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テトラアリール-o-キノジメタン：二電子還元による発生・単離と高度に歪んだ分子構造
| Title: | テトラアリール-o-キノジメタン：二電子還元による発生・単離と高度に歪んだ分子構造 |
| Other Titles: | Tetraaryl-o-quinodimethanes: Reductive Generation and Severely Distorted Geometry |
| Authors: | 岩下, 新一1 Browse this author | | 鈴木, 孝紀2 Browse this author |
| Authors(alt): | Iwashita, Shinichi1 | | Suzuki, Takanori2 |
| Keywords: | o-quinodimethane | | steric repulsion | | strained molecule | | X-ray structure | | electrocyclization | | hydrogen shift | | electrochromism | | redox system | | dication | | dye |
| Issue Date: | Sep-2006 |
| Publisher: | 有機合成化学協会 |
| Citation: | 有機合成化学協会誌 (Journal of Synthetic Organic Chemistry Japan) |
| Volume: | 64 |
| Issue: | 9 |
| Start Page: | 958 |
| End Page: | 968 |
| Abstract: | Introduction of four aryl groups on the highly reactive o-quinodimethane (o-QDM) skeleton suppresses the intermolecular reactivities. Thus, the unimolecular isomerization through electrocyclization is the major decomposition path for title molecules. Rational design can prevent thermal isomerization of Ar4-o-QDMs. A new general procedure to generate Ar4-o-QDM has been established here that includes two-electron reduction of the corresponding dications, whose reaction conditions no longer promote electrocyclization of Ar4-o-QDM. Several derivatives of Ar4-o-QDM with the dihydrophenanthrene, dibenzoperylene, or acenaphthene skeleton were isolated for the first time, and the details on their highly strained molecular structures were investigated by low-temperature X-ray analyses. Based on the reversible interconversion between Ar4-o-QDMs and the precursor dications, they represent a new class of electrochromic redox pairs. |
| Rights: | ©有機合成化学協会 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/14770 |
| 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: 鈴木 孝紀
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