Issue 16, 2023

First report of trans-A2B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays

Abstract

In this work, the synthesis, characterization and photophysical assays of a new trans-A2B-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-A2B-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 (1H, COSY 2D, HMBC, 19F), 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.

Graphical abstract: First report of trans-A2B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays

Supplementary files

Article information

Article type
Paper
Submitted
07 Feb 2023
Accepted
01 Apr 2023
First published
11 Apr 2023
This article is Open Access
Creative Commons BY license

RSC Adv., 2023,13, 11121-11129

First report of trans-A2B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays

B. M. Rodrigues, C. C. Diniz, V. N. da Rocha, M. H. Köhler, G. P. Brandão, L. A. Machado, E. N. da Silva Júnior and B. A. Iglesias, RSC Adv., 2023, 13, 11121 DOI: 10.1039/D3RA00823A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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