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A Beneficial Effect of Bromination on the Photophysical and Photochemical Properties of Aza‐BODIPY Dyes with Electron‐Donating Groups

A Beneficial Effect of Bromination on the Photophysical and Photochemical Properties of... A series of aza‐BODIPY dyes substituted with meta‐(dimethylamino)phenyl groups were synthesized and their spectroscopic, photophysical, and electrochemical properties were compared. Highly desirable photophysical and photochemical properties were induced in meta‐(Me2N)Ph‐substituted aza‐BODIPY by bromination of the aromatic rings at the 3 and 5 positions. In particular, high values of singlet oxygen quantum yields (ΦΔ) were measured, ranging from 0.36 to 0.58. The photosensitized oxygenation process of a model compound – diphenylisobenzofuran (DPBF) ‐ proceeds via a Type II mechanism for the di‐bromo derivative, while for the tetra‐bromo derivative a mixed mechanism involving both 1O2 and other reactive forms of oxygen formation (Type I and/or Type III) was detected. Nanosecond laser photolysis experiments of the brominated aza‐BODIPYs revealed T1→Tn absorption spanning from ca. 350 nm to ca. 510 nm with the triplet lifetimes (τT) ranged between 15.6 μs and 26.0 μs. The brominated aza‐BODIPYs studied exhibited an absorption band within the so‐called “therapeutic window”, with λabs located between 620 nm and 636 nm. As estimated by CV/DPV measurements, the meta‐(Me2N)Ph‐substituted aza‐BODIPYs studied exhibited a multi‐electron oxidation processes at a relatively low oxidation potentials (Eox), pointing to the very good electron‐donating properties of these molecules. All compounds studied exhibited extremely high photostability and thermal stability. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

A Beneficial Effect of Bromination on the Photophysical and Photochemical Properties of Aza‐BODIPY Dyes with Electron‐Donating Groups

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References (54)

Publisher
Wiley
Copyright
© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201900385
Publisher site
See Article on Publisher Site

Abstract

A series of aza‐BODIPY dyes substituted with meta‐(dimethylamino)phenyl groups were synthesized and their spectroscopic, photophysical, and electrochemical properties were compared. Highly desirable photophysical and photochemical properties were induced in meta‐(Me2N)Ph‐substituted aza‐BODIPY by bromination of the aromatic rings at the 3 and 5 positions. In particular, high values of singlet oxygen quantum yields (ΦΔ) were measured, ranging from 0.36 to 0.58. The photosensitized oxygenation process of a model compound – diphenylisobenzofuran (DPBF) ‐ proceeds via a Type II mechanism for the di‐bromo derivative, while for the tetra‐bromo derivative a mixed mechanism involving both 1O2 and other reactive forms of oxygen formation (Type I and/or Type III) was detected. Nanosecond laser photolysis experiments of the brominated aza‐BODIPYs revealed T1→Tn absorption spanning from ca. 350 nm to ca. 510 nm with the triplet lifetimes (τT) ranged between 15.6 μs and 26.0 μs. The brominated aza‐BODIPYs studied exhibited an absorption band within the so‐called “therapeutic window”, with λabs located between 620 nm and 636 nm. As estimated by CV/DPV measurements, the meta‐(Me2N)Ph‐substituted aza‐BODIPYs studied exhibited a multi‐electron oxidation processes at a relatively low oxidation potentials (Eox), pointing to the very good electron‐donating properties of these molecules. All compounds studied exhibited extremely high photostability and thermal stability.

Journal

Asian Journal of Organic ChemistryWiley

Published: Oct 1, 2019

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