Jump to main content
Jump to site search


Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap

Author affiliations

Abstract

Dibenzo[a,e]pentalene (DBP) is a low-bandgap organic semiconductor. A versatile synthetic route to DBPs substituted with aryl or alkyl groups in the 5,10-positions and electron-donating or -accepting functionalities in the 2,7-positions is described. Six donor- or acceptor-functionalized DBP derivatives were synthesized that show amphoteric redox behavior and band gaps around 2 eV. Through choice of the 2,7-substituents, the HOMO/LUMO energy levels and band gaps can be adjusted within a range of up to 0.6 eV. In the solid state, the DBP derivatives assume herringbone-type packing structures.

Graphical abstract: Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 24 Aug 2016, accepted on 26 Sep 2016 and first published on 27 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00487C
Citation: Org. Chem. Front., 2017, Advance Article
  • Open access: Creative Commons BY license
  •   Request permissions

    Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap

    J. Wilbuer, D. C. Grenz, G. Schnakenburg and B. Esser, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C6QO00487C

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author