Synthesis and properties of push-pull imidazole derivatives with application as photoredox catalysts
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Synthesis and properties of push-pull imidazole derivatives with application as photoredox catalysts
Original language description
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.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ARKIVOC
ISSN
1551-7004
e-ISSN
—
Volume of the periodical
2017
Issue of the periodical within the volume
4
Country of publishing house
US - UNITED STATES
Number of pages
13
Pages from-to
330-342
UT code for WoS article
000414746900027
EID of the result in the Scopus database
—