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@article{48196,
author = {Martínek, Marek and Vana, Jiri and Šebej, Peter and Navratil, Rafael and Slanina, Tomáš and Ludvíková, Lucie and Roithová, Jana and Klán, Petr},
article_location = {Weinheim},
article_number = {10},
doi = {http://dx.doi.org/10.1002/cplu.202000370},
keywords = {DFT calculations; dyes; pigments; photochemistry; reaction mechanisms; spectroscopy},
language = {eng},
issn = {2192-6506},
journal = {ChemPlusChem},
title = {Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202000370},
volume = {85},
year = {2020}
}
TY - JOUR
ID - 48196
AU - Martínek, Marek - Vana, Jiri - Šebej, Peter - Navratil, Rafael - Slanina, Tomáš - Ludvíková, Lucie - Roithová, Jana - Klán, Petr
PY - 2020
TI - Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts
JF - ChemPlusChem
VL - 85
IS - 10
SP - 2230-2242
EP - 2230-2242
PB - Wiley - Verlag Chemie
SN - 2192-6506
KW - DFT calculations
KW - dyes
KW - pigments
KW - photochemistry
KW - reaction mechanisms
KW - spectroscopy
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202000370
N2 - 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.
ER -
MARTÍNEK, Marek, Jiri VANA, Peter ŠEBEJ, Rafael NAVRATIL, Tomáš SLANINA, Lucie LUDVÍKOVÁ, Jana ROITHOVÁ a Petr KLÁN. Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts. \textit{ChemPlusChem}. Weinheim: Wiley - Verlag Chemie, 2020, roč.~85, č.~10, s.~2230-2242. ISSN~2192-6506. Dostupné z: https://dx.doi.org/10.1002/cplu.202000370.
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