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Pentacenones as Divergent Intermediates to Unsymmetrically Substituted Pentacenes: Synthesis and Crystallographic Analysis.
Schroeder, Zachary W; McDonald, Robert; Ferguson, Michael J; Chalifoux, Wesley A; Tykwinski, Rik R; Lehnherr, Dan.
Afiliação
  • Schroeder ZW; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • McDonald R; X-ray Crystallography Lab, Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Ferguson MJ; X-ray Crystallography Lab, Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Chalifoux WA; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Tykwinski RR; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
  • Lehnherr D; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
J Org Chem ; 87(24): 16236-16249, 2022 Dec 16.
Article em En | MEDLINE | ID: mdl-36416781
We report a general method for the desymmetrization of 6,13-pentacenequinone to access ethynylated pentacene ketones, namely, 13-hydroxy-13-(ethynylated)pentacene-6(13H)-ones. These pentacene ketones ("pentacenones") serve as divergent intermediates to unsymmetrically 6,13-disubstituted pentacenes, commonly used for studying singlet fission processes and charge transport phenomena in organic field effect transistors. We report a synthetic method to access pentacenones, which utilizes a precipitation/crystallization from the crude mixture to enable facile purification on a multigram scale. X-ray crystallographic analysis of the pentacenones reveals key noncovalent interactions that contribute to the crystallization, specifically, hydrogen bonding between the ketone and alcohol functional groups as well as π-π-stacking and dipole-dipole interactions.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2022 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2022 Tipo de documento: Article