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Published on: June 8, 2020
Fluorescent Properties of BODIPY Sensors Based on Photoinduced Electron Transfer
Yu S Marfin1, M V Shipalova2, V O Kurzin2
1Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia. ymarfin@gmail.com.
Abstract:
Two boron-dipyrrin (BODIPY) based dyes with dimethylaminophenyl and carboxyphenyl substituents in 8-position of dipyrrin ligand have been synthesized and characterized. Photophysical and spectral properties of the obtained compounds have been investigated in water-ethanol mixture and water-cyclohexane system with variation of pH values. The equilibria constants of the compounds were identified by classical methods of acid-base titration. BODIPY bearing dimethylaminophenyl and carboxyphenyl subunits show deprotonation/protonation dependent fluorescence off/on-switching. The change of the emission could be mechanistically explained by a PET (photoinduced electron transfer) from the 8-substituent to the fluorophore. The present study demonstrates that BODIPY-based fluorescent sensors can be used to measure the pH in the range of 2-13 extending the scope of BODIPY dyes available as pH-indicators. Investigated compounds demonstrate weak dye-dye interaction allowing their cooperative usage as indicators.
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