Effect of substituents of corrole derivatives on generation of singlet oxygen

[Display omitted] •A structure-property relationship on the generation of singlet oxygen has been studied.•Depending on the substituents, the quantum yield and lifetime of singlet oxygen were varied.•The photophysical and electrochemical properties were investigated along with DFT calculations. The...

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Bibliographic Details
Published in:Chemical physics letters 2021-01, Vol.763, p.138165, Article 138165
Main Authors: Shin, Jun-Yong, Kim, Seung-Hwan, Lee, Sunhee, Lee, Yong Sup, Han, Won-Sik, Wang, Kang-Kyun
Format: Article
Language:English
Subjects:
Corrole
Phosphorescence
Photodynamic therapy
Photosensitizer
Singlet oxygen
Triplet quantum yield
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Summary:[Display omitted] •A structure-property relationship on the generation of singlet oxygen has been studied.•Depending on the substituents, the quantum yield and lifetime of singlet oxygen were varied.•The photophysical and electrochemical properties were investigated along with DFT calculations. The correlation between the molecular structures of three corrole derivatives (PC: 5,10,15-triphenyl corrole, PFPC: 5,10,15-tris(pentafluorophenyl) corrole, MCPC: 5,10,15-tris(p-methoxycarbonylphenyl)corrole) and their efficiencies for singlet oxygen generation was studied. Introducing electron-withdrawing fluorine atoms into the PC moiety led to a significant enhancement in singlet oxygen generation and facilitated intersystem crossing (ISC) due to enhanced spin-orbit coupling. Cyclic voltammetry experiments revealed a desirable linear relationship between the quenching rate constants and the oxidation potentials of the three corrole derivatives, indicating that the substituent effect is a critical factor governing the oxidation potential of photosensitizers for singlet oxygen generation.
ISSN:0009-2614
DOI:10.1016/j.cplett.2020.138165