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Literature DB >> 27530633

Fluorescent Properties of BODIPY Sensors Based on Photoinduced Electron Transfer.

Yu S Marfin¹, M V Shipalova², V O Kurzin², K V Ksenofontova², A V Solomonov², E V Rumyantsev².

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.

Entities: Chemical

Keywords: BODIPY; Computer modeling; Electron-transfer; Fluorescence; pH-sensor

Year: 2016 PMID： 27530633 DOI： 10.1007/s10895-016-1905-1

Source DB: PubMed Journal: J Fluoresc ISSN： 1053-0509 Impact factor: 2.217

25 in total

1. Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities.

Authors: Sascha Hoogendoorn; Annet E M Blom; Lianne I Willems; Gijsbert A van der Marel; Herman S Overkleeft
Journal: Org Lett Date: 2011-09-26 Impact factor: 6.005

2. Photophysical properties of BODIPY-derived hydroxyaryl fluorescent pH probes in solution.

Authors: Wenwu Qin; Mukulesh Baruah; Alina Stefan; Mark Van der Auweraer; Noël Boens
Journal: Chemphyschem Date: 2005-11-11 Impact factor: 3.102

Review 3. Fluorescent indicators for intracellular pH.

Authors: Junyan Han; Kevin Burgess
Journal: Chem Rev Date: 2010-05-12 Impact factor: 60.622

4. BODIPY dyes and their derivatives: syntheses and spectroscopic properties.

Authors: Aurore Loudet; Kevin Burgess
Journal: Chem Rev Date: 2007-10-09 Impact factor: 60.622

5. Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ

Authors:
Journal: J Org Chem Date: 2000-06-30 Impact factor: 4.354

6. A reversible fluorescence probe based on Se-BODIPY for the redox cycle between HClO oxidative stress and H2S repair in living cells.

Authors: Bingshuai Wang; Peng Li; Fabiao Yu; Ping Song; Xiaofei Sun; Songqiu Yang; Zhangrong Lou; Keli Han
Journal: Chem Commun (Camb) Date: 2012-12-21 Impact factor: 6.222

3. Bodipy Based Fluorescent Materials in Cellulose Matrices: Synthesis, Spectral Properties and Vapochromic Fluorescent Recognition of Alcohols and Acetone.

Authors: A V Bobrov; M V Kishalova; A A Ksenofontov; S D Usoltsev; Yu S Marfin
Journal: J Fluoresc Date: 2021-08-09 Impact factor: 2.217

3 in total

Fluorescent Properties of BODIPY Sensors Based on Photoinduced Electron Transfer.

1. Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities.

2. Photophysical properties of BODIPY-derived hydroxyaryl fluorescent pH probes in solution.

Review 3. Fluorescent indicators for intracellular pH.

4. BODIPY dyes and their derivatives: syntheses and spectroscopic properties.

5. Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ

6. A reversible fluorescence probe based on Se-BODIPY for the redox cycle between HClO oxidative stress and H2S repair in living cells.

7. Fluorescent Properties of 8-Substituted BODIPY Dyes: Influence of Solvent Effects.

8. Long-wavelength, photostable, two-photon excitable BODIPY fluorophores readily modifiable for molecular probes.

9. Fluorescent properties of 8-phenylBODIPY in ethanol - ethylene glycol mixed solutions.

10. Fluorescent visualization of Src by using dasatinib-BODIPY.

1. Synthesis and Spectral Characteristics of BODIPY Dyes with Two or Three Dipyrrin Domains.

2. Spectral Properties and Possibilities of meso-Substituted BODIPY Usage in Sol-Gel Process and Materials.

3. Bodipy Based Fluorescent Materials in Cellulose Matrices: Synthesis, Spectral Properties and Vapochromic Fluorescent Recognition of Alcohols and Acetone.