Super-heptazethrene

Wangdong Zeng; Zhe Sun; Tun Seng Herng; Theo Goncalves; Tullimilli Y. Gopalakrishna; Kuo-Wei Huang; Jun Ding; Jishan Wu

doi:10.1002/anie.201602997

Super-heptazethrene

Wangdong Zeng, Zhe Sun, Tun Seng Herng, Theo Goncalves, Tullimilli Y. Gopalakrishna, Kuo-Wei Huang, Jun Ding, Jishan Wu

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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.

Original language	English (US)
Pages (from-to)	8615-8619
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	30
DOIs	https://doi.org/10.1002/anie.201602997 https://doi.org/10.1002/ange.201602997
State	Published - May 30 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.

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title = "Super-heptazethrene",

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.",

author = "Wangdong Zeng and Zhe Sun and Herng, {Tun Seng} and Theo Goncalves and Gopalakrishna, {Tullimilli Y.} and Kuo-Wei Huang and Jun Ding and Jishan Wu",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.",

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month = may,

day = "30",

doi = "10.1002/anie.201602997",

language = "English (US)",

volume = "55",

pages = "8615--8619",

journal = "Angewandte Chemie International Edition",

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publisher = "John Wiley and Sons Ltd",

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T1 - Super-heptazethrene

AU - Zeng, Wangdong

AU - Sun, Zhe

AU - Herng, Tun Seng

AU - Goncalves, Theo

AU - Gopalakrishna, Tullimilli Y.

AU - Huang, Kuo-Wei

AU - Ding, Jun

AU - Wu, Jishan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.

PY - 2016/5/30

Y1 - 2016/5/30

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/623144

UR - http://doi.wiley.com/10.1002/anie.201602997

UR - http://www.scopus.com/inward/record.url?scp=84971577871&partnerID=8YFLogxK

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DO - 10.1002/anie.201602997

M3 - Article

C2 - 27240255

SN - 1433-7851

VL - 55

SP - 8615

EP - 8619

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 30

ER -

Super-heptazethrene

Abstract

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CCDC 1444589: Experimental Crystal Structure Determination : 5,9,14,18-tetrakis(3,5-bis(trifluoromethyl)phenyl)-7,16-di-t-butyl-4,13-dimethyl-5,14-dihydrobenzo[de]benzo[4,5]pentaceno[2,1,14,13,12,11-opqrstuva]pentacene

CCDC 1441884: Experimental Crystal Structure Determination : 7,14-bis(4-t-butyl-2,6-bis(methoxymethyl)phenyl)-5,12-dimethyldibenzo[c,pqr]tetraphene

CCDC 1441886: Experimental Crystal Structure Determination : (5,12-dimethyldibenzo[c,pqr]tetraphene-7,14-diyl)bis((5-t-butylbenzene-2,1,3-triyl)bis(methylene)) tetraacetate

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Super-heptazethrene

Abstract

Bibliographical note

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Datasets

CCDC 1444589: Experimental Crystal Structure Determination : 5,9,14,18-tetrakis(3,5-bis(trifluoromethyl)phenyl)-7,16-di-t-butyl-4,13-dimethyl-5,14-dihydrobenzo[de]benzo[4,5]pentaceno[2,1,14,13,12,11-opqrstuva]pentacene

CCDC 1441884: Experimental Crystal Structure Determination : 7,14-bis(4-t-butyl-2,6-bis(methoxymethyl)phenyl)-5,12-dimethyldibenzo[c,pqr]tetraphene

CCDC 1441886: Experimental Crystal Structure Determination : (5,12-dimethyldibenzo[c,pqr]tetraphene-7,14-diyl)bis((5-t-butylbenzene-2,1,3-triyl)bis(methylene)) tetraacetate

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