Katalytická fotooxidace 4-methoxybenzylalkoholu pomocí komplexu flavin-Zn(II)-cyklen

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F04%3A00011377" target="_blank" >RIV/60461373:22310/04:00011377 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Catalytic Photooxidation of 4-Methoxybenzyl alcohol with Flavin Zinc(II) cyclen complex

Popis výsledku v původním jazyce

Flavin-zinc(II)-cyclen 10 contains a substrate binding site (zinc(II)-cyclen) and a chromophore (flavin) covalently linked. Upon irradiation compound 10 effectively oxidizes 4-methoxybenzyl alcohol 11-CH3 to the corresponding benzaldehyde in water and inacetonitrile. In the presence of air the reduced flavin 10-H2 is reoxidized and catalytic amounts of 10 are sufficient for alcohol conversion. The mechanism of oxidation is based on photoinduced electron-transfer from coordinated benzyl alcohol to the flavin chromophore. This intramolecular process leads to a much higher efficiency of the photooxidation with 30-fold higher quantum yields than the comparable intermolecular process of a flavin chromophore without binding site. For the reaction in buffered aqueous solution a quantum yield of F = 0.4 is observed. The turnover number in acetonitrile solution is increased by high benzyl alcohol concentration up to 20. The results show, that the covalent combination of a chromophore and a sui

Název v anglickém jazyce

Catalytic Photooxidation of 4-Methoxybenzyl alcohol with Flavin Zinc(II) cyclen complex

Popis výsledku anglicky

Flavin-zinc(II)-cyclen 10 contains a substrate binding site (zinc(II)-cyclen) and a chromophore (flavin) covalently linked. Upon irradiation compound 10 effectively oxidizes 4-methoxybenzyl alcohol 11-CH3 to the corresponding benzaldehyde in water and inacetonitrile. In the presence of air the reduced flavin 10-H2 is reoxidized and catalytic amounts of 10 are sufficient for alcohol conversion. The mechanism of oxidation is based on photoinduced electron-transfer from coordinated benzyl alcohol to the flavin chromophore. This intramolecular process leads to a much higher efficiency of the photooxidation with 30-fold higher quantum yields than the comparable intermolecular process of a flavin chromophore without binding site. For the reaction in buffered aqueous solution a quantum yield of F = 0.4 is observed. The turnover number in acetonitrile solution is increased by high benzyl alcohol concentration up to 20. The results show, that the covalent combination of a chromophore and a sui

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2004

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemistry A European Journal

ISSN

0947-6539

e-ISSN

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Svazek periodika

10

Číslo periodika v rámci svazku

24

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

6223-6231

Kód UT WoS článku

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EID výsledku v databázi Scopus

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