First report of -AB-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays

• Published in: RSC advances 2023-04, Vol.13 (16), p.11121-11129
• Main Authors: 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
• Format: Article
• ISSN: 2046-2069
• DOI: 10.1039/d3ra00823a

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. Photophysical properties of novel corroles containing lapachol units. DFT calculations and electrochemical analysis were conducted to better understand the corrole molecular structures. Corrole derivatives do not form aggregates in solution and generate ROS species.