT calculations were employed to corroborate the blue-shift of the absorption band induced by fluoride. The study highlights the dye's potential for use in analytical chemistry and cellular imaging due to its rapid response time and high sensitivity, with a limit of detection in the nM scale.
