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

2013 Fiscal Year Final Research Report

• Project/Area Number: 24750041
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Ehime 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
• 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

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.

Research Products

• [Journal Article] Synthesis and Molecular Structure of Cyclo[8](9,10-dihydro-9,10-anthraceno)pyr role (2014)
  • 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
  • Peer Reviewed
• [Journal Article] Acenaphthylene-fused cyclo[8]pyrroles with intense NIR region absorption bands (2013)
  • 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
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Azulene-Substituted Thiophenes, Terthiophenes and Dithienothiphenes (2012)
  • 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
  • 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)
  • Year and Date: 20140327-30
• [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)
  • Year and Date: 20140311-12
• [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)
  • Year and Date: 20131116-17
• [Presentation] Polycyclic Aromatic-Fused Cyclo[n]pyrroles with Intense NIR Region Absorption Bands (2013)
  • 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)
  • Year and Date: 20130728-0802
• [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)
  • Year and Date: 20120919-21
• [Presentation] Synthesis of π-Expanded Cyclo[8]pyrroles (2012)
  • 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)
  • Year and Date: 20120701-06
• [Presentation] Synthesis and Properties ofβ-Substituted Cyclo[8]pyrroles (2012)
  • 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)
  • Year and Date: 20120701-06