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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