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2013 Fiscal Year Final Research Report

Development of organic semiconductor based on efficient synthesis of polycyclic aromatic hydrocarbons

Research Project

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Project/Area Number 22550094
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionNational Institute for Materials Science (2013)
Tohoku University (2010-2012)

Principal Investigator

NAKANISHI Waka  独立行政法人物質・材料研究機構, その他部局等, その他 (20401010)

Project Period (FY) 2010-04-01 – 2014-03-31
Keywords有機半導体 / 共役 / 構造化学 / 芳香族化合物 / ケイ素
Research Abstract

Because of the interest in the unique electronic features of molecules with large conjugated structures, synthesis of large polycyclic aromatic hydrocarbons through the expansion of a ring-fused structure has recently been widely studied. On the other hand, in this research, a series of novel, large conjugated cyclic molecules were constructed by connecting small aromatic molecules via (a) C-C or (b) Si-Si single bonds. Through rational design of the angle and connection formed, sheet, tube, and step-like conjugated structures were constructed. As a results a series of new molecules with outstanding characteristics were developed: One of the molecules had an extremely high thermal stability with an enhanced ability to delocalize spin and charge, and it was a good carrier transporter in organic light-emitting diode (OLED) devices.

  • Research Products

    (27 results)

All 2014 2013 2012 2011 2010 Other

All Journal Article (15 results) Presentation (9 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Structural fluctuation of disilanyl double-pillared bisheteroarenes2013

    • Author(s)
      Nakanishi, W.; Shimada, Y.; Isobe, H.
    • Journal Title

      Chem. Asian J.

      Volume: 8 (6) Pages: 1177-1181

    • DOI

      10.1002/asia.201300098

  • [Journal Article] Convergent synthesis of hexameric naphthylene macrocycles with dicarboxylic imide appendages2013

    • Author(s)
      Xue, J. Y.; Nakanishi, W.; Tanimoto, D.; Hara, D.; Nakamura, Y.; Isobe, H.
    • Journal Title

      Tetrahedron Lett.

      Volume: 54 (36) Pages: 4963-4965

    • DOI

      10.1016/j.tetlet.2013.07.025

  • [Journal Article] Iridium-catalyzed direct borylation of phenacenes2012

    • Author(s)
      Hitosugi, S.; Nakamura, Y.; Matsuno, T.; Nakanishi, W.; Isobe, H.
    • Journal Title

      Tetrahedron Lett.

      Volume: 53 (9) Pages: 1180-1182

    • DOI

      10.1016/j.tetlet.2011.12.106

  • [Journal Article] Synthesis of disilanyl double-pillared bisdibenzofuran with a high triplet energy2012

    • Author(s)
      Nakanishi, W.; Shimada, Y.; Taka, H.; Kita, H.; Isobe, H.
    • Journal Title

      Org. Lett.

      Volume: 14 (6) Pages: 1636-1639

    • DOI

      10.1021/ol3003964

  • [Journal Article] Atropisomerism in a belt-persistent nanohoop molecule : Rotational restriction forced by macrocyclic ring strain2012

    • Author(s)
      Hitosugi, S.; Nakanishi, W.; Isobe, H.
    • Journal Title

      Chem. Asian J.

      Volume: 7 (7) Pages: 1550-1552

    • DOI

      10.1002/asia.201200187

  • [Journal Article] 2,11-Dibromo-5,8-dibutyl[4]helicene, Acta Crystallogr2012

    • Author(s)
      Isobe, H.; Matsuno, T.; Hitosugi, S.; Nakanishi, W.
    • Journal Title

      Sect. E : Struct. Rep. Online

      Volume: E68 (4) Pages: o1239

  • [Journal Article] A facile chromatographic method for purification of pinacol boronic esters2012

    • Author(s)
      Hitosugi, S.; Tanimoto, D.; Nakanishi, W.; Isobe, H.
    • Journal Title

      Chem. Lett.

      Volume: (9) Pages: 972-973

    • DOI

      10.1246/cl.2012.972

  • [Journal Article] Flexible silacyclophanes with two tricyclic aromatic units linked by two disilanyl pillars2012

    • Author(s)
      Nakanishi, W.; Kamata, S.; Hitosugi, S.; Isobe, H.
    • Journal Title

      Chem. Lett.

      Volume: 41 (12) Pages: 1652-1654

    • DOI

      10.1246/cl.2012.1652

  • [Journal Article] Double-pillaring strategy for silacyclophanes : Synthesis and structures of disilanyl double-pillared bisanthracenes2011

    • Author(s)
      Nakanishi, W.; Hitosugi, S.; Shimada, Y.; Isobe, H.
    • Journal Title

      Chem. Asian J.

      Volume: 6 (2) Pages: 554-559

    • DOI

      10.1002/asia.201000543

  • [Journal Article] [n]Cyclo-2,7-naphthylenes : Synthesis and isolation of macrocyclic aromatic hydrocarbons having bipolar carrier transport ability2011

    • Author(s)
      Nakanishi, W.; Yoshioka, T.; Taka, H.; Xue, J. Y.; Kita, H.; Isobe, H.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 50 (23) Pages: 5323-5326

    • DOI

      10.1002/anie.201101314

  • [Journal Article] Illusory molecular expression of "Penrose stairs" by an aromatic hydrocarbon2011

    • Author(s)
      Nakanishi, W.; Matsuno, T.; Ichikawa, J.; Isobe, H.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 50 (27) Pages: 6048-6051

    • DOI

      10.1002/anie.201102210

  • [Journal Article] [6]Cyclo-2,7-naphthylene : a redetermination2011

    • Author(s)
      Nakanishi, W.; Xue, J. Y.; Yoshioka, T.; Isobe, H.
    • Journal Title

      Acta Crystallogr., Sect. E : Struct. Rep. Online

      Volume: E67 (7) Pages: o1762-o1763

    • DOI

      10.1107/S1600536811023427

  • [Journal Article] Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes2011

    • Author(s)
      Hitosugi, S.; Nakanishi, W.; Yamasaki, T.; Isobe, H.
    • Journal Title

      Nat. Commun

      Volume: 2 (10)

    • DOI

      10.1038/ncomms1505.

  • [Journal Article] Disilanyl double-pillared bisanthracene : A bipolar carrier transport material for organic light emitting diode devices2010

    • Author(s)
      Nakanishi, W.; Hitosugi, S.; Piskareva, A.; Shimada, Y.; Taka, H.; Kita, H.; Isobe, H.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 (40) Pages: 7239-7242

    • DOI

      10.1002/anie.201002432

  • [Journal Article] 1,8-Diiodoanthrancene2010

    • Author(s)
      Nakanishi, W.; Hitosugi, S.; Piskareva, A.; Isobe, H.
    • Journal Title

      Acta Crystallogr., Sect. E : Struct. Rep. Online

      Volume: E66 (10) Pages: o2515

    • DOI

      10.1107/S1600536810035191

  • [Presentation] シラン二重架橋による複素芳香族化合物二量体の合成と構造解析2014

    • Author(s)
      中西和嘉,嶋田裕亮,磯部寛之
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      20140327-30
  • [Presentation] Synthesis and Structural Analysis of Disilanyl Double-Pillared Bisheteroarenes2014

    • Author(s)
      Waka Nakanishi, Yusuke Shimada, and Hiroyuki Isobe
    • Organizer
      MANA International Symposium 2014
    • Place of Presentation
      Tsukuba
    • Year and Date
      20140305-07
  • [Presentation] Synthesis and Structural Analysis of Disilanyl Double-Pillared Bisheteroarenes2013

    • Author(s)
      W. Nakanishi, Y. Shimada, and H. Isobe
    • Organizer
      23rd Annual Meeting of MRS-Japan 2013
    • Place of Presentation
      Yokohama
    • Year and Date
      20131209-11
  • [Presentation] 非平面環状共役分子の合成と機能2013

    • Author(s)
      中西和嘉
    • Organizer
      高分子学会茨城地区若手の会
    • Place of Presentation
      つくばみらい市
    • Year and Date
      20131007-08
  • [Presentation] Construction of Conjugated Cyclic Molecules through Multiple Single Bond Formations2013

    • Author(s)
      Waka Nakanishi, Tomoaki Yoshioka, Hideo Taka, Jing Yang Xue, Hiroshi Kita, Hiroyuki Isobe
    • Organizer
      第64回コロイドおよび界面化学討論会
    • Place of Presentation
      名古屋
    • Year and Date
      20130918-20
  • [Presentation] ジシラン二重架橋による複素芳香族化合物二量体の合成と構造解析2013

    • Author(s)
      中西和嘉,嶋田裕亮,磯部寛之
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      東京
    • Year and Date
      20130905-07
  • [Presentation] 単結合多重連結による環状共役分子の合成と性質2011

    • Author(s)
      中西和嘉,松野太輔,市川淳士,磯部寛之
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば
    • Year and Date
      20110921-23
  • [Presentation] 単結合多重連結による環状共役構造の構築2011

    • Author(s)
      中西和嘉
    • Organizer
      第10回化学系薬学若手研究者セミナー
    • Place of Presentation
      仙台
    • Year and Date
      2011-08-25
  • [Presentation] ジシラニル二重架橋ビスアントラセン:OLEDデバイスにおける両極性キャリア輸送材料2010

    • Author(s)
      中西和嘉
    • Organizer
      高次π空間の創発と機能開発総括班主催第2回若手研究会
    • Place of Presentation
      つくば
    • Year and Date
      20100715-17
  • [Book] 最短カーボンナノチューブ分子を組上げる:帯状分子のボトムアップ化学合成、現代化学 (5月号)2012

    • Author(s)
      一杉俊平,中西和嘉,磯部寛之
    • Total Pages
      33-38
  • [Remarks]

    • URL

      http://www.nims.go.jp/super/HP/home.htm

  • [Patent(Industrial Property Rights)] 縮退系大環状化合物,並びに,その結 晶及び製造方法2012

    • Inventor(s)
      磯部 寛之,中西 和嘉,吉岡 知昭
    • Industrial Property Rights Holder
      東北大学
    • Industrial Property Rights Type
      公開特許
    • Industrial Property Number
      2012-121861
    • Acquisition Date
      2012-06-28
    • Overseas

URL: 

Published: 2015-07-16  

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