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

doi:10.1002/anie.201507039

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 journal › Article › peer-review

60 Scopus citations

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 language	English
Pages (from-to)	13980-13984
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	47
DOIs	https://doi.org/10.1002/anie.201507039
State	Published - 16 Nov 2015

Keywords

biradicals
dyes
perylene bisimides
pigments
radicals

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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.",

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T2 - Synthesis and Molecular Properties

AU - Schmidt, David

AU - Son, Minjung

AU - Lim, Jong Min

AU - Lin, Mei Jin

AU - Krummenacher, Ivo

AU - Braunschweig, Holger

AU - Kim, Dongho

AU - Würthner, Frank

PY - 2015/11/16

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AB - 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.

KW - biradicals

KW - dyes

KW - perylene bisimides

KW - pigments

KW - radicals

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JO - Angewandte Chemie - International Edition

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Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties

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