Synthesis and electronic properties of a linearly fused anthracene dimer

Evans O. Onyango, Philip Z. Mannes, Alexandre Pletnev, Devin B. Granger, Qianxiang Ai, Chad Risko, John E. Anthony, Gordon W. Gribble

Research output: Contribution to journalArticlepeer-review

Abstract

We describe the synthesis and electronic properties of the novel interrupted hexacene 5,16-diphenylcyclobuta[1,2-b:3,4-b′]dianthracene (1). The synthesis is rooted in a sequential twin Sonogashira coupling of 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene followed by a Vollhardt 2+2+2 cyclotrimerization to give o-bromoaryl(trimethylsilyl) 8, after selective bromination. A Diels-Alder cycloaddition of the aryne from 8 and 1,3-diphenylisobenzofuran gave 1 after deoxygenation. Photophysical studies suggest that the fused cyclobutane ring been the two anthracene rings allows through-conjugation, but does not allow 1 to behave as a conjugated acene. Attempts to synthesize the parent analogue, cyclobuta[1,2-b:3,4-b′]dianthracene (2) were not successful, but detailed calculations are reported for both 1 and 2.

Original languageEnglish
Article number152182
JournalTetrahedron Letters
Volume61
Issue number31
DOIs
StatePublished - Jul 30 2020

Bibliographical note

Funding Information:
GWG acknowledges support by the donors of the Petroleum Research Fund administered by the American Chemical Society. PZM thanks Dartmouth College for a Zabriskie Fellowship.

Funding Information:
GWG acknowledges support by the donors of the Petroleum Research Fund administered by the American Chemical Society . PZM thanks Dartmouth College for a Zabriskie Fellowship.

Publisher Copyright:
© 2020 Elsevier Ltd

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Keywords

  • Anthracene
  • DFT calculations
  • Diels-Alder cycloaddition
  • Fused cyclobutanes
  • Photophysical studies
  • Polycyclic aromatic hydrocarbons
  • UV/Vis absorption

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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