title: Fluorescent Properties of BODIPY Sensors Based on Photoinduced Electron Transfer.
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.
authors.affiliation: Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia. ymarfin@gmail.com.
authors.forename: Yu S
authors.initials: YS
authors.lastname: Marfin
authors.affiliation: Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia.
authors.forename: M V
authors.initials: MV
authors.lastname: Shipalova
authors.affiliation: Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia.
authors.forename: V O
authors.initials: VO
authors.lastname: Kurzin
authors.affiliation: Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia.
authors.forename: K V
authors.initials: KV
authors.lastname: Ksenofontova
authors.affiliation: Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia.
authors.forename: A V
authors.initials: AV
authors.lastname: Solomonov
authors.affiliation: Department of Inorganic Chemistry, Ivanovo State University of Chemistry and Technology, 7 Sheremetevsky av, 153000, Ivanovo, Russia.
authors.forename: E V
authors.initials: EV
authors.lastname: Rumyantsev
keywords: BODIPY; Computer modeling; Electron-transfer; Fluorescence; pH-sensor