Phenanthroline-Fused Pyrazinacenes: One-Pot Synthesis, Tautomerization and a RuII(2,2′-bpy)2 Derivative

Pavel Švec, Whitney A. Webre, Gary J. Richards, Jan Labuta, Yutaka Wakayama, David Miklík, Paul A. Karr, Toshiyuki Mori, Katsuhiko Ariga, Francis D'Souza, Jonathan P. Hill

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2541-2548
Number of pages8
JournalEuropean Journal of Inorganic Chemistry
Volume2018
Issue number22
DOIs
Publication statusPublished - 2018 Jun 15
Externally publishedYes

Keywords

  • Dye-sensitized solar cells
  • Heteroacene
  • Phenanthroline
  • Pyrazinacene
  • Tautomerization

ASJC Scopus subject areas

  • Inorganic Chemistry

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