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

University of Würzburg
Yonsei University

Research output: Contribution to journal › Article › peer-review

69 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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10.1002/anie.201507039

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title = "Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties",

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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T1 - Perylene Bisimide Radicals and Biradicals

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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N2 - 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.

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

UR - https://www.scopus.com/pages/publications/84955211873

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DO - 10.1002/anie.201507039

M3 - Article

AN - SCOPUS:84955211873

SN - 1433-7851

VL - 54

SP - 13980

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 47

ER -

Perylene Bisimide Radicals and Biradicals: Synthesis and Molecular Properties

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