Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties

David Schmidt, Minjung Son, Jong Min Lim, Mei Jin Lin, Ivo Krummenacher, Holger Braunschweig, Dongho Kim, Frank Würthner

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Unprecedented neutral perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) radicals and biradicals were synthesized by facile chemical oxidation of 4-hydroxyaryl-substituted PBIs. Subsequent characterization by optical and magnetic spectroscopic techniques, as well as quantum chemical calculations, revealed an open-shell singlet biradical ground state for the PBI biradical OS-2. (〈2〉=1.2191) with a relatively small singlet-triplet energy gap of 0.041 eV and a large singlet biradical character of y=0.72.

Original languageEnglish
Pages (from-to)13980-13984
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number47
DOIs
Publication statusPublished - 2015 Nov 16

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Ground state
Energy gap
Oxidation
Acids
perylene bisimide
3,4,9,10-perylene tetracarboxylic acid

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Schmidt, D., Son, M., Lim, J. M., Lin, M. J., Krummenacher, I., Braunschweig, H., ... Würthner, F. (2015). Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties. Angewandte Chemie - International Edition, 54(47), 13980-13984. https://doi.org/10.1002/anie.201507039
Schmidt, David ; Son, Minjung ; Lim, Jong Min ; Lin, Mei Jin ; Krummenacher, Ivo ; Braunschweig, Holger ; Kim, Dongho ; Würthner, Frank. / Perylene Bisimide Radicals and Biradicals : Synthesis and Molecular Properties. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 47. pp. 13980-13984.
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Schmidt, D, Son, M, Lim, JM, Lin, MJ, Krummenacher, I, Braunschweig, H, Kim, D & Würthner, F 2015, 'Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties', Angewandte Chemie - International Edition, vol. 54, no. 47, pp. 13980-13984. https://doi.org/10.1002/anie.201507039

Perylene Bisimide Radicals and Biradicals : Synthesis and Molecular Properties. / Schmidt, David; Son, Minjung; Lim, Jong Min; Lin, Mei Jin; Krummenacher, Ivo; Braunschweig, Holger; Kim, Dongho; Würthner, Frank.

In: Angewandte Chemie - International Edition, Vol. 54, No. 47, 16.11.2015, p. 13980-13984.

Research output: Contribution to journalArticle

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Schmidt D, Son M, Lim JM, Lin MJ, Krummenacher I, Braunschweig H et al. Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties. Angewandte Chemie - International Edition. 2015 Nov 16;54(47):13980-13984. https://doi.org/10.1002/anie.201507039