Development of aromatic/antiaromatic dehydroannulenes aiming at the rational tuning of the electronic properties

2012 Fiscal Year Final Research Report

• Project/Area Number: 23750033
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Gunma University
• Principal Investigator: KATO Shin-ichiro 群馬大学, 大学院・工学研究科, 助教 (70586792)
• Project Period (FY): 2011 – 2012
• Keywords: デヒドロアヌレン / パイ電子系 / 超分子構造 / 反芳香族性

Research Abstract

In this study, dehydroannulenes annulated at the 9,10-positions of tetraalkoxyphenanthrene have been designed and synthesized, and their various properties have been investigated in detail. Various spectroscopic studies and theoretical calculations clearly indicated that the annulation at the 9,10-positions of phenanthrene into a dehydroannulene ring enhances the tropicities and decreases the HOMO-LUMO gaps as compared to the benzannulation. Dehydro[12]- and [18]annulenes produced1D self-assembling clusters with high aspect ratios, which differed in the morphology and crystallinity depending on the topology of the annulene ring and the length of appended chains. Moreover, [12]- and [18]annulenes formed liquid crystals due to the phase separation facilitated by the flexible decyloxy side chains.

Research Products

• [Journal Article] Tetraalkoxyphenanthrene-Fused Dehydroannulenes: Synthesis, Electronic, Optical, and Electrochemical Properties, and Self-Assembly (2013)
  • Author(s): Shin-ichiro Kato, Nobutaka Takahashi, Hidekazu Tanaka, Atsushi Kobayashi, Toshitada Yoshihara, Seiji Tobita, Takeshi Yamanobe, Hiroki Uehara, Yosuke Nakamura
  • Journal Title: Chem. Eur. J
  • Peer Reviewed
• [Journal Article] Bicarbazoles: Systematic Structure-Property Investigations on a Series of Conjugated Carbazole Dimers (2012)
  • Author(s): Shin-ichiro Kato, Hiroto Noguchi, Atsushi Kobayashi, Toshitada Yoshihara, Seiji Tobita, Yosuke Nakamura
  • Journal Title: J. Org. Chem Volume: Vol.77 Pages: 9120-9133
  • Peer Reviewed
• [Journal Article] SeijiTobita, Yosuke Nakamura, π-Extended Thiadiazoles Fused with Thienopyrrole or Indole Moieties: Synthesis, Structures, and Properties (2012)
  • Author(s): Shin-ichiro Kato, Takayuki Furuya, Atsushi Kobayashi, Masashi Nitani, Yutaka Ie, Yoshio Aso, Toshitada Yoshihara
  • Journal Title: J. Org. Chem Volume: Vol.77 Pages: 7595-7606
  • Peer Reviewed
• [Journal Article] Synthesis and Electronic,Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles (2012)
  • Author(s): Shin-ichiro Kato, Satoru Shimizu, Hiroaki Taguchi, Atsushi Kobayashi, Seiji Tobita, Yosuke Nakamura
  • Journal Title: J. Org. Chem Volume: Vol.77 Pages: 3222-3232
  • Peer Reviewed
• [Presentation] テトライン架橋を有するデヒドロアヌレン類の合成と物性 (2013)
  • Author(s): 高橋伸尚,加藤真一郎,中村洋介
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 滋賀
  • Year and Date: 2013-03-24
• [Presentation] 高度に縮合共役系が拡張したチアジアゾール誘導体の光・電子機能と多様な集積構造 (2013)
  • Author(s): 加藤真一郎
  • Organizer: 産総研講演会
  • Place of Presentation: 筑波(依頼講演)
  • Year and Date: 2013-01-20
• [Presentation] 集積分子機能発現を指向した縮合共役電子系化合物の合成と性質 (2012)
  • Author(s): 加藤真一郎
  • Organizer: 九州大学先導研講演会
  • Place of Presentation: 福岡(依頼講演)
  • Year and Date: 2012-12-03
• [Presentation] 高度に縮合共役系が拡張したチアジアゾール誘導体の合成と昨日開拓 (2012)
  • Author(s): 加藤真一郎
  • Organizer: 第1回近未来材料研究会
  • Place of Presentation: 福岡(依頼講演)
  • Year and Date: 2012-12-01
• [Presentation] フェナントレンが縮環したデヒドロ[12]および[18]アヌレンの合成と自己集合挙動 (2012)
  • Author(s): 高橋伸尚,加藤真一郎,中村洋介
  • Organizer: 第23回基礎有機化学討論会
  • Place of Presentation: 京都
  • Year and Date: 2012-09-19
• [Presentation] フェナントレンが縮環したデヒドロ[12]および[18]アヌレンの合成と自己集合挙動 (2012)
  • Author(s): 高橋伸尚,加藤真一郎,中村洋介
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 東京
  • Year and Date: 2012-03-26
• [Presentation] フェナントレンが縮環したデヒドロ[12]および[18]アヌレンの反芳香族性・芳香族性 (2011)
  • Author(s): 高橋伸尚,加藤真一郎,中村洋介
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: 京都
  • Year and Date: 2011-09-21
• [Remarks]
  • URL: http://nakamuralab.dept.eng.gunma-u.ac.jp/