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Construction of assembled aromatic ring systems aimed for the organic electrochromic materials

Research Project

Project/Area Number 25810019
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionShinshu University

Principal Investigator

SHOJI Taku  信州大学, 学術研究院理学系, 助教 (60581014)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2015: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2014: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsアズレン / フェロセン / アリールアミン / 環化付加反応 / ドナー・アクセプターシステム / サイクリックボルタンメトリー / エレクトロクロミズム / アリールアズレン / 1,2'-ビアズレン / クロスカップリング反応
Outline of Final Research Achievements

Novel aromatic compounds based on donor-acceptor systems were prepared by the [2+2]cycloaddition-retroelectrocyclization sequence of alkyne derivatives with tetracyanoethylene and 7,7,8,8-tetracyanoquinodimethane in good to excellent yield. Intramolecular CT absorption bands were found in UV/Vis spectra of the TCBD and DCNQ chromophores. Analyses by CV and DPV showed that the TCBD and DCNQ chromophores exhibited a reversible multi-stage reduction wave. TCBD and DCNQ derivatives exhibited significant color changes with high reversibility, attributable to the stabilization of anionic species during the electrochemical reaction.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (33 results)

All 2016 2015 2014 2013 Other

All Journal Article (18 results) (of which Peer Reviewed: 18 results,  Acknowledgement Compliant: 12 results) Presentation (9 results) Remarks (6 results)

  • [Journal Article] Synthesis of 1,2’-Biazulenes by Palladium-Catalyzed Unusual Homo-coupling Reaction of 1-Haloazulenes in the Presence of Ferrocene2016

    • Author(s)
      Taku Shoji,* Kanami Miyashita, Takanori Araki, Miwa Tanaka, Akifumi Maruyama, Ryuta Sekiguchi, Shunji Ito, Tetsuo Okujima
    • Journal Title

      SYNTHESIS

      Volume: 48 Issue: 15 Pages: 2438-2448

    • DOI

      10.1055/s-0035-1561418

    • NAID

      120007100282

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Properties of (3-Phenyl-1-azulenyl)tetracyanobetadienes and Tris(aryltetracyanobetadiene)s Connected with 1,3,5-Tri(1-azulenyl)benzene Core2016

    • Author(s)
      Taku Shoji,* Akifumi Maruyama, Miwa Tanaka, Daichi Nagai, Erika Shimomura, Kunihide Fujimori, Shunji Ito, Tetsuo Okujima, Kozo Toyota, Masafumi Yasunami
    • Journal Title

      ChemistrySelect

      Volume: 1 Issue: 1 Pages: 49-56

    • DOI

      10.1002/slct.201500036

    • NAID

      120007100281

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2- and 6-thienylazulenes by palladium-catalyzed direct arylation of 2- and 6-haloazulenes with thiophene derivatives2015

    • Author(s)
      Taku Shoji,* Akifumi Maruyama, Takanori Araki, Shunji Ito and Tetsuo Okujima
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 13 Issue: 40 Pages: 10191-10197

    • DOI

      10.1039/c5ob01317h

    • NAID

      120007100278

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Properties and Redox Behavior of Ferrocenyl-1,1,4,4-tetracyano-1,3-butadienes Connected by Arylamine and Azobenzene Spacers2015

    • Author(s)
      Taku Shoji,* Natsumi Kamata, Akifumi Maruyama, Shunji Ito, and Tetsuo Okujima
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 88 Issue: 9 Pages: 1338-1346

    • DOI

      10.1246/bcsj.20150165

    • NAID

      130005099087

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Properties and Redox Behavior of Tris[1-azulenyltetracyanobetadiene and 1-azulenylbis(tetracyanobetadiene)s] Connected with 1,3,5-Tri(1-azulenyl)benzene Core2015

    • Author(s)
      Taku Shoji,* Akifumi Maruyama, Erika Shimomura, Daichi Nagai, Shunji Ito, Tetsuo Okujima, and Kozo Toyota
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2015 Issue: 9 Pages: 1979-1990

    • DOI

      10.1002/ejoc.201403556

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2,6-Diaminoazulenes by the SNAr Reaction with Cyclic Amines2015

    • Author(s)
      Taku Shoji,* Yuki Fujiwara, Akifumi Maruyama, Mitsuhisa Maruyama, Shunji Ito, Masafumi Yasunami, Ryuji Yokoyama, Noboru Morita
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 1 Pages: 85-88

    • DOI

      10.3987/com-14-s(k)1

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Properties and Redox Behavior of 1,1,4,4-Tetracyano-2-ferrocenyl-1,3-butadienes Connected by Aryl, Biaryl and Teraryl Spacers2015

    • Author(s)
      Taku Shoji,* Akifumi Maruyama, Chisa Yaku, Natsumi Kamata, Shunji Ito, Tetsuo Okujima and Kozo Toyota
    • Journal Title

      Chemistry - A European Journal

      Volume: 21 Issue: 1 Pages: 402-409

    • DOI

      10.1002/chem.201405004

    • NAID

      120007100279

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2-Aryl- and 6-Heteroaryl-1,3-di(4-pyridyl)azulenes by Katritzky’s Pyridylation of 2-Aryl- and 6-Heteroarylazulenes2014

    • Author(s)
      Taku Shoji,* Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Masafumi Yasunami, Junya Higashi, and Noboru Morita
    • Journal Title

      Heterocycles

      Volume: 89 Issue: 11 Pages: 2588-2603

    • DOI

      10.3987/com-14-13102

    • NAID

      120007100269

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 1,3-Bis(tetracyano-2-azulenyl-3-butadienyl)azulenes by the [2 + 2] Cycloaddition-Retroelectrocyclization of 1,3-Bis(azulenylethynyl)azulenes with Tetracyanoethylene2014

    • Author(s)
      Taku Shoji,* Mitsuhisa Maruyama, Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota
    • Journal Title

      Chemistry - A European Journal

      Volume: 20 Issue: 37 Pages: 11903-11912

    • DOI

      10.1002/chem.201402939

    • NAID

      120007100277

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2,2’-Diamino-1,1’-biazulenes by the Copper-Catalyzed Homo-Coupling Reaction of 2-Aminoazulenes2014

    • Author(s)
      Taku Shoji,* Akifumi Maruyama, Atsuyo Yamamoto, Yuki Fujiwara, Shunji Ito, Tetsuo Okujima, Noboru Morita
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 7 Pages: 1122-1124

    • DOI

      10.1246/cl.140333

    • NAID

      130004868280

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Properties of 6-Methoxy- and 6-Dimethylamino-1-methylthio- and 1,3-Bis(methylthio)azulenes and Triflic Anhydride-Mediated Synthesis of Their Biaryl Derivatives2014

    • Author(s)
      Taku Shoji,* Akifumi Maruyama, Mitsuhisa Maruyama, Shunji Ito, Tetsuo Okujima, Junya Higashi, Kozo Toyota, Noboru Morita
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 87 Issue: 1 Pages: 141-154

    • DOI

      10.1246/bcsj.20130275

    • NAID

      130004153257

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Properties, and Crystal Structure of DDQ-Adducts of Ethynylated 2H-Cyclohepta[b]furan-2-ones2014

    • Author(s)
      Taku Shoji,* Mitsuhisa Maruyama, Erika Shimomura, Akifumi Maruyama, Shunji Ito, Masafumi Yasunami, Junya Higashi, Kozo Toyota, and Noboru Morita*
    • Journal Title

      Heterocycles

      Volume: 88 Issue: 1 Pages: 319-329

    • DOI

      10.3987/com-13-s(s)24

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Properties and Redox Behavior of Ene-Diyne Scaffolds Bearing 1- and 2-Azulenyl groups at the Periphery2013

    • Author(s)
      Taku Shoji,* Erika Shimomura, Mitsuhisa Maruyama, Shunji Ito, Tetsuo Okujima, Noboru Morita
    • Journal Title

      European Journal of Organic Chemistry

      Volume: なし Issue: 5 Pages: 957-964

    • DOI

      10.1002/ejoc.201201397

    • NAID

      120007100276

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 2-Azulenyl-1,1,4,4-tetracyano-3-ferrocenyl-1,3-butadienes by the [2+2] Cycloaddition of (Ferrocenylethynyl)azulenes with Tetracyanoethylene2013

    • Author(s)
      Taku Shoji,* Shunji Ito, Tetsuo Okujima, Noboru Morita
    • Journal Title

      Chemistry - A European Journal

      Volume: 19 Issue: 18 Pages: 5721-5730

    • DOI

      10.1002/chem.201202257

    • NAID

      120007100274

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Novel Thiophene-fused 1,1’-Biazulene Derivative by the Reaction of Azuleno[1,2-b]thiophene with N-Iodosuccinimide2013

    • Author(s)
      Taku Shoji,* Erika Shimomura, Yuta Inoue, Mitsuhisa Maruyama, Atsuyo Yamamoto, Kunihide Fujimori, Shunji Ito, Masafumi Yasunami, Noboru Morita
    • Journal Title

      Heterocycles

      Volume: 87 Issue: 2 Pages: 303-306

    • DOI

      10.3987/com-12-12638

    • NAID

      120007114366

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 1,6’-Bi- and 1,6’:3,6’’-Terazulenes from 1-Pyridyl- and 1,3-Di(pyridyl)azulenes by the Zieglar-Hafner Method2013

    • Author(s)
      Taku Shoji,* Atsuyo Yamamoto, Erika Shimomura, Mitsuhisa Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota and Noboru Morita
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 6 Pages: 638-640

    • DOI

      10.1246/cl.130157

    • NAID

      10031176034

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Azulene-substituted Donor-Acceptor Chromophores Connected by Arylamine Cores2013

    • Author(s)
      Taku Shoji,* Erika Shimomura, Mitsuhisa Maruyama, Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota, Noboru Morita
    • Journal Title

      European Journal of Organic Chemistry

      Volume: なし Issue: 34 Pages: 7785-7799

    • DOI

      10.1002/ejoc.201301006

    • NAID

      120007100275

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Properties and Redox Behavior of Tetracyanobutadiene and Dicyanoquinodimethane Chromophores Bearing Two Azulenyl Substituents2013

    • Author(s)
      Taku Shoji,* Mitsuhisa Maruyama, Erika Shimomura, Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota, Noboru Morita
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 78 Issue: 24 Pages: 12513-12524

    • DOI

      10.1021/jo402104n

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis and Properties of Azulenyltetracyanobutadiene Oligomers connected with Triphenylamine2015

    • Author(s)
      Taku Shoji, Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota
    • Organizer
      平成27年度化学系学協会東北大会
    • Place of Presentation
      弘前大学
    • Year and Date
      2015-09-12
    • Related Report
      2015 Annual Research Report
  • [Presentation] アゾベンゼンに連結したアズレニルテトラシアノブタジエン,ジシアノキノジメタン誘導体の合成研究2014

    • Author(s)
      永井 大地, 丸山 晃史, 庄子 卓
    • Organizer
      第45回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      中部大学 (愛知県春日井市)
    • Year and Date
      2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] アリールアミン類に連結したフェロセニルテトラシアノブタジエンの合成と性質2014

    • Author(s)
      丸山 晃史, 鎌田 夏美, 庄子 卓
    • Organizer
      第45回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      中部大学 (愛知県春日井市)
    • Year and Date
      2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] アリール基に連結したフェロセニルテトラシアノブタジエンの合成と酸化還元的挙動2014

    • Author(s)
      庄子卓, 丸山晃史, 夜久千紗, 鎌田夏美, 奥島鉄雄, 伊東俊司
    • Organizer
      平成26年度化学系学協会東北大会
    • Place of Presentation
      山形大学 (山形県米沢市)
    • Year and Date
      2014-09-20 – 2014-09-21
    • Related Report
      2014 Research-status Report
  • [Presentation] 2-アミノアズレン類の触媒的C-H結合活性化によるアリール化反応の開発2014

    • Author(s)
      庄子卓, 丸山晃史, 藤原優紀, 山本昌, 奥島鉄雄, 伊東俊司
    • Organizer
      平成26年度化学系学協会東北大会
    • Place of Presentation
      山形大学 (山形県米沢市)
    • Year and Date
      2014-09-20 – 2014-09-21
    • Related Report
      2014 Research-status Report
  • [Presentation] アリールアミンオリゴマー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2014

    • Author(s)
      丸山晃史, 庄子卓
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学 (宮城県仙台市)
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] ヘキサフェニルベンゼ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研究2013

    • Author(s)
      丸山 満久, 庄子 卓
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis and Properties of 1,3,5-Tri(1-azulenyl)benzene Derivatives2013

    • Author(s)
      Taku Shoji, Akifumi Maruyama, Erika Shimomura, Mitsuhisa Maruyama, Shunji Ito, Tetsuo Okujima
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      東北大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Donor-Acceptor Type Azulene Derivatives from 1-Pyridylazulenes2013

    • Author(s)
      Taku Shoji, Atsuyo Yamomato, Mitsuhisa Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota, Noboru Morita
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      東北大学
    • Related Report
      2013 Research-status Report
  • [Remarks] 信州大学学術オンラインシステムSOAR

    • URL

      http://soar-rd.shinshu-u.ac.jp/profile/ja.gmShOakh.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] Researchmap

    • URL

      http://researchmap.jp/shoji-azulene

    • Related Report
      2015 Annual Research Report
  • [Remarks] ResearcherID

    • URL

      http://www.researcherid.com/rid/J-5166-2013

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
  • [Remarks] 信州大学 学術情報オンラインシステムSOAR

    • URL

      http://soar-rd.shinshu-u.ac.jp/profile/ja.gmShOakh.html

    • Related Report
      2014 Research-status Report
  • [Remarks] researchmap

    • URL

      http://researchmap.jp/shoji-azulene

    • Related Report
      2014 Research-status Report
  • [Remarks] 信州大学 学術情報オンラインシステムSOAR

    • URL

      http://soar-rd.shinshu-u.ac.jp/profile/ja.gmShOakh.html

    • Related Report
      2013 Research-status Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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