Issue 5, 2014
From the journal:

Chemical Science

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

Yuan Li,a   Kuo-Wei Huang,b   Zhe Sun,a   Richard D. Webster,c   Zebing Zeng,a   Wangdong Zeng,a   Chunyan Chi,a   Ko Furukawa*d  and  Jishan Wu*ae  

* Corresponding authors

a Department of Chemistry, National University of Singapore, Science Drive 3, Singapore
E-mail: chmwuj@nus.edu.sg
Fax: +65-67791691
Tel: +65-65162677

b King Abdullah University of Science and Technology (KAUST), Division of Physical Sciences and Engineering and KAUST Catalysis Center, Thuwal 23955-6900, Saudi Arabia

c Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore

d Center for Instrumental Analysis, Institute for Research Promotion, Niigata University, 8050 Ikarashi 2-no-sho, Nishi-ku, Niigta 950-2181, Japan
E-mail: kou-f@chem.sc.niigata-u.ac.jp

e Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore

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.

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

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Article information

DOI
https://doi.org/10.1039/C3SC53015A
Article type
Edge Article
Submitted
31 Oct 2013
Accepted
30 Jan 2014
First published
30 Jan 2014

Chem. Sci., 2014,5, 1908-1914

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

Y. Li, K. Huang, Z. Sun, R. D. Webster, Z. Zeng, W. Zeng, C. Chi, K. Furukawa and J. Wu, Chem. Sci., 2014, 5, 1908 DOI: 10.1039/C3SC53015A

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