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Development of dynamic pi systems and their functions based on the conformational flexibility and the aromaticity switching

Research Project

Project/Area Number 24750038
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

SAITO Shohei  名古屋大学, 物質科学国際研究センター, 助教 (30580071)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2014: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords芳香族性 / 固体物性 / π共役系 / ホウ素 / ナノグラフェン / 動くπ共役系 / コンフォメーション変化 / 多重発光特性 / 可視化技術 / 構造柔軟性 / 環境応答性 / 応力センサー / メカノクロミズム / 骨格柔軟性 / 動的物性 / 反転障壁 / 励起状態 / πスタッキング / 高圧化学
Outline of Final Research Achievements

We have established efficient syntheses of a series of pi-conjugated molecules that change their aromaticity depending on external stimuli, and that, at the same time, form columnar packing structures in the solid state.
On the other hand, we also developed a chemistry of boron-doped nanographene, in which a boron atom is surrounded by polycyclic aromatic systems.
For both systems, the molecule change their conformation in the solid state due to their high molecular flexibility. The dynamic change of packing structure would be the key to switch solid-state properties of pi-electron systems in a reversible manner.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (53 results)

All 2015 2014 2013 2012 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results,  Acknowledgement Compliant: 2 results) Presentation (32 results) (of which Invited: 6 results) Book (1 results) Remarks (4 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Highly Bent Crystals Formed by Restrained π-Stacked Columns Connected via Alkylene Linkers with Variable Conformations2015

    • Author(s)
      C.-M. Chou, S. Nobusue, S. Saito, D. Inoue, D. Hashizume, S. Yamaguchi
    • Journal Title

      Chem. Sci.

      Volume: 6 Issue: 4 Pages: 2354-2359

    • DOI

      10.1039/c4sc03849e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Photodissociation of B–N Lewis Adducts: A Partially Fused Trinaphthylborane with Dual Fluorescence2014

    • Author(s)
      Kyohei Matsuo, Shohei Saito, Shigehiro Yamaguchi
    • Journal Title

      Journal of American Chemical Society

      Volume: 136 Issue: 36 Pages: 12580-12583

    • DOI

      10.1021/ja506980p

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Heterotriangulenes π-Expanded at Bridging Positions2014

    • Author(s)
      Chih-Ming Chou, Shohei Saito, Shigehiro Yamaguchi
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 11 Pages: 2868-2871

    • DOI

      10.1021/ol501004g

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hybridization of a Flexible Cyclooctatetraene Core and Rigid Aceneimide Wings for Multi-Luminescent Flapping π Systems2014

    • Author(s)
      Chunxue Yuan, Shohei Saito(*), Cristopher Camacho, Tim Kowalczyk, Stephan Irle(*), Shigehiro Yamaguchi(*)
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 8 Pages: 2193-2200

    • DOI

      10.1002/chem.201303955

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] A pi-Conjugated System with Flexibility and Rigidity that Shows Environment-Dependent RGB Luminescence2013

    • Author(s)
      Chunxue Yuan, Shohei Saito(*), Cristopher Camacho, Stephan Irle(*), Ichiro Hisaki, Shigehiro Yamaguchi(*)
    • Journal Title

      Journal of the American Chemistry Society

      Volume: 135 Issue: 24 Pages: 8842-8845

    • DOI

      10.1021/ja404198h

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Distinct responses to mechanical grinding and hydrostatic pressure in luminescent chroism of tetrathiazolythiophene2013

    • Author(s)
      K. Nagura, S. Saito, H. Yusa, H. Yamawaki, H. Fujihisa, H. Sato, Y. Shimoikeda, S. Yamaguchi
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 28 Pages: 10322-10325

    • DOI

      10.1021/ja4055228

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Thermal 8pi Electrocyclic Reaction of Heteroarene Tetramers: New Efficient Access to pi-Extended Cyclooctatetraenes2013

    • Author(s)
      Kazuhiro Mouri, Shohei Saito, Ichiro Hisaki, Shigehiro Yamaguchi(*)
    • Journal Title

      Chemical Science

      Volume: 4 Issue: 12 Pages: 4465-4469

    • DOI

      10.1039/c3sc52232f

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Sequential Electrophilic and Photochemical Cyclizations from Bis(bithienyl)acetylene to a Tetrathienonaphthalene Core2013

    • Author(s)
      Chuandong Dou, Shohei Saito, Libin Gao, Naoki Matsumoto, Takashi Karasawa, Hongyu Zhang, Aiko Fukazawa, Shigehiro Yamaguchi
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 1 Pages: 80-83

    • DOI

      10.1021/ol303107y

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Borylated Dibenzoborepin Synthesized via Skeletal Rearrangement and its Photochromism Based on Bora-Nazarov Cyclization2013

    • Author(s)
      Azusa Iida, Shohei Saito, Takahiro Sasamori, Shigehiro Yamaguchi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 13 Pages: 3760-3764

    • DOI

      10.1002/anie.201210236

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] S-Pechmann Dye: A Thiolactone-Containing Organic Dye with Pronounced Electron-Accepting Character and Its Solid-State Photophysical Properties2013

    • Author(s)
      Aiko Fukazawa, Makoto Adachi, Ken Nakakura, Shohei Saito, Shigehiro Yamaguchi
    • Journal Title

      Chemical Communications

      Volume: 49 Issue: 64 Pages: 7117-7117

    • DOI

      10.1039/c3cc41007b

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluorescent Modular Boron Systems based on NNN- and ONO-Tridentate Ligands: Self-Assembly and Cell Imaging2013

    • Author(s)
      C. Glotzbach, U. Kauscher, J. Voskuhl, N. S. Kehr, M. Stuart, R. Fröhlich, H. Galla, B. J. Ravoo, K. Nagura, S. Saito, S. Yamaguchi, E.-U. Würthwein
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 9 Pages: 4410-4418

    • DOI

      10.1021/jo4003745

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Highly Flexible π-Expanded Cyclooctatetraenes: Cyclic Thiazole Tetramers with Head-to-Tail Connection2012

    • Author(s)
      Kazuhiro Mouri, Shohei Saito, Shigehiro Yamaguchi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 51 Issue: 24 Pages: 5971-5975

    • DOI

      10.1002/anie.201201265

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Polycyclicπ-Electron System with Boronat Its Center2012

    • Author(s)
      Shohei Saito, Kyohei Matsuo, and Shigehiro Yamaguchi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Issue: 22 Pages: 9130-9133

    • DOI

      10.1021/ja3036042

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] N-Heterocyclic Carbene Boranes as Electron-Donating and Electron-Accepting Components of p-Conjugated Systems2012

    • Author(s)
      名倉和彦, 齊藤尚平, Roland Frohlich, Frank Glorius, 山口茂弘
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 51 Issue: 31 Pages: 7762-7766

    • DOI

      10.1002/anie.201204050

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 中央に2つのホウ素をドープしたナノグラフェンの還元特性2015

    • Author(s)
      大角真一朗,Chuangdong Dou,松尾恭平,齊藤尚平,山口茂弘
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ホウ素ドープグラフェンナノリボン (B-GNR) の精密合成,電子構造,ルイス酸性2015

    • Author(s)
      齊藤尚平,川井茂樹,大角真一朗,Adam Foster,Meyer Ernst,山口茂弘
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 含ホウ素π共役系と柔軟なπ共役系の最新展開2014

    • Author(s)
      齊藤尚平
    • Organizer
      関西学院大学理工学部講演会・第55回関学有機化学セミナー
    • Place of Presentation
      関西学院大学
    • Year and Date
      2014-12-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] ホウ素-窒素配位結合を有するルイス酸塩基錯体の光解離2014

    • Author(s)
      松尾恭平,齊藤尚平,山口茂弘
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部市文化会館
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ホウ素を含む多環式π共役化合物の両極性電荷輸送特性2014

    • Author(s)
      松尾恭平,齊藤尚平,山口茂弘
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Environment-Dependent Three-Color Emissions of a Flexible “Bentacene”2014

    • Author(s)
      ○Chigusa Mori, Chunxue Yuan, Shohei Saito, Cristopher Camacho, Stephan Irle, and Shigehiro Yamaguchi
    • Organizer
      統合物質創製化学推進事業, 第3回国際シンポジウム
    • Place of Presentation
      九州大学, 西新プラザ
    • Related Report
      2013 Research-status Report
  • [Presentation] Flexible-Rigid Hybrid π Systems that Show Environment-Dependent Multi-Luminescence for Materials Imaging Technique2014

    • Author(s)
      ○齊藤 尚平
    • Organizer
      The 391st MANA Seminar
    • Place of Presentation
      物質・材料研究機構, MANA
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 異方的に圧縮可能なチャネル状空間の創出を目指した非平面π共役分子の集積構造の構築2014

    • Author(s)
      ○信末俊平, 齊藤尚平, 毛利和弘, 山口茂弘
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 柔軟なπ共役骨格の動きを鍵とした機能性有機材料の開発2014

    • Author(s)
      ○齊藤尚平
    • Organizer
      日本化学会第94春季年会 若い世代の特別講演
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 「π電子系を動かす」技術に基づく新規機能材料の創出2014

    • Author(s)
      ○齊藤尚平
    • Organizer
      日本化学会第94春季年会 社会の持続的発展のための分子技術
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 中央に8員環をもつ柔軟なアセン類縁体の環境依存性3色発光2014

    • Author(s)
      ○森 千草, 齊藤尚平, Yuan Chuxue, Cristopher Camacho, Stephan Irle, 山口茂弘
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Flexible pi-Conjugated Systems for Dynamic Properties2013

    • Author(s)
      ○Shohei Saito
    • Organizer
      JST CREST Nagoya Workshop 2013 “Advanced pi-Electron Materials: Elaborated Design toward New Function”
    • Place of Presentation
      名古屋大学野依記念研究館
    • Related Report
      2013 Research-status Report
  • [Presentation] 柔軟な非平面積層型π電子系の静水圧下における可逆な異方的収縮2013

    • Author(s)
      ○齊藤 尚平・信末 俊平・毛利 和弘・藤原 武徳・佐伯 昭紀 関 修平・藤久 裕司・山脇 浩・山口 茂弘
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学創立100周年記念会館
    • Related Report
      2013 Research-status Report
  • [Presentation] 柔軟なπ共役骨格を基盤とした液晶化合物の光誘起相転移2013

    • Author(s)
      ○津坂 英里・袁 春雪・齊藤 尚平・山口 茂弘
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学創立100周年記念会館
    • Related Report
      2013 Research-status Report
  • [Presentation] 柔軟な分子骨格をもつ有機π電子系の静水圧下における可逆な異方的収縮2013

    • Author(s)
      ○齊藤尚平 信末俊平 毛利和弘 藤原武徳 佐伯昭紀 関修平 藤久裕司 山脇浩 山口茂弘
    • Organizer
      第54回高圧討論会
    • Place of Presentation
      朱鷺メッセ 新潟コンベンションセンター
    • Related Report
      2013 Research-status Report
  • [Presentation] 発光性有機π電子系のメカノクロミズムにおけるすり潰しと静水圧の区別2013

    • Author(s)
      ○齊藤尚平 名倉和彦 遊佐斉 山脇浩 藤久裕司 佐藤寛泰 下池田勇一 山口茂弘
    • Organizer
      第54回高圧討論会
    • Place of Presentation
      朱鷺メッセ 新潟コンベンションセンター
    • Related Report
      2013 Research-status Report
  • [Presentation] 柔軟なπ共役分子の動きに基づく機能発現2013

    • Author(s)
      ○齊藤 尚平
    • Organizer
      第9回有機元素化学セミナー
    • Place of Presentation
      京都大学化学研究所
    • Related Report
      2013 Research-status Report
  • [Presentation] シクロオクタテトラエンで架橋したV字型白金二核錯体の合成2013

    • Author(s)
      ○吉川利樹,袁春雪,齊藤尚平,山口茂弘
    • Organizer
      第10回有機元素化学セミナー
    • Place of Presentation
      京都大学化学研究所
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Flexible π-Conjugated Systems for Dynamic Properties2013

    • Author(s)
      ○齊藤 尚平
    • Organizer
      感応性化学種が拓く新物質科学 若手国際シンポジウム
    • Place of Presentation
      TOKOホテル(五反田)
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Hybridization of Flexibility and Rigidity for the Creation of Functional Materials2013

    • Author(s)
      ○齊藤 尚平
    • Organizer
      グリーン元素科学 国際シンポジウム
    • Place of Presentation
      岡山理科大学
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 圧縮可能なチャネル状空間を指向した柔軟な非平面π共役分子の集積構造の構築2013

    • Author(s)
      ○信末俊平,齊藤尚平,毛利和弘,山口茂弘
    • Organizer
      第8回有機π電子系シンポジウム
    • Place of Presentation
      高崎ビューホテル, 群馬
    • Related Report
      2013 Research-status Report
  • [Presentation] 単一発光団によるRGB発光の実現2013

    • Author(s)
      齊藤 尚平・YUAN, Chunxue・CAMACHO, Cristopher・KOWALCZYK, Tim・IRLE, Stephan・山口 茂弘
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 長鎖アルコキシル置換ホウ素ドープナノグラフェンの合成2013

    • Author(s)
      大角 真一朗・DOU, Chuandong・松尾 恭平・齊藤 尚平・山口 茂弘
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 非平面かつ柔軟なシクロオクタテトラエンを基本骨格とするカラムナー液晶2013

    • Author(s)
      吉村 柾彦・毛利 和弘・齊藤 尚平・山口 茂弘
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] チアゾール4量体の熱的電子環状反応2013

    • Author(s)
      毛利 和弘・齊藤 尚平・山口 茂弘
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 圧力下におけるπ電子系の化学:静水圧と機械的すり潰しの区別2013

    • Author(s)
      名倉 和彦・齊藤 尚平・遊佐 斉・山脇 浩・藤久 裕司・佐藤 寛泰・下池田 勇一・山口 茂弘
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] ノルボルナジエン縮環ポルフィリノイドの合成2013

    • Author(s)
      吉川 利樹・齊藤 尚平・山口 茂弘
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] S-ペックマン色素:高い電子受容性をもつ新奇な色素骨格の開発2013

    • Author(s)
      安達 誠・深澤 愛子・中倉 健・齊藤 尚平・山口 茂弘
    • Organizer
      日本化学会第93春期年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] ホウ素ドープナノグラフェンの有機化学合成2013

    • Author(s)
      齊藤 尚平,Chuandong Dou,大角 真一朗,山口 茂弘
    • Organizer
      応用物理学会春季講演会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] π電子系を広げる・並べる・曲げる・動かす2013

    • Author(s)
      齊藤 尚平
    • Organizer
      東京大学大学院工学系研究科 化学生命工学専攻 談話会
    • Place of Presentation
      東京大学本郷キャンパス
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] π電子系を動かす ~柔軟な分子骨格を活かした機能創出~2013

    • Author(s)
      齊藤 尚平
    • Organizer
      立命館大学薬学部 超分子創製化学セミナー
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Bottom-up Organic Synthesis of Boron-Doped Nanographenes2012

    • Author(s)
      Shohei Saito, Chuandong Dou, Kyohei Matsuo, Shigehiro Yamaguchi
    • Organizer
      The Seventh International Forum on Chemisty of Functional Organic Chemicals
    • Place of Presentation
      東京大学弥生キャンパス
    • Related Report
      2012 Research-status Report
  • [Book] 「化学」2014年5月号解説記事:π共役骨格を動かして機能を発現する2014

    • Author(s)
      ○齊藤尚平, 山口茂弘
    • Total Pages
      6
    • Publisher
      化学同人
    • Related Report
      2013 Research-status Report
  • [Remarks] 名古屋大学理学研究科山口研究室

    • URL

      http://orgreact.chem.nagoya-u.ac.jp/Home.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 名古屋大学理学研究科物質理学専攻化学系 機能有機化学研究室 助教 齊藤尚平

    • URL

      http://orgreact.chem.nagoya-u.ac.jp/Saito-CV.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 独立行政法人 科学技術振興機構 さきがけ「分子技術と新機能創出」領域 齊藤尚平

    • URL

      http://www.jst.go.jp/presto/moltech/researcher/0105saito/index.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 所属研究室の個人紹介ページ

    • URL

      http://orgreact.chem.nagoya-u.ac.jp/Saito-CV.html

    • Related Report
      2012 Research-status Report
  • [Patent(Industrial Property Rights)] π共役化合物、π共役化合物を用いた接着剤、接着剤の使用方法、接合部の剥離方法、及びπ共役化合物の製造方法2014

    • Inventor(s)
      齊藤尚平, 山口茂弘, 渡辺淳, 小谷真央
    • Industrial Property Rights Holder
      齊藤尚平, 山口茂弘, 渡辺淳, 小谷真央
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-032173
    • Filing Date
      2014-02-21
    • Related Report
      2013 Research-status Report
  • [Patent(Industrial Property Rights)] π電子系化合物及び硬化反応可視化剤2013

    • Inventor(s)
      齊藤尚平、山口茂弘
    • Industrial Property Rights Holder
      齊藤尚平、山口茂弘
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-257581
    • Filing Date
      2013-12-13
    • Related Report
      2013 Research-status Report

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

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