Redox Switching of Conjugation Length Using 9,9,10,10-Tetraaryl-9,10-dihydrophenanthrene as an ON/OFF Unit: Preparation, X-ray Structure, and Redox Properties of Perfluorobiphenyl Derivative and Its S<sub>N</sub>Ar Reactions to π-Extended Analogues
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- Suzuki Takanori
- Department of Chemistry, Faculty of Science, Hokkaido University
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- Tamaoki Hitomi
- Department of Chemistry, Faculty of Science, Hokkaido University
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- Katoono Ryo
- Department of Chemistry, Faculty of Science, Hokkaido University
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- Fujiwara Kenshu
- Department of Chemistry, Faculty of Science, Hokkaido University
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- Ichikawa Junji
- Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
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- Fukushima Takanori
- Chemical Resources Laboratory, Tokyo Institute of Technology
Bibliographic Information
- Other Title
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- Redox Switching of Conjugation Length Using 9,9,10,10-Tetraaryl-9,10-dihydrophenanthrene as an ON/OFF Unit: Preparation, X-ray Structure, and Redox Properties of Perfluorobiphenyl Derivative and Its SNAr Reactions to π-Extended Analogues
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Abstract
Octafluorobiphenyl-2,2′-diylbis(diarylmethylium) dye 2a2+ prepared from 1,2-dibromotetrafluorobenzene is interconvertible with colorless dihydrophenanthrene donor 1a. By the SNAr reactions of 1a with acetylides, π-extended analogues 1b and 1c were obtained. Their electrochromic behavior is accompanied by a drastic absorption change not only in the visible but also UV region, because the torsion angle of the biaryl unit is modified upon redox reactions.
Journal
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- Chemistry Letters
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Chemistry Letters 42 (7), 703-705, 2013
The Chemical Society of Japan
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Details
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- CRID
- 1390282679565029248
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- NII Article ID
- 10031183265
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- NII Book ID
- AA00603318
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- COI
- 1:CAS:528:DC%2BC3sXhtF2ntbnJ
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- ISSN
- 13480715
- 03667022
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- Text Lang
- en
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- Data Source
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- JaLC
- Crossref
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed