Journal of Fluorescence, volume 26, issue 6, pages 2105-2112
Fluorescent Properties of BODIPY Sensors Based on Photoinduced Electron Transfer
Yu S Marfin
1
,
M V Shipalova
1
,
V O Kurzin
1
,
K V Ksenofontova
1
,
A. V. Solomonov
1
,
E V Rumyantsev
1
Publication type: Journal Article
Publication date: 2016-08-16
Journal:
Journal of Fluorescence
scimago Q3
wos Q3
SJR: 0.390
CiteScore: 4.6
Impact factor: 2.6
ISSN: 10530509, 15734994
Biochemistry
Spectroscopy
Clinical Biochemistry
Law
Sociology and Political Science
Social Sciences (miscellaneous)
Clinical Psychology
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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