Construction of organic electrochromic materials composed by multiple redox system

• Project/Area Number: 22850007
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Shinshu University
• Principal Investigator: SHOJI Taku 信州大学, 理学部, 助教 (60581014)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥3,107,000 (Direct Cost: ¥2,390,000、Indirect Cost: ¥717,000); Fiscal Year 2011: ¥1,495,000 (Direct Cost: ¥1,150,000、Indirect Cost: ¥345,000); Fiscal Year 2010: ¥1,612,000 (Direct Cost: ¥1,240,000、Indirect Cost: ¥372,000)
• Keywords: π電子系化合物 / アズレン / フェロセン / カルボカチオン / ドナー・アクセプターシステム / エレクトロクロミズム / 環化付加反応 / クロスカップリング反応 / サイクリックボルタンメトリー / サクリックボルタンメトリー

Research Abstract

The redox active novelπ-electron systems substituted by azulene, 2H-cycloheptabfuran-2-one and ferrocene were prepared. The electronic property novelπ-electron systems of was examined by UV/Vis spectroscopy and theoretical calculations. Electrochromic property of novelπ-electron systems was investigated by UV/Vis spectroscopy under electrochemical reaction.

Research Products

• [Journal Article] Synthesis and Redox Behavior of Cyanovinyl-substituted 2H-Cyclohepta[ b] furan-2-ones (2012)
  • Author(s): Taku Shoji, Junya Higashi, Shunji Ito, Mitsunori Oda, Masafumi Yasunami
  • Journal Title: Heterocycles
  • Peer Reviewed
• [Journal Article] Facile Synthesis of 2, 3-DisubstitutedPyrroles from 2-Substituted 1-Pyrrolines (2012)
  • Author(s): Yurie Fujiwara, Mitsunori Oda, Taku Shoji, Takako Abe, Shigeyasu Kuroda
  • Journal Title: Heterocycles Volume: 85 Pages: 1187-1195
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Mono-, Bis-, Tris-and Tetrakis[ 1, 1, 4, 4-tetracyano-2-(1-azulenyl)-1, 3-butadien-3-yl] Chromophores Connected to a Benzene Ring by Phenylethynyl-and 2-Thienylethynyl Spacers (2012)
  • Author(s): Taku Shoji, Mitsuhisa Maruyama, Shunji Ito, Noboru Morita
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: (in press) Issue: 7 Pages: 761-773
  • DOI: 10.1246/bcsj.20120037
  • NAID: 130004153086
  • Peer Reviewed
• [Journal Article] First synthesis of 1-(indol-2-yl) azulenes by the Vilsmeier-Haack type arylation with triflic anhydride as an activating reagent (2012)
  • Author(s): Taku Shoji, Yuta Inoue, Shunji Ito
  • Journal Title: Tetrahedron Lett. Volume: 53 Pages: 1493-1496
  • Peer Reviewed
• [Journal Article] Synthesis of donor acceptor chromophores by the[ 2+ 2] cycloaddition of arylethynyl-2H-cyclohepta[ b] furan-2-ones with 7, 7, 8, 8-tetracyanoquinodimethane (2012)
  • Author(s): Taku Shoji, Junya Higashi, Shunji Ito, Tetsuo Okujima, Masafumi Yasunami, Noboru Morita
  • Journal Title: Organic & Biomolecular Chemistry Volume: 10 Pages: 2431-2438
  • NAID: 120007114268
  • Peer Reviewed
• [Journal Article] First Synthesis of 2-Heteroarylazulenes by the Electrophilic Substitution of Azulene with Triflate of N-Containing Heterocycles (2012)
  • Author(s): Taku Shoji, Yuta Inoue, Shunji Ito, Tetsuo Okujima, Noboru Morita
  • Journal Title: Heterocycles Volume: 85 Pages: 35-41
  • NAID: 120007114260
  • Peer Reviewed
• [Journal Article] Facile Synthesis of 2,3-Disubstituted Pyrroles from 2-Substituted 1-Pyrrolines (2012)
  • Author(s): Mitsunori Oda, Taku Shoji, et al
  • Journal Title: Heterocycles Volume: (in press) Issue: 5 Pages: 1187-1187
  • DOI: 10.3987/com-12-12457
  • NAID: 120007114283
  • Peer Reviewed
• [Journal Article] First synthesis of 1-(indol-2-yl) azulenes by the Vilsmeier-Haack type arylation with triflic anhydride as an activating reagent (2012)
  • Author(s): Taku Shoji, et al
  • Journal Title: Tetrahedron Letters Volume: 53 Issue: 12 Pages: 1493-1496
  • DOI: 10.1016/j.tetlet.2012.01.044
  • Peer Reviewed
• [Journal Article] Synthesis of donor-acceptor chromophores by the [2+2] cycloaddition of arylethy nyl-2H-cyclohepta[b]furan-2-ones with 7,7,8,8-tetracyanoquinodimethane (2012)
  • Author(s): Taku Shoji, et al
  • Journal Title: Organic & Biomolecular Chemistry Volume: 10 Issue: 12 Pages: 2431-2438
  • DOI: 10.1039/c2ob06931h
  • Peer Reviewed
• [Journal Article] Recent Advances in the Development of Methods for the Preparation of Functionalized Azulenes for Electrochromic Applications (2011)
  • Author(s): Shunji Ito, Taku Shoji, Noboru Morita
  • Journal Title: Synlett Volume: 16 Pages: 2279-2298
  • Peer Reviewed
• [Journal Article] The[ 2+ 2] Cycloaddition Reaction of Ethynylated 2H-Cyclohepta[ b] furan-2-ones with 2, 3-Dichloro-5, 6-dicyano-1, 4-benzoquino ne (2011)
  • Author(s): Taku Shoji, Junya Higashi, Shunji Ito, Masafumi Yasunami, Noboru Morita
  • Journal Title: Heterocycles Volume: 83 Pages: 2271-2274
  • Peer Reviewed
• [Journal Article] Synthesis of 1-Heteroaryl-and 1, 3-Bis(heteroaryl) azulenes : Electrophilic Heteroarylation of Azulenes with the Triflate of N-Containing Heteroarenes (2011)
  • Author(s): Taku Shoji, Shunji Ito, Jyunya Higashi, Noboru Morita
  • Journal Title: Eur. J. Org. Chem. Pages: 5311-5322
  • Peer Reviewed
• [Journal Article] Synthesis and[ 2+ 2] Cycloaddition with Tetracyanoethylene of Ene-Diyne Scaffolds Bearing Ferrocenes at the Periphery (2011)
  • Author(s): Taku Shoji, Shunji Ito, Tetsuo Okujima, Noboru Morita
  • Journal Title: Eur. J. Org. Chem. Pages: 5134-5140
  • Peer Reviewed
• [Journal Article] Synthesis of Redox-Active, Intramolecular Charge-Transfer Chromophores by the[ 2+ 2] Cycloaddition of Ethynylated 2H-Cyclohepta[ b] furan-2-ones with Tetracyanoethylene (2011)
  • Author(s): T. Shoji, J. Higashi, S. Ito, T. Okujima, M. Yasunami, N. Morita
  • Journal Title: Chem. Eur. J. Volume: 17 Pages: 5116-5129
  • Peer Reviewed
• [Journal Article] Synthesis and Redox Behavior of Bis(3-methylthio-1-azulenyl) methyl Cations and Dications Connected by 2-Thienyl and 2, 5-Thiophenediyl Spacers (2011)
  • Author(s): T. Shoji, J. Higashi, S. Ito, T. Okujima, N. Morita
  • Journal Title: Eur. J. Org. Chem. Pages: 584-592
  • Peer Reviewed
• [Journal Article] Recent Advances in the Development of Methods for the Preparation of Functionalized Azulenes for Electrochromic Applications (2011)
  • Author(s): S.Ito, T.Shoji, N.Morita
  • Journal Title: Synlett Volume: 16 Issue: 16 Pages: 2279-2298
  • DOI: 10.1055/s-0030-1260316
  • Peer Reviewed
• [Journal Article] The [2+2] Cycloaddition Reaction of Ethynylated 2H-Cyclohepta[b]furan-2-ones with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (2011)
  • Author(s): Taku Shoji, et al
  • Journal Title: Heterocycles Volume: 83 Issue: 10 Pages: 2271-2274
  • DOI: 10.3987/com-11-12303
  • NAID: 120007114261
  • Peer Reviewed
• [Journal Article] Synthesis of 1-Heteroaryl- and 1,3-Bis(heteroaryl) azulenes : Electrophilic Heteroaryl ation of Azulenes with the Triflate of N-Containing Heteroarenes (2011)
  • Author(s): Taku Shoji, et al
  • Journal Title: European Journal of Organic Chemistry Volume: 2011 Issue: 27 Pages: 5311-5322
  • DOI: 10.1002/ejoc.201100498
  • Peer Reviewed
• [Journal Article] Synthesis and [2+2] Cycloaddition with Tetracyanoethylene of Ene-Diyne Scaffolds Bearing Ferrocenes at the Periphery (2011)
  • Author(s): Taku Shoji, et al
  • Journal Title: European Journal of Organic Chemistry Volume: 2011 Issue: 26 Pages: 5134-5140
  • DOI: 10.1002/ejoc.201100650
  • Peer Reviewed
• [Journal Article] Synthesis, Properties, and Redox Behavior of Ferrocene-substituted Bis(3-methylthio-1-azulenyl) methylium Ions (2010)
  • Author(s): T. Shoji, J. Higashi, S. Ito, N. Morita
  • Journal Title: Eur. J. Inorg. Chem. Pages: 4886-4891
  • Peer Reviewed
• [Journal Article] Synthesis of 1-(pyridyl, quinolyl, and isoquinolyl) azulenes by Reissert-Henze type reaction (2010)
  • Author(s): T. Shoji, K. Okada, S. Ito, K. Toyota, N. Morita
  • Journal Title: Tetrahedron Lett. Volume: 51 Pages: 5127-5130
  • NAID: 120007114266
  • Peer Reviewed
• [Journal Article] Synthesis of 5-Heteroaryl-and 5, 7-Bis(heteroaryl) azulenes by Electrophilic Substitution of 1, 3-Di-tert-Butylazulene with Triflates of N-Containing Heterocycles (2010)
  • Author(s): T. Shoji, S. Ito, K. Toyota, N. Morita
  • Journal Title: Eur. J. Org. Chem. Pages: 1059-1069
  • Peer Reviewed
• [Journal Article] Synthesis of Redox-Active, Intramolecular Charge-Transfer Chromophores by the [2+2] Cycloaddition of Ethynylated 2H-Cyclohepta[b]furan-2-ones with Tetracyanoe thylene (2010)
  • Author(s): Taku Shoji
  • Journal Title: Chemistry-A European Journal Volume: 17 Pages: 5116-5129
  • Peer Reviewed
• [Journal Article] Synthesis and Redox Behavior of Bis(3-methylthio-1-azulenyl)methyl Cations and Dications Connected by 2-Thienyl and 2,5-Thiophenediyl Spacers (2010)
  • Author(s): Taku Shoji
  • Journal Title: European Journal of Organic Chemistry Pages: 584-592
  • Peer Reviewed
• [Journal Article] Synthesis, Properties, and Redox Behavior of Ferrocene-substituted Bis(3-methylthio-1-azulenyl)methylium Ions (2010)
  • Author(s): Taku Shoji
  • Journal Title: European Journal of Inorganic Chemistry Pages: 4886-4891
  • Peer Reviewed
• [Presentation] π電子系コアに連結したアズレニルテトラシアノブタジエンの合成と性質 (2012)
  • Author(s): 庄子卓,丸山満久,伊東俊司,森田昇
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学,横浜
  • Year and Date: 2012-03-25
• [Presentation] π電子系コアに連結したアズレニルテトラシアノブタジエンの合成と性質 (2012)
  • Author(s): 庄子卓
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 2012-03-25
• [Presentation] 1, 3-ジアズレニルエチニルアズレンの合成と反応性 (2011)
  • Author(s): 庄子卓,丸山満久,伊東俊司,奥島鉄雄
  • Organizer: 平成23年度化学系学協会東北大会
  • Place of Presentation: 東北大学,仙台
  • Year and Date: 2011-09-17
• [Presentation] 求電子置換反応を経由した2-ヘテロアリールアズレン類の合成 (2011)
  • Author(s): 庄子卓,井上雄太,伊東俊司,奥島鉄雄
  • Organizer: 平成23年度化学系学協会東北大会
  • Place of Presentation: 東北大学,仙台
  • Year and Date: 2011-09-17
• [Presentation] 1,3-ジアズレニルエチニルアズレンの合成と反応性 (2011)
  • Author(s): 庄子卓
  • Organizer: 平成23年度化学系学協会東北大会
  • Place of Presentation: 東北大学
  • Year and Date: 2011-09-17
• [Presentation] 求電子置換反応を経由した2-ヘテロアリールアズレン類の合成 (2011)
  • Author(s): 庄子卓
  • Organizer: 平成23年度化学系学協会東北大会
  • Place of Presentation: 東北大学
  • Year and Date: 2011-09-17
• [Presentation] π 電子系コアに連結した2H-シクロヘプタ[b]フラン-2-オンクロモフォアの合成と酸化還元的挙 (2010)
  • Author(s): 庄子卓,東隼也,伊東俊司,奥島鉄雄,安並正文,豊田耕三,森田昇
  • Organizer: 第40 回複素環化学討論会
  • Place of Presentation: 仙台市民会館,仙台
  • Year and Date: 2010-10-14
• [Presentation] 非対称なジアズレニルアセチレン誘導体の合成と酸化還元的挙動 (2010)
  • Author(s): 庄子卓,伊東俊司,豊田耕三,森田昇
  • Organizer: 平成22年度化学系学協会東北大会
  • Place of Presentation: 岩手大学,盛岡
  • Year and Date: 2010-09-25
• [Presentation] アリールアミンに連結したアズレニルテトラシアノブタジエンクロモフォアの合成 (2010)
  • Author(s): 庄子卓
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋大学
  • Year and Date: 2010-09-10
• [Presentation] アリールアミンに連結したアズレニルテトラシアノブタジエンクロモフォアの合成 (2010)
  • Author(s): 庄子卓,伊東俊司,奥島鉄雄,安並正文,森田昇
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋大学,名古屋
  • Year and Date: 2010-09-09
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