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@article{1671638, author = {Russo, Marina and Štacko, Peter and Nachtigallová, Dana and Klán, Petr}, article_location = {Washington, D.C.}, article_number = {5}, doi = {http://dx.doi.org/10.1021/acs.joc.9b03248}, keywords = {Quantum yield; Alcohols; Oxygen; Inorganic carbon compounds; Irradiation}, language = {eng}, issn = {0022-3263}, journal = {Journal of Organic Chemistry}, note = {CZ.02.1.01/0.0/0.0/18_046/0015975 neuplatňovat. Místo toho uplatnit EF17_043/0009632.}, title = {Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms}, url = {https://pubs.acs.org/doi/10.1021/acs.joc.9b03248}, volume = {85}, year = {2020} }
TY - JOUR ID - 1671638 AU - Russo, Marina - Štacko, Peter - Nachtigallová, Dana - Klán, Petr PY - 2020 TI - Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms JF - Journal of Organic Chemistry VL - 85 IS - 5 SP - 3527-3537 EP - 3527-3537 PB - American Chemical Society SN - 00223263 N1 - CZ.02.1.01/0.0/0.0/18_046/0015975 neuplatňovat. Místo toho uplatnit EF17_043/0009632. KW - Quantum yield KW - Alcohols KW - Oxygen KW - Inorganic carbon compounds KW - Irradiation UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b03248 L2 - https://pubs.acs.org/doi/10.1021/acs.joc.9b03248 N2 - Carbon monoxide is a naturally occurring gasotransmitter combining inherent toxicity with a remarkable therapeutic potential and arduous administration. Photoactivatable carbon monoxide-releasing molecules (photoCORMs) are chemical agents that allow for precise spatial and temporal control over the CO release. In this work, we present a comprehensive mechanistic study of the photochemical CO release from 3-hydroxy-2-phenyl-4H-chromen-4-one, a pi-extended 3-hydroxyflavone photoCORM, in methanol using steady-state and transient absorption spectroscopies and quantum chemical calculations. The multiplicity of the productive excited states and the role of oxygen (O-2) in the CO production are emphasized, revealing a photoreaction dichotomy of the 3-hydroxyflavone acid and base forms. The utilization of three major orthogonal mechanistic pathways, all of which lead to the CO release, can fuel future endeavors to improve the CO release efficacy of 3-hydroxyflavone-based derivatives and refine their potential medical applications as photoCORMs. ER -
RUSSO, Marina, Peter ŠTACKO, Dana NACHTIGALLOVÁ a Petr KLÁN. Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms. \textit{Journal of Organic Chemistry}. Washington, D.C.: American Chemical Society, 2020, roč.~85, č.~5, s.~3527-3537. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/acs.joc.9b03248.
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