Triarylborane-triphenylamine based luminophore for the mitochondria targeted live cell imaging and colorimetric detection of aqueous fluoride

Abstract

Bioimaging of subcellular organelles such as mitochondria is crucial for detecting physiological abnormalities induced by fluctuations in the levels of various analytes. Herein, we report the design and synthesis of two novel water-soluble cationic Lewis acid triarylborane-triarylamine conjugates 1 and 2. The optical characteristics of 1 and 2 and their precursor compounds BTPA-NMe₂ and BTPA-2NMe₂ were evaluated, which show similar absorption and fluorescence spectra, with 1 and 2 exhibiting higher quantum yields of 0.73 and 0.64, respectively, than those of the precursors BTPA-NMe₂ and BTPA-2NMe₂, indicating the partial disruption of the ICT process and the activation of alternative emission bands in 1 and 2. The live cell imaging ability of compound 2 was examined in HeLa cells using a confocal microscope. Moreover, mitochondrial internalisation using compound 2 was effective and it was found to have high photostability under UV light conditions. Furthermore, compound 2 demonstrated an evident colorimetric response with a colour change to dark yellow in aqueous environments, indicating that it could be used for anion sensing. The spectral changes were observed in UV-visible and fluorescence titration experiments, which were strongly supported by DFT calculations. In short, compound 2 synthesized by us can be exclusively utilized for the selective localization of mitochondria with less cytotoxicity and shows excellent colorimetric response to aqueous inorganic fluoride at levels as low as 0.1 ppm with high selectivity.