A kinetically blocked 1,14:11,12-dibenzopentacene: A persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon

Yuan Li; Kuo Wei Huang; Zhe Sun; Richard D. Webster; Zebing Zeng; Wangdong Zeng; Chunyan Chi; Ko Furukawa; Jishan Wu

doi:10.1039/c3sc53015a

A kinetically blocked 1,14:11,12-dibenzopentacene: A persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon

Yuan Li, Kuo Wei Huang, Zhe Sun, Richard D. Webster, Zebing Zeng, Wangdong Zeng, Chunyan Chi, Ko Furukawa^*, Jishan Wu

^*Corresponding author for this work

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

73 Citations (Scopus)

Abstract

The synthesis of high-spin polycyclic hydrocarbons is very challenging due to their extremely high reactivity. Herein, we report the synthesis and characterization of a kinetically blocked 1,14:11,12-dibenzopentacene, DP-Mes, which represents a rare persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon. In contrast to its structural isomer 1,14:7,8-dibenzopentacene (heptazethrene) with a singlet biradical ground state, DP-Mes is a triplet diradical as confirmed by ESR and ESTN measurements and density functional theory calculations. DP-Mes also displays intermolecular antiferromagnetic spin interactions in solution at low temperature.

Original language	English
Pages (from-to)	1908-1914
Number of pages	7
Journal	Chemical Science
Volume	5
Issue number	5
DOIs	https://doi.org/10.1039/c3sc53015a
Publication status	Published - May 2014
Externally published	Yes

ASJC Scopus Subject Areas

General Chemistry

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title = "A kinetically blocked 1,14:11,12-dibenzopentacene: A persistent triplet diradical of a non-Kekul{\'e} polycyclic benzenoid hydrocarbon",

abstract = "The synthesis of high-spin polycyclic hydrocarbons is very challenging due to their extremely high reactivity. Herein, we report the synthesis and characterization of a kinetically blocked 1,14:11,12-dibenzopentacene, DP-Mes, which represents a rare persistent triplet diradical of a non-Kekul{\'e} polycyclic benzenoid hydrocarbon. In contrast to its structural isomer 1,14:7,8-dibenzopentacene (heptazethrene) with a singlet biradical ground state, DP-Mes is a triplet diradical as confirmed by ESR and ESTN measurements and density functional theory calculations. DP-Mes also displays intermolecular antiferromagnetic spin interactions in solution at low temperature.",

author = "Yuan Li and Huang, {Kuo Wei} and Zhe Sun and Webster, {Richard D.} and Zebing Zeng and Wangdong Zeng and Chunyan Chi and Ko Furukawa and Jishan Wu",

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doi = "10.1039/c3sc53015a",

language = "English",

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T1 - A kinetically blocked 1,14:11,12-dibenzopentacene

T2 - A persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon

AU - Li, Yuan

AU - Huang, Kuo Wei

AU - Sun, Zhe

AU - Webster, Richard D.

AU - Zeng, Zebing

AU - Zeng, Wangdong

AU - Chi, Chunyan

AU - Furukawa, Ko

AU - Wu, Jishan

PY - 2014/5

Y1 - 2014/5

N2 - The synthesis of high-spin polycyclic hydrocarbons is very challenging due to their extremely high reactivity. Herein, we report the synthesis and characterization of a kinetically blocked 1,14:11,12-dibenzopentacene, DP-Mes, which represents a rare persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon. In contrast to its structural isomer 1,14:7,8-dibenzopentacene (heptazethrene) with a singlet biradical ground state, DP-Mes is a triplet diradical as confirmed by ESR and ESTN measurements and density functional theory calculations. DP-Mes also displays intermolecular antiferromagnetic spin interactions in solution at low temperature.

AB - The synthesis of high-spin polycyclic hydrocarbons is very challenging due to their extremely high reactivity. Herein, we report the synthesis and characterization of a kinetically blocked 1,14:11,12-dibenzopentacene, DP-Mes, which represents a rare persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon. In contrast to its structural isomer 1,14:7,8-dibenzopentacene (heptazethrene) with a singlet biradical ground state, DP-Mes is a triplet diradical as confirmed by ESR and ESTN measurements and density functional theory calculations. DP-Mes also displays intermolecular antiferromagnetic spin interactions in solution at low temperature.

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DO - 10.1039/c3sc53015a

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A kinetically blocked 1,14:11,12-dibenzopentacene: A persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon

Abstract

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