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Push-pull dicyanoimidazoles in photoredox catalysis

Authors: Ludwig Miroslav | Hloušková Zuzana | Bureš Filip

Year: 2018

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Push-pull dicyanoimidazoles in photoredox catalysis	Photoredox catalysis currently represent a renascent synthetic tool allowing conversion of the solar energy to energy of a chemical bond. Based on our recently developed X shaped dicyanopyrazine organic photoredox catalyst, we focused herein on utilization of five-membered imidazole for construction of Y-shaped push-pull molecules with tailored photoredox properties. Hence, two new push-pull molecules with imidazole-4,5-dicarbonitrile acceptor (dicyanoimidazole, DCI), 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 gradual bromination, methylation and final Suzuki-Miyaura cross-coupling reactions. The fundamental properties of target molecules were studied by available analytical methods including X-ray analysis and DSC. The extent of the intramolecular charge-transfer were further investigated by UV-VIS absorption spectra and DFT calculations. Both push-pull molecules were tested as photoredox catalysts in cross-dehydrogenative coupling reaction between tetrahydroisoquinoline and nitromethane and the results were compared with previously obtained results. Fundamental structure-property-catalytic activity relationships were elucidated.	imidazole-4,5-dicarbonitrile; photoredox catalysis; push-pull molecules