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Liu J, Ravat P, Wagner M, et al. Tetrabenzo[a,f,j,o]perylene: a polycyclic aromatic hydrocarbon with an open-shell singlet biradical ground state. Angew Chem Int Ed Engl. 2015;54(42):12442-6doi: 10.1002/anie.201502657.
Liu, J., Ravat, P., Wagner, M., Baumgarten, M., Feng, X., & Müllen, K. (2015). Tetrabenzo[a,f,j,o]perylene: a polycyclic aromatic hydrocarbon with an open-shell singlet biradical ground state. Angewandte Chemie (International ed. in English), 54(42), 12442-6. https://doi.org/10.1002/anie.201502657
Liu, Junzhi, et al. "Tetrabenzo[a,f,j,o]perylene: a polycyclic aromatic hydrocarbon with an open-shell singlet biradical ground state." Angewandte Chemie (International ed. in English) vol. 54,42 (2015): 12442-6. doi: https://doi.org/10.1002/anie.201502657
Liu J, Ravat P, Wagner M, Baumgarten M, Feng X, Müllen K. Tetrabenzo[a,f,j,o]perylene: a polycyclic aromatic hydrocarbon with an open-shell singlet biradical ground state. Angew Chem Int Ed Engl. 2015 Oct 12;54(42):12442-6. doi: 10.1002/anie.201502657. Epub 2015 Jun 12. PMID: 26073193.
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Angew Chem Int Ed Engl. 2015 Oct 12;54(42):12442-6. doi: 10.1002/anie.201502657. Epub 2015 Jun 12.

Tetrabenzo[a,f,j,o]perylene: a polycyclic aromatic hydrocarbon with an open-shell singlet biradical ground state.

Angewandte Chemie (International ed. in English)

Junzhi Liu, Prince Ravat, Manfred Wagner, Martin Baumgarten, Xinliang Feng, Klaus Müllen

Affiliations

  1. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany).
  2. Center for Advancing Electronics Dresden (cfaed) and Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden (Germany). [email protected].
  3. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany). [email protected].

PMID: 26073193 DOI: 10.1002/anie.201502657

Abstract

A novel tetrabenzo[a,f,j,o]perylene, namely "bistetracene" in which two tetracenes are connected side by side with two bonds, was synthesized and characterized. An optical energy gap of about 1.56 eV is derived from the UV/Vis absorption spectrum, showing the low optical gap feature of such zigzag-edged polycyclic aromatic hydrocarbons (PAHs). Theoretical calculations and physical property investigations manifest that such a PAH possesses a prominent biradical character in the ground state, which is the first example among bistetracene derivatives. However, the bistetracene can easily undergo oxidation to tetrabenzo[a,f,j,o]perylene-9,19-dione (diketone) under ambient conditions. Thereby, such zigzag-edged PAH provides insight into understanding the edge state of other expanded homologues, such as peri-tetracenes or peri-pentacenes.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: biradical; bistetracene; perylenes; polycyclic arenes; zigzag-edge

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