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9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units : A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior
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| Title: | 9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units : A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior |
| Authors: | Ishigaki, Yusuke Browse this author →KAKEN DB | | Hayashi, Yuki Browse this author | | Sugawara, Kazuma Browse this author | | Shimajiri, Takuya Browse this author | | Nojo, Wataru Browse this author | | Katoono, Ryo Browse this author | | Suzuki, Takanori Browse this author |
| Keywords: | polycyclic aromatic hydrocarbons | | long bond | | dynamic redox system | | dication | | dibenzotropylium | | electrochromism | | through-bond interaction |
| Issue Date: | Nov-2017 |
| Publisher: | MDPI |
| Journal Title: | Molecules |
| Volume: | 22 |
| Issue: | 11 |
| Start Page: | 1900 |
| Publisher DOI: | 10.3390/molecules22111900 |
| Abstract: | The title dispiro hydrocarbon 1 was designed as a new electrochromic material. This multiply clamped hexaphenylethane-type electron donor was prepared from 2,2'-diiodobiphenyl via biphenyl-2,2'-diylbis(dibenzotropylium) 2(2+) salt. X-ray analysis of 1 revealed a highly strained structure as reflected by an elongated ethane bond [bond length: 1.6665(17) angstrom] and nearly eclipsed conformation. The weakened bond was cleaved upon two-electron oxidation to regenerate the deeply colored dication 2(2+). The reversible interconversion between 1 and 2(2+) is accompanied not only by a drastic color change but also by C-C bond formation/cleavage. Thus, the voltammogram showed a pair of well-separated redox waves, which is characteristic of "dynamic redox (dyrex)" behavior. The tetrahydro derivative of 1 with two units of spiro(dibenzocycloheptadiene), which suffers from more severe steric congestion, was also prepared. The crystallographically determined bond length for the central C-C bond [1.705(4) angstrom] is greatest among the values reported for 9,9,10,10-tetraaryl-9,10-dihydrophenanthrene derivatives. |
| Rights: | © 2017 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). | | http://creativecommons.org/licenses/by/4.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/68293 |
| Appears in Collections: | 理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 石垣 侑祐
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