Synthesis and properties of push-pull imidazole derivatives with application as photoredox catalysts

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F17%3A39910726" target="_blank" >RIV/00216275:25310/17:39910726 - isvavai.cz</a>

Výsledek na webu

<a href="http://www.arkat-usa.org/get-file/60304/" target="_blank" >http://www.arkat-usa.org/get-file/60304/</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3998/ark.5550190.p010.071" target="_blank" >10.3998/ark.5550190.p010.071</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and properties of push-pull imidazole derivatives with application as photoredox catalysts

Popis výsledku v původním jazyce

Two new push-pull molecules with imidazole-4,5-dicarbonitrile acceptor, thiophene and 2-methoxythiophene donors with potential use in photoredox catalysis were designed and prepared. The synthesis started from commercially available imidazole-4,5-dicarbonitrile and its bromination and N-methylation. Subsequent Suzuki-Miyaura cross-coupling with (5-methoxy)thiophene-derived boronic acids afforded target push-pull derivatives. Beside common analytical methods, the molecular structure of 5-methoxythiophen-2-yl derivative has also been verified by X-ray analysis. DSC analyses showed remarkable thermal stabilities of both target derivatives with T-m and T-D values above 150 and 270 degrees C, respectively. Fundamental properties and extent of the intramolecular charge-transfer were further studied by UV-VIS absorption spectra and DFT calculations. Fundamental photoredox properties of target imidazole derivatives were elucidated. Both push-pull molecules were preliminary tested as photoredox catalysts in cross-dehydrogenative coupling reaction between tetrahydroisoquinoline and nitromethane and the results were compared with those obtained by pyrazine2,3-dicarbonitrile-derived catalyst.

Název v anglickém jazyce

Synthesis and properties of push-pull imidazole derivatives with application as photoredox catalysts

Popis výsledku anglicky

Two new push-pull molecules with imidazole-4,5-dicarbonitrile acceptor, thiophene and 2-methoxythiophene donors with potential use in photoredox catalysis were designed and prepared. The synthesis started from commercially available imidazole-4,5-dicarbonitrile and its bromination and N-methylation. Subsequent Suzuki-Miyaura cross-coupling with (5-methoxy)thiophene-derived boronic acids afforded target push-pull derivatives. Beside common analytical methods, the molecular structure of 5-methoxythiophen-2-yl derivative has also been verified by X-ray analysis. DSC analyses showed remarkable thermal stabilities of both target derivatives with T-m and T-D values above 150 and 270 degrees C, respectively. Fundamental properties and extent of the intramolecular charge-transfer were further studied by UV-VIS absorption spectra and DFT calculations. Fundamental photoredox properties of target imidazole derivatives were elucidated. Both push-pull molecules were preliminary tested as photoredox catalysts in cross-dehydrogenative coupling reaction between tetrahydroisoquinoline and nitromethane and the results were compared with those obtained by pyrazine2,3-dicarbonitrile-derived catalyst.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

ARKIVOC

ISSN

1551-7004

e-ISSN

—

Svazek periodika

2017

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

13

Strana od-do

330-342

Kód UT WoS článku

000414746900027

EID výsledku v databázi Scopus

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