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Mono- and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis-1,4-([3]Cumulene)-p-carboquinoid System.
Barry, Brian M; Soper, R Graeme; Hurmalainen, Juha; Mansikkamäki, Akseli; Robertson, Katherine N; McClennan, William L; Veinot, Alex J; Roemmele, Tracey L; Werner-Zwanziger, Ulrike; Boeré, René T; Tuononen, Heikki M; Clyburne, Jason A C; Masuda, Jason D.
Afiliação
  • Barry BM; Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3, Canada.
  • Soper RG; Department of Chemistry, University of Wisconsin-Platteville, Platteville, WI 5, 3818-3099, USA.
  • Hurmalainen J; Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3, Canada.
  • Mansikkamäki A; Department of Chemistry, Nanoscience Centre, University of Jyväskylä, P.O Box 35, University of Jyväskylä, FI-40014, Finland.
  • Robertson KN; Department of Chemistry, Nanoscience Centre, University of Jyväskylä, P.O Box 35, University of Jyväskylä, FI-40014, Finland.
  • McClennan WL; Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3, Canada.
  • Veinot AJ; Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3, Canada.
  • Roemmele TL; Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3, Canada.
  • Werner-Zwanziger U; Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, T1K 3M4, Canada.
  • Boeré RT; Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3, Canada.
  • Tuononen HM; Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, T1K 3M4, Canada.
  • Clyburne JAC; Department of Chemistry, Nanoscience Centre, University of Jyväskylä, P.O Box 35, University of Jyväskylä, FI-40014, Finland.
  • Masuda JD; Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3, Canada.
Angew Chem Int Ed Engl ; 57(3): 749-754, 2018 01 15.
Artigo em Inglês | MEDLINE | ID: mdl-29152832
ABSTRACT
An extended π-system containing two [3]cumulene fragments separated by a p-carboquinoid and stabilized by two capping N-heterocyclic carbenes (NHCs) has been prepared. Mono- and bis(imidazolidinium ethynyl) cations have also been synthesized from the reaction of an NHC with phenylethynyl bromide or 1,4-bis(bromoethynyl)benzene. Cyclic voltammetry coupled with synthetic and structural studies showed that the dication is readily reduced to a neutral, singlet bis-1,4-([3]cumulene)-p-carboquinoid as a result of the π-accepting properties of the capping NHCs.

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Texto completo: Disponível Coleções: Bases de dados internacionais Base de dados: MEDLINE Idioma: Inglês Revista: Angew Chem Int Ed Engl Ano de publicação: 2018 Tipo de documento: Artigo País de afiliação: Canadá