Phenanthroline-fused pyrazinacenes: one-pot synthesis, tautomerization and a Ru-II(2,2'-bpy)2 derivative

0490193 - ÚMCH 2019 RIV DE eng J - Článek v odborném periodiku
Švec, Pavel - Webre, W. A. - Richards, G. J. - Labuta, J. - Wakayama, Y. - Miklík, D. - Karr, P. A. - Mori, T. - Ariga, K. - D´Souza, F. - Hill, J. P.
Phenanthroline-fused pyrazinacenes: one-pot synthesis, tautomerization and a Ru-II(2,2'-bpy)2 derivative.
European Journal of Inorganic Chemistry. Roč. 2018, č. 22 (2018), s. 2541-2548. ISSN 1434-1948. E-ISSN 1099-0682
Institucionální podpora: RVO:61389013
Klíčová slova: heteroacene * pyrazinacene * tautomerization
Obor OECD: Polymer science
Impakt faktor: 2.578, rok: 2018

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.
Trvalý link: http://hdl.handle.net/11104/0284830