Univerzita PardubiceFakulta chemicko- technologická

Univerzita Pardubice

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Publikace detail

Versatility, tunability and applicability of X-shaped push-pull pyrazine derivatives

Autoři: Bureš Filip

Rok: 2014

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
eng	Versatility, tunability and applicability of X-shaped push-pull pyrazine derivatives	Nowadays, functionalized organic ‐conjugated molecules are tremendously investigated due to their prospective applications as active materials in various optoelectronic devices such as OLEDs, OPVCs, DSSCs or OFETs. A ‐system end‐capped with electron donors and acceptors constitutes a class of organic compounds called push‐pull systems (charge‐transfer (CT) molecules). Such molecules possess plenty of interesting and useful properties such as dipolar character, color, electrochemical activity, solvatochromic behavior, biological activity, nonlinear optical properties etc. In 2012, we have investigated X‐shaped pushpull molecules based on N,N‐dimethylamino donor 5,6‐disubstituted pyrazine‐2,3‐dicarbonitrile. These molecules proved to be tunable and very efficient NLOphores. Based on the recent successful application of Ru, Ir and Pt‐derived MLCT complexes in photoredox chemistry and beside the aforementioned prominent applications of organic X‐shaped CT‐molecules in optoelectronic, we have recently envisaged an utilization of push‐pull molecules 2 as photoredox catalysts. Hence, upon structural tuning we have developed very efficient photoredox catalyst based on dicyanopyrazine which was able to catalyze a broad palette of organic transformations. The catalyzed reactions involve formation of C‐C, C‐H, C‐P and C=O bonds while the high photoredox activity of pyrazine catalyst has been demonstrated in more than eleven reactions. The amount of catalyst in most reactions is less than 0.1 and even 0.01 mol%, representing the lowest catalyst loading in the current photoredox catalysis. Most importantly, an unprecedented asymmetric oxidative olefination of tetrahydroisoquinolines with acryaldehyde has been addressed by utilizing 0.05 mol% of the catalyst and achieving excellent enantioselectivities 81‐91 %.	push-pull systems, pyrazine‐2,3‐dicarbonitrile, NLOphores, photoredox catalysis