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

J. Wilbuer; D. C. Grenz; G. Schnakenburg; B. Esser

doi:10.1039/C6QO00487C

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

J. Wilbuer,^ab D. C. Grenz,^a G. Schnakenburg^c and B. Esser

*^a

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^a Institute for Organic Chemistry, University of Freiburg, Albertstr. 21, 79104 Freiburg, Germany
E-mail: besser@oc.uni-freiburg.de

^b Kekulé-Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany

^c Institute for Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany

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.

This article is part of the themed collection: Novel π-electron molecular scaffolds

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DOI: https://doi.org/10.1039/C6QO00487C
Article type: Research Article
Submitted: 24 Aug 2016
Accepted: 26 Sep 2016
First published: 27 Sep 2016
This article is Open Access

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Org. Chem. Front., 2017,4, 658-663

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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, 4, 658 DOI: 10.1039/C6QO00487C

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

Abstract

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

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