Detailed Information on Publication Record
2020
Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts
MARTÍNEK, Marek, Jiri VANA, Peter ŠEBEJ, Rafael NAVRATIL, Tomáš SLANINA et. al.Basic information
Original name
Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts
Authors
MARTÍNEK, Marek (203 Czech Republic, belonging to the institution), Jiri VANA (203 Czech Republic), Peter ŠEBEJ (703 Slovakia, belonging to the institution), Rafael NAVRATIL (203 Czech Republic), Tomáš SLANINA (203 Czech Republic, belonging to the institution), Lucie LUDVÍKOVÁ (203 Czech Republic, belonging to the institution), Jana ROITHOVÁ (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)
Edition
ChemPlusChem, Weinheim, Wiley - Verlag Chemie, 2020, 2192-6506
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Country of publisher
Germany
Confidentiality degree
není předmětem státního či obchodního tajemství
References:
RIV identification code
RIV/00216224:14310/20:00114563
Organization
Přírodovědecká fakulta – Repository – Repository
UT WoS
000553597000001
Keywords in English
DFT calculations; dyes; pigments; photochemistry; reaction mechanisms; spectroscopy
Links
EF17_043/0009632, research and development project. GA18-12477S, research and development project. LM2018121, research and development project. 857560, interní kód Repo.
Změněno: 18/2/2023 04:47, RNDr. Daniel Jakubík
Abstract
V originále
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.