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First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays

In this work, the synthesis, characterization and photophysical assays of a new trans-A(2)B-corrole derivative from the naturally occurring quinone are described. β-Lapachone is a naturally occurring quinoidal compound that provides highly fluorescent heterocyclic compounds such as lapimidazoles. Th...

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Detalles Bibliográficos
Autores principales: Rodrigues, Bruna M., Diniz, Carlos C., da Rocha, Vinicius N., Köhler, Mateus H., Brandão, Guilherme P., Machado, Luana A., da Silva Júnior, Eufranio N., Iglesias, Bernardo A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10089255/
https://www.ncbi.nlm.nih.gov/pubmed/37056965
http://dx.doi.org/10.1039/d3ra00823a
Descripción
Sumario:In this work, the synthesis, characterization and photophysical assays of a new trans-A(2)B-corrole derivative from the naturally occurring quinone are described. β-Lapachone is a naturally occurring quinoidal compound that provides highly fluorescent heterocyclic compounds such as lapimidazoles. The new trans-A(2)B-corrole compound was obtained from the reaction between 2,3,4,5,6-(pentafluorophenyl)dipyrromethane and the lapimidazole bearing an aldehyde group. The dyad was characterized by high-resolution mass spectrometry (HRMS), NMR spectroscopy ((1)H, COSY 2D, HMBC, (19)F), FT-IR, UV-vis, steady-state and time-resolved fluorescence, electrochemical studies (CV), TD-DFT analysis and photobiological experiments, in which includes aggregation, stability in solution, photostability and partition coefficients assays. Finally, ROS generation assays were performed using 1,3-diphenylisobenzofuran (DPBF) method and the presented compound showed significant photostability and singlet oxygen production.