Azulene‐Fused Acenes
Non‐alternant non‐benzenoid π‐conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all‐benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene‐fused acene molecules (1, 2 and 3), which are isoelectronic to the...
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| Published in | Angewandte Chemie International Edition Vol. 61; no. 44; pp. e202209286 - n/a |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
02.11.2022
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
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| Abstract | Non‐alternant non‐benzenoid π‐conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all‐benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene‐fused acene molecules (1, 2 and 3), which are isoelectronic to the pentacene, hexacene and heptacene, respectively. X‐ray crystallographic analysis, NMR spectra, and theoretical calculations reveal a localised aromatic backbone comprising all the six‐ and five‐membered rings while the seven‐membered ring remains non‐aromatic. They display properties of both azulene and acenes and are much more stable than the respective acenes. The dications of 1, 2 and 3 were formed by chemical oxidation. Notably, 32+ exhibited an open‐shell diradical character (y0=30.2 %) as confirmed by variable‐temperature NMR and ESR measurements, which can be explained by recovery of aromaticity of an 2,6‐anthraquinodimethane unit annulated with two aromatic tropylium rings.
Fusion of azulene to acenes of various length led to unexpected properties such as aromaticity and photophysical properties, and they are more stable than the respective isoelectronic acenes. Their dications showed aromaticity shift and one of them exhibited open‐shell diradical character. |
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| AbstractList | Non-alternant non-benzenoid pi-conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all-benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene-fused acene molecules (1, 2 and 3), which are isoelectronic to the pentacene, hexacene and heptacene, respectively. X-ray crystallographic analysis, NMR spectra, and theoretical calculations reveal a localised aromatic backbone comprising all the six- and five-membered rings while the seven-membered ring remains non-aromatic. They display properties of both azulene and acenes and are much more stable than the respective acenes. The dications of 1, 2 and 3 were formed by chemical oxidation. Notably, 3(2+) exhibited an open-shell diradical character (y(0)=30.2 %) as confirmed by variable-temperature NMR and ESR measurements, which can be explained by recovery of aromaticity of an 2,6-anthraquinodimethane unit annulated with two aromatic tropylium rings. Non‐alternant non‐benzenoid π‐conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all‐benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene‐fused acene molecules ( 1 , 2 and 3 ), which are isoelectronic to the pentacene, hexacene and heptacene, respectively. X‐ray crystallographic analysis, NMR spectra, and theoretical calculations reveal a localised aromatic backbone comprising all the six‐ and five‐membered rings while the seven‐membered ring remains non‐aromatic. They display properties of both azulene and acenes and are much more stable than the respective acenes. The dications of 1 , 2 and 3 were formed by chemical oxidation. Notably, 3 2+ exhibited an open‐shell diradical character ( y 0 =30.2 %) as confirmed by variable‐temperature NMR and ESR measurements, which can be explained by recovery of aromaticity of an 2,6‐anthraquinodimethane unit annulated with two aromatic tropylium rings. Non-alternant non-benzenoid π-conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all-benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene-fused acene molecules (1, 2 and 3), which are isoelectronic to the pentacene, hexacene and heptacene, respectively. X-ray crystallographic analysis, NMR spectra, and theoretical calculations reveal a localised aromatic backbone comprising all the six- and five-membered rings while the seven-membered ring remains non-aromatic. They display properties of both azulene and acenes and are much more stable than the respective acenes. The dications of 1, 2 and 3 were formed by chemical oxidation. Notably, 32+ exhibited an open-shell diradical character (y0 =30.2 %) as confirmed by variable-temperature NMR and ESR measurements, which can be explained by recovery of aromaticity of an 2,6-anthraquinodimethane unit annulated with two aromatic tropylium rings.Non-alternant non-benzenoid π-conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all-benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene-fused acene molecules (1, 2 and 3), which are isoelectronic to the pentacene, hexacene and heptacene, respectively. X-ray crystallographic analysis, NMR spectra, and theoretical calculations reveal a localised aromatic backbone comprising all the six- and five-membered rings while the seven-membered ring remains non-aromatic. They display properties of both azulene and acenes and are much more stable than the respective acenes. The dications of 1, 2 and 3 were formed by chemical oxidation. Notably, 32+ exhibited an open-shell diradical character (y0 =30.2 %) as confirmed by variable-temperature NMR and ESR measurements, which can be explained by recovery of aromaticity of an 2,6-anthraquinodimethane unit annulated with two aromatic tropylium rings. Non‐alternant non‐benzenoid π‐conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all‐benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene‐fused acene molecules (1, 2 and 3), which are isoelectronic to the pentacene, hexacene and heptacene, respectively. X‐ray crystallographic analysis, NMR spectra, and theoretical calculations reveal a localised aromatic backbone comprising all the six‐ and five‐membered rings while the seven‐membered ring remains non‐aromatic. They display properties of both azulene and acenes and are much more stable than the respective acenes. The dications of 1, 2 and 3 were formed by chemical oxidation. Notably, 32+ exhibited an open‐shell diradical character (y0=30.2 %) as confirmed by variable‐temperature NMR and ESR measurements, which can be explained by recovery of aromaticity of an 2,6‐anthraquinodimethane unit annulated with two aromatic tropylium rings. Fusion of azulene to acenes of various length led to unexpected properties such as aromaticity and photophysical properties, and they are more stable than the respective isoelectronic acenes. Their dications showed aromaticity shift and one of them exhibited open‐shell diradical character. Non‐alternant non‐benzenoid π‐conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all‐benzenoid PHs. Herein, we report the synthesis and physical properties of three azulene‐fused acene molecules (1, 2 and 3), which are isoelectronic to the pentacene, hexacene and heptacene, respectively. X‐ray crystallographic analysis, NMR spectra, and theoretical calculations reveal a localised aromatic backbone comprising all the six‐ and five‐membered rings while the seven‐membered ring remains non‐aromatic. They display properties of both azulene and acenes and are much more stable than the respective acenes. The dications of 1, 2 and 3 were formed by chemical oxidation. Notably, 32+ exhibited an open‐shell diradical character (y0=30.2 %) as confirmed by variable‐temperature NMR and ESR measurements, which can be explained by recovery of aromaticity of an 2,6‐anthraquinodimethane unit annulated with two aromatic tropylium rings. |
| ArticleNumber | 202209286 |
| Author | Han, Yi Ou, Yaping Tao, Tao Huang, Kuo‐Wei Jiang, Qing Ong, Albert Chi, Chunyan |
| Author_xml | – sequence: 1 givenname: Albert orcidid: 0000-0003-2720-6976 surname: Ong fullname: Ong, Albert organization: National University of Singapore – sequence: 2 givenname: Tao surname: Tao fullname: Tao, Tao organization: Nanjing University of Information Science & Technology – sequence: 3 givenname: Qing surname: Jiang fullname: Jiang, Qing email: chmjq@nus.edu.sg organization: National University of Singapore – sequence: 4 givenname: Yi orcidid: 0000-0001-5000-8818 surname: Han fullname: Han, Yi organization: National University of Singapore – sequence: 5 givenname: Yaping surname: Ou fullname: Ou, Yaping organization: National University of Singapore – sequence: 6 givenname: Kuo‐Wei orcidid: 0000-0003-1900-2658 surname: Huang fullname: Huang, Kuo‐Wei organization: King Abdullah University of Science and Technology – sequence: 7 givenname: Chunyan orcidid: 0000-0003-4677-3546 surname: Chi fullname: Chi, Chunyan email: chmcc@nus.edu.sg organization: National University of Singapore |
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| Keywords | DESIGN Aromaticity Polycyclic Hydrocarbon HETEROACENES Azulene MOLECULES CONJUGATED POLYMERS Acene BIAZULENE DIIMIDES PENTACENE BACKBONE DERIVATIVES UNITS |
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| Snippet | Non‐alternant non‐benzenoid π‐conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all‐benzenoid PHs.... Non-alternant non-benzenoid pi-conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all-benzenoid... Non-alternant non-benzenoid π-conjugated polycyclic hydrocarbons (PHs) are expected to exhibit very different electronic properties from the all-benzenoid PHs.... |
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| SubjectTerms | Acene Aromaticity Azulene Chemistry Chemistry, Multidisciplinary Crystallography NMR Nuclear magnetic resonance Oxidation Physical properties Physical Sciences Polycyclic Hydrocarbon Science & Technology |
| Title | Azulene‐Fused Acenes |
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