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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
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 (
Type: article
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)

Submitter: 石垣 侑祐

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