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

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

66 Scopus citations

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. © 2014 the Partner Organisations.

Original language	English (US)
Pages (from-to)	1908
Journal	Chemical Science
Volume	5
Issue number	5
DOIs	https://doi.org/10.1039/c3sc53015a
State	Published - 2014

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1039/c3sc53015a

Cite this

@article{75ba0c13297d4c3786d34755acdcf516,

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. {\textcopyright} 2014 the Partner Organisations.",

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

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The work was supported by a A*STAR BMRC grant (10/1/21/19/642), a MOE Tier 2 grant (MOE2011-T2-2-130) and IMRE Core funding (IMRE/13-1C0205).",

year = "2014",

doi = "10.1039/c3sc53015a",

language = "English (US)",

volume = "5",

pages = "1908",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "5",

}

TY - JOUR

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

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The work was supported by a A*STAR BMRC grant (10/1/21/19/642), a MOE Tier 2 grant (MOE2011-T2-2-130) and IMRE Core funding (IMRE/13-1C0205).

PY - 2014

Y1 - 2014

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. © 2014 the Partner Organisations.

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. © 2014 the Partner Organisations.

UR - http://hdl.handle.net/10754/563189

UR - http://xlink.rsc.org/?DOI=c3sc53015a

UR - http://www.scopus.com/inward/record.url?scp=84898074509&partnerID=8YFLogxK

U2 - 10.1039/c3sc53015a

DO - 10.1039/c3sc53015a

M3 - Article

SN - 2041-6520

VL - 5

SP - 1908

JO - Chemical Science

JF - Chemical Science

IS - 5

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this