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Phenanthroline-Fused Pyrazinacenes: One-Pot Synthesis, Tautomerization and a Ru-II(2,2-bpy)(2) Derivative
Authors: Svec Pavel | Webre Whitney A. | Richards Gary J. | Labuta Jan | Wakayama Yutaka | Miklík David | Karr Paul A. | Mori Toshiyuki | Ariga Katsuhiko | D'Souza Francis | Hill Jonathan P.
Year: 2018
Type of publication: článek v odborném periodiku
Name of source: European Journal of Inorganic Chemistry
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 2541-2548
Titles:
Language Name Abstract Keywords
cze Fenantrolinem kondenzované pyrazinaceny: one-pot syntéza, tautomerie a Ru-II(2,2-bpy)(2) deriváty Je popsána one-pot syntéza pyrazinů kondenzovaných s fenantrolinem a jejich alkylace vedoucí ke zvýšení rozpustnosti. Tautomerie výchozího pyrazinacenu vede ke směsi izomerů, byly zohledněny faktory ovlivňující relativní výtěžky těchto izomerů. Zastoupení izomerů může být popsáno dvoustupňovým reakčním modelem. heteroacen; pyrazinacen; tautomerie; fenantrolin
eng Phenanthroline-Fused Pyrazinacenes: One-Pot Synthesis, Tautomerization and a Ru-II(2,2-bpy)(2) Derivative We report the one-pot synthesis of a phenanthroline-fused pyrazinacene derivative (6,13-dihydrodipyrido[3,2-a:2,3-c]-5,6,7,8,11,12,13,14-octaazapentacene-9,10-dicarbonitrile) and its behaviour under alkylating conditions used to improve solubility. Tautomerization of the starting pyrazinacene due to the presence of a reduced pyrazine ring contained within an octaazatetracene chromophore led to mixtures of isomers, and factors affecting the relative yields of these isomers were considered. Isomer population can be described by a two-step reaction model where initial N-alkylation affects the reactivity of the remaining nitrogen atoms available for subsequent alkylation. A discrete soluble non-isomerizable phenanthroline-fused pyrazinacene was also prepared and the activity of its Ru(bpy)(2) complex as a photosensitizer for dye-sensitized solar cell application was investigated. The compounds reported illustrate the unusual reactivity of reduced pyrazinacenes and also their potential as photosensitizers. Heteroacene; Pyrazinacene; Tautomerization; Phenanthroline; Dye-sensitized solar cells

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