Article Design rules for oxoporphyrinogen (‘OxP’) as a versatile chromophore for efficient singlet oxygen generation

Jan Hynek ; Mandeep K. Chahal ; Daniel T. Payne ORCID (National Institute for Materials Science) ; Anuradha Liyanage ; Francis D’Souza ; Jonathan P. Hill SAMURAI ORCID (National Institute for Materials Science)

HILL_Ms_jpp220284_R1.pdf
Download file (1.28 MB)
Download as zip (1.19 MB)
Collection

Citation
Jan Hynek, Mandeep K. Chahal, Daniel T. Payne, Anuradha Liyanage, Francis D’Souza, Jonathan P. Hill. Design rules for oxoporphyrinogen (‘OxP’) as a versatile chromophore for efficient singlet oxygen generation. Journal of Porphyrins and Phthalocyanines. 2023, 27 (07n10), 1108-1118. https://doi.org/10.1142/s1088424623500359
SAMURAI

Description:

(abstract)

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 β-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.

Rights:

Keyword: Oxoporphyrinogen, porphyrinoid, singlet oxygen generator

Date published: 2023-04-06

Publisher: World Scientific Pub Co Pte Ltd

Journal:

  • Journal of Porphyrins and Phthalocyanines (ISSN: 10884246) vol. 27 issue. 07n10 p. 1108-1118

Funding:

Manuscript type: Author's version (Accepted manuscript)

MDR DOI: https://doi.org/10.48505/nims.4954

First published URL: https://doi.org/10.1142/s1088424623500359

Related item:

Other identifier(s):

Contact agent:

Updated at: 2024-11-14 16:30:15 +0900

Published on MDR: 2024-11-14 16:30:16 +0900

Filename Size
Filename HILL_Ms_jpp220284_R1.pdf (Thumbnail)
application/pdf 		Size 1.28 MB Detail