J
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.
Základní údaje
Originální název
Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts
Autoři
MARTÍNEK, Marek (203 Česká republika, domácí), Jiri VANA (203 Česká republika), Peter ŠEBEJ (703 Slovensko, domácí), Rafael NAVRATIL (203 Česká republika), Tomáš SLANINA (203 Česká republika, domácí), Lucie LUDVÍKOVÁ (203 Česká republika, domácí), Jana ROITHOVÁ (203 Česká republika) a Petr KLÁN (203 Česká republika, garant, domácí)
Vydání
ChemPlusChem, Weinheim, Wiley - Verlag Chemie, 2020, 2192-6506
Další údaje
Typ výsledku
Článek v odborném periodiku
Utajení
není předmětem státního či obchodního tajemství
Kód RIV
RIV/00216224:14310/20:00114563
Organizace
Přírodovědecká fakulta – Masarykova univerzita – Repozitář
Klíčová slova anglicky
DFT calculations; dyes; pigments; photochemistry; reaction mechanisms; spectroscopy
Návaznosti
EF17_043/0009632, projekt VaV. GA18-12477S, projekt VaV. LM2018121, projekt VaV. 857560, interní kód Repo.
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.
Zobrazeno: 20. 10. 2024 09:45