Super-heptazethrene

Handle URI:
http://hdl.handle.net/10754/623144
Title:
Super-heptazethrene
Authors:
Zeng, Wangdong; Sun, Zhe; Herng, Tun Seng; Goncalves, Theo; Gopalakrishna, Tullimilli Y.; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Ding, Jun; Wu, Jishan
Abstract:
The challenging synthesis of a laterally extended heptazethrene molecule, the super-heptazethrene derivative SHZ-CF3, is reported. This molecule was prepared using a strategy involving a multiple selective intramolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. Compound SHZ-CF3 exhibits an open-shell singlet diradical ground state with a much larger diradical character compared with the heptazethrene derivatives. An intermediate dibenzo-terrylene SHZ-2H was also obtained during the synthesis. This study provides a new synthetic method to access large-size quinoidal polycyclic hydrocarbons with unique physical properties.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division
Citation:
Zeng W, Sun Z, Herng TS, Gonçalves TP, Gopalakrishna TY, et al. (2016) Super-heptazethrene. Angewandte Chemie International Edition 55: 8615–8619. Available: http://dx.doi.org/10.1002/anie.201602997.
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
30-May-2016
DOI:
10.1002/anie.201602997; 10.1002/ange.201602997
Type:
Article
ISSN:
1433-7851
Sponsors:
This work was supported by the MOE Tier 3 programme (MOE2014-T3-1-004) and by an A*STAR JCO grant (1431AFG100). We thank Dr. Hiroyasu Sato in Rigaku Co. and Dr. Bruno Donnadieu in NUS for the crystallographic analysis.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorZeng, Wangdongen
dc.contributor.authorSun, Zheen
dc.contributor.authorHerng, Tun Sengen
dc.contributor.authorGoncalves, Theoen
dc.contributor.authorGopalakrishna, Tullimilli Y.en
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorDing, Junen
dc.contributor.authorWu, Jishanen
dc.date.accessioned2017-04-13T11:50:57Z-
dc.date.available2017-04-13T11:50:57Z-
dc.date.issued2016-05-30en
dc.identifier.citationZeng W, Sun Z, Herng TS, Gonçalves TP, Gopalakrishna TY, et al. (2016) Super-heptazethrene. Angewandte Chemie International Edition 55: 8615–8619. Available: http://dx.doi.org/10.1002/anie.201602997.en
dc.identifier.issn1433-7851en
dc.identifier.doi10.1002/anie.201602997en
dc.identifier.doi10.1002/ange.201602997en
dc.identifier.urihttp://hdl.handle.net/10754/623144-
dc.description.abstractThe challenging synthesis of a laterally extended heptazethrene molecule, the super-heptazethrene derivative SHZ-CF3, is reported. This molecule was prepared using a strategy involving a multiple selective intramolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. Compound SHZ-CF3 exhibits an open-shell singlet diradical ground state with a much larger diradical character compared with the heptazethrene derivatives. An intermediate dibenzo-terrylene SHZ-2H was also obtained during the synthesis. This study provides a new synthetic method to access large-size quinoidal polycyclic hydrocarbons with unique physical properties.en
dc.description.sponsorshipThis work was supported by the MOE Tier 3 programme (MOE2014-T3-1-004) and by an A*STAR JCO grant (1431AFG100). We thank Dr. Hiroyasu Sato in Rigaku Co. and Dr. Bruno Donnadieu in NUS for the crystallographic analysis.en
dc.publisherWiley-Blackwellen
dc.subjectpolycyclic hydrocarbonsen
dc.subjectquinoidsen
dc.subjectradicalsen
dc.subjectsynthetic methodsen
dc.subjectzethreneen
dc.titleSuper-heptazethreneen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionDepartment of Chemistry; National University of Singapore; 3 Science Drive 3 117543 Singapore Singaporeen
dc.contributor.institutionDepartment of Materials Science and Engineering; National University of Singapore; 119260 Singapore Singaporeen
dc.contributor.institutionInstitute of Materials Research and Engineering, A*STAR; 2 Fusionopolis Way, Innovis, #08-03 117602 Singapore Singaporeen
kaust.authorGoncalves, Theoen
kaust.authorHuang, Kuo-Weien
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