Version 1
: Received: 20 June 2024 / Approved: 20 June 2024 / Online: 21 June 2024 (13:35:38 CEST)
How to cite:
Millheim, A. C.; Ponzano, E.; Moyano, A. Substituent Effects in the Photophysical and Electrochemical Properties of meso-Tetraphenylporphyrin Derivatives. Preprints2024, 2024061464. https://doi.org/10.20944/preprints202406.1464.v1
Millheim, A. C.; Ponzano, E.; Moyano, A. Substituent Effects in the Photophysical and Electrochemical Properties of meso-Tetraphenylporphyrin Derivatives. Preprints 2024, 2024061464. https://doi.org/10.20944/preprints202406.1464.v1
Millheim, A. C.; Ponzano, E.; Moyano, A. Substituent Effects in the Photophysical and Electrochemical Properties of meso-Tetraphenylporphyrin Derivatives. Preprints2024, 2024061464. https://doi.org/10.20944/preprints202406.1464.v1
APA Style
Millheim, A. C., Ponzano, E., & Moyano, A. (2024). Substituent Effects in the Photophysical and Electrochemical Properties of meso-Tetraphenylporphyrin Derivatives. Preprints. https://doi.org/10.20944/preprints202406.1464.v1
Chicago/Turabian Style
Millheim, A. C., Enric Ponzano and Albert Moyano. 2024 "Substituent Effects in the Photophysical and Electrochemical Properties of meso-Tetraphenylporphyrin Derivatives" Preprints. https://doi.org/10.20944/preprints202406.1464.v1
Abstract
Visible-light photocatalysis, particularly in its application to organic synthesis, has experienced a big renaissance in the past decade. The rational design of new photocatalysts with designed and improved photocatalytic properties, that at the same time circumvents the necessity of using scarce and toxic transition metals, will predictably play a key role in photocatalysis in the next few years. Although free-base porphyrins were identified some years ago as a promising, easily accessible and easily tunable class of organic photoredox catalysts, a systematic study on the effect of the electronic nature and of the position of the substituents on both the ground-state and the excited-state redox potentials of these compounds is still lacking. We have prepared a set of known functionalized derivatives of meso-tetraphenyl porphyrin containing different substituents either in one of the meso-positions or at a beta-pyrrole carbon and we have determined their ground- and (singlet) excited-state redox potentials. This survey has led us to conclude that the introduction of a carbonyl group at the beta-pyrrolic position strongly increases the facility of the monoelectronic reduction of the porphyrin both in the ground state and in the singlet excited state. We have also prepared a second set of four previously unknown benzoyl derivatives of meso-tetraphenylporphyrin, and we have confirmed the validity of our conclusions.
Chemistry and Materials Science, Organic Chemistry
Copyright:
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