Structural properties of charge-transfer complexes of multilayered [3.3]paracyclophanes

Masahiko Shibahara; Motonori Watanabe; Chang Yuan; Kenta Goto; Teruo Shinmyozu

doi:10.1016/j.tetlet.2011.04.087

Structural properties of charge-transfer complexes of multilayered [3.3]paracyclophanes

Masahiko Shibahara, Motonori Watanabe, Chang Yuan, Kenta Goto, Teruo Shinmyozu

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

12 Citations (Scopus)

Abstract

In the solid state, multilayered [3.3]paracyclophanes (PCPs) 2-6 and tetracyanoethylene (TCNE) form charge-transfer (CT) complexes with a 1:1 stoichiometry. All the benzene rings overlapped each other. All the [3.3]PCP units and dione units assume chair conformations and the transannular distances are shorter than those of the corresponding free multilayered [3.3]PCP except for the dione unit in the four-layered dione 6. In the crystal-packing diagrams, the PCP and TCNE are located in alternating donor-acceptor stacking in columns, and effective short contacts are observed in the neighboring molecules.

Original language	English
Pages (from-to)	3371-3375
Number of pages	5
Journal	Tetrahedron Letters
Volume	52
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2011.04.087
Publication status	Published - Jun 29 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.04.087

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title = "Structural properties of charge-transfer complexes of multilayered [3.3]paracyclophanes",

abstract = "In the solid state, multilayered [3.3]paracyclophanes (PCPs) 2-6 and tetracyanoethylene (TCNE) form charge-transfer (CT) complexes with a 1:1 stoichiometry. All the benzene rings overlapped each other. All the [3.3]PCP units and dione units assume chair conformations and the transannular distances are shorter than those of the corresponding free multilayered [3.3]PCP except for the dione unit in the four-layered dione 6. In the crystal-packing diagrams, the PCP and TCNE are located in alternating donor-acceptor stacking in columns, and effective short contacts are observed in the neighboring molecules.",

author = "Masahiko Shibahara and Motonori Watanabe and Chang Yuan and Kenta Goto and Teruo Shinmyozu",

note = "Funding Information: T.S. wishes to thank the Theme Project (Professor Tahsin J. Chow), Institute of Chemistry, Academia Sinica, Taiwan ROC, for the financial support of this study. We are also grateful for the financial support by a Grant-in-Aid for Scientific Research on Innovative Areas ( No. 21106015 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. This work was performed under the Cooperative Research Program of {\textquoteleft}Network Joint Research Center for Materials and Devices (IMCE, Kyushu University){\textquoteright}. ",

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T1 - Structural properties of charge-transfer complexes of multilayered [3.3]paracyclophanes

AU - Shibahara, Masahiko

AU - Watanabe, Motonori

AU - Yuan, Chang

AU - Goto, Kenta

AU - Shinmyozu, Teruo

N1 - Funding Information: T.S. wishes to thank the Theme Project (Professor Tahsin J. Chow), Institute of Chemistry, Academia Sinica, Taiwan ROC, for the financial support of this study. We are also grateful for the financial support by a Grant-in-Aid for Scientific Research on Innovative Areas ( No. 21106015 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. This work was performed under the Cooperative Research Program of ‘Network Joint Research Center for Materials and Devices (IMCE, Kyushu University)’.

PY - 2011/6/29

Y1 - 2011/6/29

N2 - In the solid state, multilayered [3.3]paracyclophanes (PCPs) 2-6 and tetracyanoethylene (TCNE) form charge-transfer (CT) complexes with a 1:1 stoichiometry. All the benzene rings overlapped each other. All the [3.3]PCP units and dione units assume chair conformations and the transannular distances are shorter than those of the corresponding free multilayered [3.3]PCP except for the dione unit in the four-layered dione 6. In the crystal-packing diagrams, the PCP and TCNE are located in alternating donor-acceptor stacking in columns, and effective short contacts are observed in the neighboring molecules.

AB - In the solid state, multilayered [3.3]paracyclophanes (PCPs) 2-6 and tetracyanoethylene (TCNE) form charge-transfer (CT) complexes with a 1:1 stoichiometry. All the benzene rings overlapped each other. All the [3.3]PCP units and dione units assume chair conformations and the transannular distances are shorter than those of the corresponding free multilayered [3.3]PCP except for the dione unit in the four-layered dione 6. In the crystal-packing diagrams, the PCP and TCNE are located in alternating donor-acceptor stacking in columns, and effective short contacts are observed in the neighboring molecules.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Structural properties of charge-transfer complexes of multilayered [3.3]paracyclophanes

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