Mechanisms of Orthogonal Photodecarbonylation Reactions of
3-Hydroxyflavone-Based Acid-Base Forms

J 2020

Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms

RUSSO, Marina, Peter ŠTACKO, Dana NACHTIGALLOVÁ and Petr KLÁN

Basic information

Original name

Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms

Authors

RUSSO, Marina (380 Italy, belonging to the institution), Peter ŠTACKO (703 Slovakia, belonging to the institution), Dana NACHTIGALLOVÁ (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Organic Chemistry, Washington, D.C. American Chemical Society, 2020, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.354

RIV identification code

RIV/00216224:14310/20:00114240

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.9b03248

UT WoS

000518875700060

Keywords in English

Quantum yield; Alcohols; Oxygen; Inorganic carbon compounds; Irradiation

Abstract

V originále

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.

Links

EF17_043/0009632, research and development project

Name: CETOCOEN Excellence

GA18-12477S, research and development project

Name: Fotoaktivace CO a H2S jako plynných signálních molekul pro biologické a medicinální aplikace

Investor: Czech Science Foundation

LM2018121, research and development project

Name: Výzkumná infrastruktura RECETOX (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR, RECETOX RI

Citovat

RUSSO, Marina, Peter ŠTACKO, Dana NACHTIGALLOVÁ and Petr KLÁN. Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms. Journal of Organic Chemistry. Washington, D.C.: American Chemical Society, 2020, vol. 85, No 5, p. 3527-3537. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.9b03248.

@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 and 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, vol.~85, No~5, p.~3527-3537. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.9b03248.

Detailed Information on Publication Record