Highly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties

Zhe Sun; Bin Zheng; Pan Hu; Kuo-Wei Huang; Jishan Wu

doi:10.1002/cplu.201402127

Highly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties

Zhe Sun, Bin Zheng, Pan Hu, Kuo-Wei Huang, Jishan Wu

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

Two soluble and stable 1,2:8,9-dibenzozethrene derivatives (3a,b) are synthesized through a palladium-catalyzed cyclodimerization reaction. X-ray crystallographic analysis shows that these molecules are highly twisted owing to congestion at the cove region. Broken-symmetry DFT calculations predict that they have a singlet biradical ground state with a smaller biradical character and a large singlet-triplet energy gap; these predictions are supported by NMR and electronic absorption measurements. They have small energy gaps and exhibit farred/near-infrared absorption/emission and amphoteric redox behaviors.

Original language	English (US)
Pages (from-to)	1549-1553
Number of pages	5
Journal	ChemPlusChem
Volume	79
Issue number	11
DOIs	https://doi.org/10.1002/cplu.201402127
State	Published - Aug 8 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: J.W. acknowledges financial support from the BMRC grant (10/1/21/19/642), MOE Tier 2 grant (MOE2011-T2-2-130), and MINDEF-NUS JPP (Grant 12-02-05). K.W.H. acknowledges support from MUST. We thank Dr. Tan Geok Kheng for the crystallographic analysis of 3b.

ASJC Scopus subject areas

General Chemistry

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10.1002/cplu.201402127

Cite this

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title = "Highly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties",

abstract = "Two soluble and stable 1,2:8,9-dibenzozethrene derivatives (3a,b) are synthesized through a palladium-catalyzed cyclodimerization reaction. X-ray crystallographic analysis shows that these molecules are highly twisted owing to congestion at the cove region. Broken-symmetry DFT calculations predict that they have a singlet biradical ground state with a smaller biradical character and a large singlet-triplet energy gap; these predictions are supported by NMR and electronic absorption measurements. They have small energy gaps and exhibit farred/near-infrared absorption/emission and amphoteric redox behaviors.",

author = "Zhe Sun and Bin Zheng and Pan Hu and Kuo-Wei Huang and Jishan Wu",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: J.W. acknowledges financial support from the BMRC grant (10/1/21/19/642), MOE Tier 2 grant (MOE2011-T2-2-130), and MINDEF-NUS JPP (Grant 12-02-05). K.W.H. acknowledges support from MUST. We thank Dr. Tan Geok Kheng for the crystallographic analysis of 3b.",

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AU - Sun, Zhe

AU - Zheng, Bin

AU - Hu, Pan

AU - Huang, Kuo-Wei

AU - Wu, Jishan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: J.W. acknowledges financial support from the BMRC grant (10/1/21/19/642), MOE Tier 2 grant (MOE2011-T2-2-130), and MINDEF-NUS JPP (Grant 12-02-05). K.W.H. acknowledges support from MUST. We thank Dr. Tan Geok Kheng for the crystallographic analysis of 3b.

PY - 2014/8/8

Y1 - 2014/8/8

N2 - Two soluble and stable 1,2:8,9-dibenzozethrene derivatives (3a,b) are synthesized through a palladium-catalyzed cyclodimerization reaction. X-ray crystallographic analysis shows that these molecules are highly twisted owing to congestion at the cove region. Broken-symmetry DFT calculations predict that they have a singlet biradical ground state with a smaller biradical character and a large singlet-triplet energy gap; these predictions are supported by NMR and electronic absorption measurements. They have small energy gaps and exhibit farred/near-infrared absorption/emission and amphoteric redox behaviors.

AB - Two soluble and stable 1,2:8,9-dibenzozethrene derivatives (3a,b) are synthesized through a palladium-catalyzed cyclodimerization reaction. X-ray crystallographic analysis shows that these molecules are highly twisted owing to congestion at the cove region. Broken-symmetry DFT calculations predict that they have a singlet biradical ground state with a smaller biradical character and a large singlet-triplet energy gap; these predictions are supported by NMR and electronic absorption measurements. They have small energy gaps and exhibit farred/near-infrared absorption/emission and amphoteric redox behaviors.

UR - http://hdl.handle.net/10754/563695

UR - http://doi.wiley.com/10.1002/cplu.201402127

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DO - 10.1002/cplu.201402127

M3 - Article

SN - 2192-6506

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EP - 1553

JO - ChemPlusChem

JF - ChemPlusChem

IS - 11

ER -

Highly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties

Abstract

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CCDC 980734: Experimental Crystal Structure Determination : 9,18-bis(4-t-butylphenyl)-5,14-bis((4-t-butylphenyl)ethynyl)dinaphtho[3,2,1-de:3',2',1'-mn]tetracene chloroform solvate

Cite this

Highly twisted 1,2:8,9-dibenzozethrenes: Synthesis, ground state, and physical properties

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

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CCDC 980734: Experimental Crystal Structure Determination : 9,18-bis(4-t-butylphenyl)-5,14-bis((4-t-butylphenyl)ethynyl)dinaphtho[3,2,1-de:3',2',1'-mn]tetracene chloroform solvate

Cite this