Design rules for oxoporphyrinogen ('OxP') as a versatile chromophore for efficient singlet oxygen generation

0571415 - ÚACH 2024 RIV SG eng J - Článek v odborném periodiku
Hynek, Jan - Chahal, M. K. - Payne, D. T. - Liyanage, A. - D'Souza, F. - Hill, J. P.
Design rules for oxoporphyrinogen ('OxP') as a versatile chromophore for efficient singlet oxygen generation.
Journal of Porphyrins and Phthalocyanines. Roč. 27, č. 7 (2023), s. 1108-1118. ISSN 1088-4246. E-ISSN 1099-1409
Institucionální podpora: RVO:61388980
Klíčová slova: Oxoporphyrinogen * porphyrinoid * singlet oxygen generator
Obor OECD: Inorganic and nuclear chemistry
Impakt faktor: 1.5, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1142/S1088424623500359

Meso-5,10,15,20-tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylideneporphyrinogen, OxP, is a versatile, highly colored chromophore with strong broad absorption in the visible range. It is derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin by two-electron oxidation, and the OxP tetrapyrrole moiety exists in a saddle conformation. N-Alkylation of the OxP core nitrogen atoms can be used to functionalize the chromophore leading to a class of stable molecules with highly substituted peripheries. Substituted OxPs can act as singlet oxygen generators under light irradiation and the efficacy of this process is influenced by the multiplicity of N-substitution, and by the chemical identity of those substituents. Bromination of the macrocyclic beta-positions can also be used to control singlet oxygen generation by the relevant derivatives. We report the quantum yields of singlet oxygen generation for a series of differently substituted OxP derivatives whose metrics indicate that these compounds possess significant potential in the corresponding applications including photodynamic therapy, bacterial inactivation therapy, and organic transformations.
Trvalý link: https://hdl.handle.net/11104/0344466