Publication details

Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts

Authors

MARTÍNEK Marek VANA Jiri ŠEBEJ Peter NAVRATIL Rafael SLANINA Tomáš LUDVÍKOVÁ Lucie ROITHOVÁ Jana KLÁN Petr

Year of publication 2020
Type Article in Periodical
Magazine / Source ChemPlusChem
MU Faculty or unit

Faculty of Science

Citation
Web https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202000370
Doi http://dx.doi.org/10.1002/cplu.202000370
Keywords DFT calculations; dyes; pigments; photochemistry; reaction mechanisms; spectroscopy
Description Leaving groups attached to themeso-methyl position of many common dyes, such as xanthene, BODIPY, or pyronin derivatives, can be liberated upon irradiation with visible light. However, the course of phototransformations of such photoactivatable systems can be quite complex and the identification of reaction intermediates or even products is often neglected. This paper exemplifies the photochemistry of a 9-dithianyl-pyronin derivative, which undergoes an oxidative transformation at themeso-position to give a 3,6-diamino-9H-xanthen-9-one derivative, formic acid, and carbon monoxide as the main photoproducts. The course of this multi-photon multi-step reaction was studied under various conditions by steady-state and time-resolved optical spectroscopy, mass spectrometry and NMR spectroscopy to understand the effects of solvents and molecular oxygen on individual steps. Our analyses have revealed the existence of many intermediates and their interrelationships to provide a complete picture of the transformation, which can bring new inputs to a rational design of new photoactivatable pyronin or xanthene derivatives.
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