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Issue 43, 2015
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Efficient intersystem crossing using singly halogenated carbomethoxyphenyl porphyrins measured using delayed fluorescence, chemical quenching, and singlet oxygen emission

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Abstract

Sensitizers with high triplet quantum yields are useful for generating photovoltaics, photocatalysts and photodynamic therapy agents with increased efficiency. In this study, the heavy atom effect was used to optimize the triplet and singlet oxygen quantum yields of 5,10,15,20-tetrakis(4-carbomethoxyphenyl)porphyrin (1-TCM4PP). The triplet quantum yields, determined using delayed fluorescence, was calculated as 0.35 for 1-TCM4PP, 0.75 for 5,10,15-tris(4-carbomethoxyphenyl)-20-(4-bromophenyl)porphyrin (2-TBCM3PP) and 0.88 for 5,10,15-tris(4-carbomethoxyphenyl)-20-(4-iodophenyl)porphyrin (3-TCM3IPP). Chemical quenching of 1,3-diphenylisobenzofuran and singlet oxygen emission studies rendered an average singlet oxygen quantum yield of 0.51, 0.75, and 0.90 for TCM4PP, TBCM3PP and TCM3IPP respectively. These photophysical properties indicate that a single halogen atom is capable of transforming TCM4PP into a sensitizer with strong triplet character. This is useful for generating singlet oxygen for photodynamic therapy, creating a long lasting reactive species for catalysis and for extending diffusion lengths in photovoltaic applications while retaining three molecular modification points for further functionalization.

Graphical abstract: Efficient intersystem crossing using singly halogenated carbomethoxyphenyl porphyrins measured using delayed fluorescence, chemical quenching, and singlet oxygen emission

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Article information


Submitted
25 Jul 2015
Accepted
05 Oct 2015
First published
06 Oct 2015

Phys. Chem. Chem. Phys., 2015,17, 29090-29096
Article type
Paper
Author version available

Efficient intersystem crossing using singly halogenated carbomethoxyphenyl porphyrins measured using delayed fluorescence, chemical quenching, and singlet oxygen emission

D. M. Marin, S. Payerpaj, G. S. Collier, A. L. Ortiz, G. Singh, M. Jones and M. G. Walter, Phys. Chem. Chem. Phys., 2015, 17, 29090
DOI: 10.1039/C5CP04359J

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