Creation of organic redox systems exhibiting electrochemical switching for the development of unimolecular devices
| Project/Area Number |
14540486
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Hirosaki University (2003-2004)
Tohoku University (2002) |
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Principal Investigator |
ITO Shunji Hirosaki University, Faculty of Science and Technology, Professor, 理工学部, 教授 (10213042)
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| Project Period (FY) |
2002 – 2004
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| Project Status |
Completed (Fiscal Year 2004)
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| Budget Amount *help |
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2003: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2002: ¥1,600,000 (Direct Cost: ¥1,600,000)
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| Keywords | Unimolecular device / Organic redox system / Cyanine dye / Electrochromism / Cross-coupling reaction / Organometallics / π-Conjugated compound / Nonbenzenoidaromatics / 分子スイッチ / ディスコティック液晶 |
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| Research Abstract |
Creation of molecular devices has been examined utilizing the redox systems with one-electron transfer for the transmission of information. The low stability of the radical ionic state hampered the design of novel molecular devices. We applied the closed shell system produced by two-electron transfer for the improvement of the stability. We have prepared several responsive molecules by the concept of one-step two-electron transfer utilizing the azulene derivatives substituted by 2-or 6-positions, which were archived by the transition metal catalyzed reaction. The solubility of the compounds was improved by the introduction of octyl groups or hexyloxycarbonyl groups on the azulene rings. We have also prepared azulene derivatives with ethynyl spacers. The redox behavior of the novel π-conjugated compounds was examined by cyclic voltammetry. These compounds exhibited the presumed multiple electron transfer depending on the number of azulene rings. We anticipate that these new azulene derivatives should exhibit multiple color change depending on the redox state owing to the concept of cyanine-cyanine hybrid proposed by us recently. These compounds also exhibit liquid crystalline behavior in addition to the redox behavior. We also prepared p-phenylenediamines substituted by 6-azulenyl groups, which exhibited amphoteric redox behavior. Furthermore, we have developed novel organometallic reagents of azulenes and also revealed bond-length alternation on the 1-azulenylmethyl cations.
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Report
(4 results)
Research Products
(35 results)
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[Journal Article] Azulene-Substituted Aromatic Amines Synthesis and Amphoteric Redox Behavior of N,N-Di(6-azulenyl)-p-toluidine and N,N,N,N-Tetra(6-azulenyl)-p-phenylenediamine and their Derivatives2005
Author(s)
S.Ito, T.Kubo, N.Morita, T.Ikoma, S.Tero-Kubota, J.Kawakami, A.Tajiri
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Journal Title
The Journal of Organic Chemistry 70(6)
Pages: 2285-2293
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Synthesis, Stability and Bonding Situation of Tris-, Bis-and Mono[9-(azuleno[1,2-b]thienyl)]-methyl Cations2003
Author(s)
S.Ito, T.Kubo, M.Kondo, C.Kabuto, N.Morita, T.Asao, K.Fujimori, M.Watanabe, N.Harada, M.Yasunami
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Journal Title
Organic & Bnmolecular Chemistry 1(14)
Pages: 2572-2580
Description
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