Highly Twisted 1,2:8,9-Dibenzozethrenes: Synthesis, Ground State, and Physical Properties
Two soluble and stable 1,2:8,9‐dibenzozethrene derivatives (3 a,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...
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| Published in | ChemPlusChem (Weinheim, Germany) Vol. 79; no. 11; pp. 1549 - 1553 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.11.2014
WILEY‐VCH Verlag Wiley |
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| Online Access | Get full text |
| ISSN | 2192-6506 2192-6506 |
| DOI | 10.1002/cplu.201402127 |
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| Abstract | Two soluble and stable 1,2:8,9‐dibenzozethrene derivatives (3 a,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 far‐red/near‐infrared absorption/emission and amphoteric redox behaviors.
Twisted zethrene! Highly twisted 1,2:8,9‐dibenzozethrenes are synthesized and isolated in crystalline form (see figure). They are found to have a small biradical character with a small energy gap, showing NIR emission and amphoteric redox behavior. |
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| AbstractList | Two soluble and stable 1,2:8,9-dibenzozethrene derivatives (3,a,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 singlettriplet energy gap; these predictions are supported by NMR and electronic absorption measurements. They have small energy gaps and exhibit far-red/near-infrared absorption/emission and amphoteric redox behaviors. Two soluble and stable 1,2:8,9‐dibenzozethrene derivatives ( 3 a,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 far‐red/near‐infrared absorption/emission and amphoteric redox behaviors. Two soluble and stable 1,2:8,9‐dibenzozethrene derivatives (3 a,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 far‐red/near‐infrared absorption/emission and amphoteric redox behaviors. Twisted zethrene! Highly twisted 1,2:8,9‐dibenzozethrenes are synthesized and isolated in crystalline form (see figure). They are found to have a small biradical character with a small energy gap, showing NIR emission and amphoteric redox behavior. |
| Author | Wu, Jishan Zheng, Bin Huang, Kuo-Wei Sun, Zhe Hu, Pan |
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| Keywords | density functional calculations ZETHRENE POLYCYCLIC AROMATIC-HYDROCARBONS cyclodimerization amphoteric redox behavior PHOTOPHYSICAL PROPERTIES INDEX OPEN-SHELL biradical polycycles |
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| References_xml | – reference: Z. Sun, J. Wu, J. Org. Chem. 2013, 78, 9032-9040. – reference: T. Weil, T. Vosch, J. Hofkens, K. Peneva, K. Müllen, Angew. Chem. 2010, 122, 9252-9278; – reference: Y. Ruiz-Morales, J. Phys. Chem. A 2002, 106, 11283-11308. – reference: L. Shan, Z. Liang, X. Xu, Q. Tang, Q. Miao, Chem. Sci. 2013, 4, 3294-3297. – reference: Angew. Chem. Int. Ed. 2010, 49, 7059-7062. – reference: Angew. Chem. Int. Ed. 2008, 47, 452-483; – reference: Y. Li, W.-K. Heng, B. S. Lee, N. Aratani, J. L. Zafra, N. Bao, R. Lee, Y. M. Sung, Z. Sun, K.-W. Huang, R. D. Webster, J. T. López Navarrete, D.-H. Kim, A. Osuka, J. Casado, J. Ding, J. Wu, J. Am. Chem. Soc. 2012, 134, 14913-14922. – reference: Z. Sun, J. Wu, J. Mater. Chem. 2012, 22, 4151-4160; – reference: D. Désilets, P. M. Kazmaier, R. A. Burt, Can. J. Chem. 1995, 73, 319-324; – reference: E. Clar, I. A. Macpherson, H. Schulz-Kiesow, Liebigs Ann. 1963, 669, 44-52. – reference: M. Nakano, R. Kishi, A. Takebe, M. Nate, H. 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| Snippet | Two soluble and stable 1,2:8,9‐dibenzozethrene derivatives (3 a,b) are synthesized through a palladium‐catalyzed cyclodimerization reaction. X‐ray... Two soluble and stable 1,2:8,9‐dibenzozethrene derivatives ( 3 a,b ) are synthesized through a palladium‐catalyzed cyclodimerization reaction. X‐ray... Two soluble and stable 1,2:8,9-dibenzozethrene derivatives (3,a,b) are synthesized through a palladium-catalyzed cyclodimerization reaction. X-ray... |
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| SubjectTerms | amphoteric redox behavior biradical Chemistry Chemistry, Multidisciplinary cyclodimerization density functional calculations Physical Sciences polycycles Science & Technology |
| Title | Highly Twisted 1,2:8,9-Dibenzozethrenes: Synthesis, Ground State, and Physical Properties |
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