• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

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

Research Project

Project/Area Number 23750033
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionGunma 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
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsデヒドロアヌレン / パイ電子系 / 超分子構造 / 反芳香族性 / 共役環状分子 / 超分子化学 / アセチレン
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.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (26 results)

All 2013 2012 2011 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (17 results) (of which Invited: 3 results) Remarks (1 results)

  • [Journal Article] Tetraalkoxyphenanthrene-Fused Dehydroannulenes: Synthesis, Electronic, Optical, and Electrochemical Properties, and Self-Assembly2013

    • 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Tetraalkoxyphenanthrene-Fused Dehydroannulenes: Synthesis, Electronic, Optical, and Electrochemical Properties, and Self-Assembly2013

    • 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.

      Volume: 未定

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bicarbazoles: Systematic Structure-Property Investigations on a Series of Conjugated Carbazole Dimers2012

    • 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] SeijiTobita, Yosuke Nakamura, π-Extended Thiadiazoles Fused with Thienopyrrole or Indole Moieties: Synthesis, Structures, and Properties2012

    • 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Electronic,Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles2012

    • 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bicarbazoles: Systematic Structure-Property Investigations on a Series of Conjugated Carbazole Dimers2012

    • Author(s)
      Shin-ichiro Kato, Hiroto Noguchi, Atsushi Kobayashi, Toshitada Yoshihara, Seiji Tobita, Yosuke Nakamura
    • Journal Title

      J. Org. Chem.

      Volume: 77 Issue: 20 Pages: 9120-9133

    • DOI

      10.1021/jo3016538

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] π-Extended Thiadiazoles Fused with Thienopyrrole or Indole Moieties: Synthesis, Structures, and Properties2012

    • Author(s)
      S.-i. Kato, T. Furuya, A. Kobayashi, M. Nitani, Y. Ie, Y. Aso, T. Yoshihara, S. Tobita, Y. Nakamura
    • Journal Title

      J. Org. Chem.

      Volume: 77 Issue: 17 Pages: 7595-7606

    • DOI

      10.1021/jo301458m

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles2012

    • Author(s)
      Shin-ichiro Kato, Satoru Shimizu, Hiroaki Taguchi, Atsushi Kobayashi, Seiji Tobita, Yosuke Nakamura
    • Journal Title

      J. Org. Chem.

      Volume: 77 Issue: 7 Pages: 3222-3232

    • DOI

      10.1021/jo202625p

    • Related Report
      2012 Annual Research Report
    • 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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
      慶応義塾大学(東京都)
    • Related Report
      2011 Research-status Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
      日本化学会第5回関東支部大会
    • Place of Presentation
      東京農工大学(東京都)
    • Related Report
      2011 Research-status Report
  • [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
      つくば国際会議場(茨城県)
    • Related Report
      2011 Research-status Report
  • [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)
      加藤真一郎,高橋伸尚,中村洋介
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      ホテルアウィーナ大阪(大阪府)
    • Related Report
      2011 Research-status Report
  • [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

    • 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
      立命館大学(滋賀)
    • Related Report
      2012 Annual Research Report
  • [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

    • 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
      京都テルサ(京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] フェナントレンが縮環したデヒドロ[12]および[18]アヌレンの合成と反芳香族性・芳香族性

    • 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
      つくば国際会議場(筑波)
    • Related Report
      2012 Annual Research Report
  • [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機能開拓

    • Author(s)
      加藤真一郎
    • Organizer
      第1回近未来材料研究会
    • Place of Presentation
      ホテル福岡ガーデンパレス(福岡)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [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

    • Author(s)
      加藤真一郎
    • Organizer
      九州大学先導研講演会
    • Place of Presentation
      九州大学(福岡)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [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

    • Author(s)
      加藤真一郎
    • Organizer
      産総研講演会
    • Place of Presentation
      産総研(筑波)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Remarks]

    • URL

      http://nakamuralab.dept.eng.gunma-u.ac.jp/

    • Related Report
      2012 Final Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi