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Synthesis and properties of cyclo[n]pyrroles based on bipyrrole framework

Research Project

Project/Area Number 24750041
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

OKUJIMA TETSUO  愛媛大学, 理工学研究科, 准教授 (60359924)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2012: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords有機化学 / 構造有機化学 / 有機合成 / 芳香族化合物 / ポルフィリノイド / ポルフィリン / 近赤外色素 / 複素環 / 近赤外吸収色素
Research Abstract

Fused-ring-expanded porphyrinoids with no meso-carbon atoms: Cyclo[8]isoindole and cyclo[8]acenaphthopyrroles were successively synthesized based on the oxidative coupling of a bicyclo[2.2.2]octadiene(BCOD)-fused 2,2'-bipyrrole followed by a retro Diels-Alder reaction of BCOD-fused cyclo[8]pyrrole and the oxidative coupling of a 2,2'-bi(acenaphthopyrrole). The X-ray structure of cyclo[8]pyrroles has a saddle-shaped geometry. Key trends in the optical spectra of ring annelated cyclo[8]pyrroles are identified based on an analysis of MCD spectral measurements and the results of TD-DFT calculations.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (18 results)

All 2014 2013 2012

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (14 results) (of which Invited: 1 results)

  • [Journal Article] Synthesis and Molecular Structure of Cyclo[8](9,10-dihydro-9,10-anthraceno)pyr role2014

    • Author(s)
      奥島鉄雄, 安藤千恵, 森重樹, 中江隆博, 山田容子, 宇野英満
    • Journal Title

      Heterocycles

      Volume: 88 Pages: 417-424

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and molecular structure of cyclo[8](9,10-dihydro-9,10-anthraceno)pyrrole2014

    • Author(s)
      Tetsuo Okujima, Chie Ando, Shigeki Mori, Takahiro Nakae, Hiroko Yamada, Hidemitsu Uno
    • Journal Title

      Heterocycles

      Volume: 88 Issue: 1 Pages: 417-424

    • DOI

      10.3987/com-13-s(s)42

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Acenaphthylene-fused cyclo[8]pyrroles with intense NIR region absorption bands2013

    • Author(s)
      奥島鉄雄, 安藤千恵, Mack John, 森重樹, 久木一朗, 中江隆博, 山田容子, 小原敬士, 小林長夫, 宇野英満
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Pages: 13970-13978

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Azulene-Substituted Thiophenes, Terthiophenes and Dithienothiphenes2012

    • Author(s)
      奥島鉄雄, 戸田晃子, 宮下洋子, 埜下歩, 山田容子, 小野昇, 宇野英満
    • Journal Title

      Heterocycles

      Volume: 86 Pages: 637-648

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Presentation] β-アルキル置換シクロ[n]ピロールの合成2014

    • Author(s)
      松本宏樹, 森重樹, 中江隆博, 宇野英満, 奥島鉄雄
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋(名古屋大学)
    • Related Report
      2013 Final Research Report
  • [Presentation] シクロ[8]ピロール類の合成2014

    • Author(s)
      奥島鉄雄, 安藤千恵, 松本宏樹, 中村純, 森重樹, 中江隆博, 宇野英満
    • Organizer
      第4回分子アーキテクトニクス研究会
    • Place of Presentation
      東京(東京大学山上会館)
    • Related Report
      2013 Final Research Report
  • [Presentation] シクロ[8]ピロール類の合成2014

    • Author(s)
      奥島鉄雄・安藤千恵・松本宏樹・中村 純・森 重樹・中江隆博・宇野英満
    • Organizer
      第4回分子アーキテクトニクス研究会
    • Place of Presentation
      東京(東京大学山上会館)
    • Related Report
      2013 Annual Research Report
  • [Presentation] β-アルキル置換シクロ[n]ピロールの合成2014

    • Author(s)
      松本宏樹・森 重樹・中江隆博・宇野英満・奥島鉄雄
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋(名古屋大学)
    • Related Report
      2013 Annual Research Report
  • [Presentation] π拡張シクロ[n]ピロールの合成2013

    • Author(s)
      奥島鉄雄
    • Organizer
      2013年日本化学会中国四国支部大会
    • Place of Presentation
      東広島(広島大学)(若手特別講演)
    • Related Report
      2013 Final Research Report
  • [Presentation] Polycyclic Aromatic-Fused Cyclo[n]pyrroles with Intense NIR Region Absorption Bands2013

    • Author(s)
      奥島鉄雄, 安藤千恵, 森重樹, 中江隆博, 宇野英満
    • Organizer
      15^<th> International Symposium on Novel Aromatic Compounds (ISNA-15)
    • Place of Presentation
      台北(台湾)
    • Related Report
      2013 Final Research Report
  • [Presentation] π拡張シクロ[n]ピロールの合成2013

    • Author(s)
      奥島鉄雄
    • Organizer
      2013年日本化学会中国四国支部大会(若手特別講演)
    • Place of Presentation
      東広島(広島大学)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Polycyclic Aromatic-Fused Cyclo[n]pyrroles with Intense NIR Region Absorption Bands2013

    • Author(s)
      奥島鉄雄・安藤千恵・森 重樹・中江隆博・宇野英満
    • Organizer
      15th International Symposium on Novel Aromatic Compounds (ISNA-15)
    • Place of Presentation
      台北(台湾)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 多環式芳香族縮環シクロ[8]ピロールの合成と物性2012

    • Author(s)
      安藤千恵, 松本直樹, 森重樹, 小原敬士, 中江隆博, 宇野英満, 奥島鉄雄
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都(京都テルサ)
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of π-Expanded Cyclo[8]pyrroles2012

    • Author(s)
      奥島鉄雄, 安藤千恵, 松本直樹, 森重樹, Jin Guangnan, 山田容子, 中江隆博, 小原敬士, 宇野英満
    • Organizer
      Seventh International Conference on Porphyrins and Phthalocyanines (ICPP-7)
    • Place of Presentation
      チェジュ(韓国)
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis and Properties ofβ-Substituted Cyclo[8]pyrroles2012

    • Author(s)
      松本直樹, 安藤千恵, 小原敬士, 森重樹, 中江隆博, 宇野英満, 奥島鉄雄
    • Organizer
      Seventh International Conference on Porphyrins and Phthalocyanines (ICPP-7)
    • Place of Presentation
      チェジュ(韓国)
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of pi-Expanded Cyclo[8]pyrroles2012

    • Author(s)
      奥島鉄雄・安藤千恵・松本直樹・森 重樹・Jin Guangnan・山田容子・中江隆博・小原敬士・宇野英満
    • Organizer
      Seventh International Conference on Porphyrins and Phthalocyanines (ICPP-7)
    • Place of Presentation
      チェジュ(韓国)
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis and Properties of beta-Substituted Cyclo[8]pyrroles2012

    • Author(s)
      松本直樹・安藤千恵・小原敬士・森 重樹・中江隆博・宇野英満・奥島鉄雄
    • Organizer
      Seventh International Conference on Porphyrins and Phthalocyanines (ICPP-7)
    • Place of Presentation
      チェジュ(韓国)
    • Related Report
      2012 Research-status Report
  • [Presentation] 多環式芳香族縮環シクロ[8]ピロールの合成と物性2012

    • Author(s)
      安藤千恵・松本直樹・森 重樹・小原敬士・中江隆博・宇野英満・奥島鉄雄
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都(京都テルサ)
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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