A kinetically blocked 1,14:11,12-dibenzopentacene: a persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon
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-Kekule polyc...
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| Published in | Chemical science (Cambridge) Vol. 5; no. 5; pp. 1908 - 1914 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
01.01.2014
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| Subjects | |
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| 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-Kekule 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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| AbstractList | 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-Kekule 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 | Li, Yuan Furukawa, Ko Zeng, Zebing Wu, Jishan Huang, Kuo-Wei Sun, Zhe Zeng, Wangdong Chi, Chunyan Webster, Richard D. |
| Author_xml | – sequence: 1 givenname: Yuan surname: Li fullname: Li, Yuan – sequence: 2 givenname: Kuo-Wei surname: Huang fullname: Huang, Kuo-Wei – sequence: 3 givenname: Zhe surname: Sun fullname: Sun, Zhe – sequence: 4 givenname: Richard D. surname: Webster fullname: Webster, Richard D. – sequence: 5 givenname: Zebing surname: Zeng fullname: Zeng, Zebing – sequence: 6 givenname: Wangdong surname: Zeng fullname: Zeng, Wangdong – sequence: 7 givenname: Chunyan surname: Chi fullname: Chi, Chunyan – sequence: 8 givenname: Ko surname: Furukawa fullname: Furukawa, Ko – sequence: 9 givenname: Jishan surname: Wu fullname: Wu, Jishan |
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| Snippet | The synthesis of high-spin polycyclic hydrocarbons is very challenging due to their extremely high reactivity. Herein, we report the synthesis and... |
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| SubjectTerms | Benzenoids Blocking Density functional theory Displays Hydrocarbons Isomers Mathematical analysis Synthesis |
| Title | A kinetically blocked 1,14:11,12-dibenzopentacene: a persistent triplet diradical of a non-Kekulé polycyclic benzenoid hydrocarbon |
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