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

Research Project

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
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機半導体 / 共役 / 構造化学 / 芳香族化合物 / ケイ素 / 構造・機能材料 / 合成化学 / 半導体物性 / 結晶工学 / 光物性
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.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (44 results)

All 2014 2013 2012 2011 2010 Other

All Journal Article (19 results) (of which Peer Reviewed: 18 results) Presentation (19 results) (of which Invited: 1 results) Book (1 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 1 results)

  • [Journal Article] Double-Pillaring Strategy for Silacyclophanes: Synthesis and Structures of Disilanyl Double-Pillared Bisanthracenes (vol 6, pg, 2011)2014

    • Author(s)
      Nakanishi, Waka; Hitosugi, Shunpei; Shimada, Yusuke; et al.
    • Journal Title

      Chemistry-an Asian Journal

      Volume: 9 Issue: 2 Pages: 398-398

    • DOI

      10.1002/asia.201301579

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [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) Issue: 6 Pages: 1177-1181

    • DOI

      10.1002/asia.201300098

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [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) Issue: 36 Pages: 4963-4965

    • DOI

      10.1016/j.tetlet.2013.07.025

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iridium-catalyzed direct borylation of phenacenes2012

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

      Isobe, H. Tetrahedron Lett

      Volume: 53 (9) Issue: 9 Pages: 1180-1182

    • DOI

      10.1016/j.tetlet.2011.12.106

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [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) Issue: 6 Pages: 1636-1639

    • DOI

      10.1021/ol3003964

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [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) Issue: 7 Pages: 1550-1552

    • DOI

      10.1002/asia.201200187

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [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)

    • Related Report
      2013 Final Research Report
  • [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) Issue: 9 Pages: 972-973

    • DOI

      10.1246/cl.2012.972

    • NAID

      130004426693

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [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) Issue: 12 Pages: 1652-1654

    • DOI

      10.1246/cl.2012.1652

    • NAID

      10031135782

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [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 Issue: 2 Pages: 554-559

    • DOI

      10.1002/asia.201000543

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [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 Issue: 23 Pages: 5323-5326

    • DOI

      10.1002/anie.201101314

    • NAID

      130004645748

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [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 Issue: 27 Pages: 6048-6051

    • DOI

      10.1002/anie.201102210

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] [6]Cyclo-2,7-naphthylene : A redetermination2011

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

      Acta Crystallogr., Sect.E

      Volume: E67 Issue: 7 Pages: o1762-o1763

    • DOI

      10.1107/s1600536811023427

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [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 Issue: 1 Pages: 5-5

    • DOI

      10.1038/ncomms1505

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Double-pillaring strategy for silacyclophanes : synthesis and structures of disilanyl double-pillared bisanthracenes.2011

    • Author(s)
      Waka Nakanishi, et.al.
    • Journal Title

      Chem.Asian J.

      Volume: 6 Pages: 554-559

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [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) Issue: 40 Pages: 7239-7242

    • DOI

      10.1002/anie.201002432

    • NAID

      130004729335

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [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) Issue: 10 Pages: o2515-o2515

    • DOI

      10.1107/s1600536810035191

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Disilanyl double-pillared bisanthracene : A bipolar carrier transport material for organic light emitting diode devices.2010

    • Author(s)
      Waka Nakanishi, et.al.
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 49 Pages: 7239-7242

    • NAID

      130004729335

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1,8-Diiodoanthracene2010

    • Author(s)
      Waka Nakanishi, et.al.
    • Journal Title

      Acta Crystallogr.Sect.E

      Volume: 66 Pages: 2515-2515

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [Presentation] Construction of Conjugated Cyclic Molecules through Multiple Single Bond Formations2014

    • 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
      Nagoya
    • Related Report
      2013 Annual Research Report
  • [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2014

    • 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
    • Related Report
      2013 Annual Research Report
  • [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2014

    • Author(s)
      中西和嘉,嶋田裕亮,磯部寛之
    • Organizer
      日本化学会年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Annual Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [Presentation] 単結合多重連結による環状共役分子の合成と性質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
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Structural Analysis of Disilanyl Double-Pillared Bisheteroarenes2013

    • Author(s)
      W. Nakanishi, Y. Shimada, and H. Isobe
    • Organizer
      MRS-Japan
    • Place of Presentation
      Yokohama
    • Related Report
      2013 Annual Research Report
  • [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
      東北薬科大学(招待講演)
    • Year and Date
      2011-08-28
    • Related Report
      2011 Annual Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [Presentation] 化学者のだまし絵:「Penroseの階段」分子2011

    • Author(s)
      中西和嘉
    • Organizer
      平成23年度化学系学協会東北大会
    • Place of Presentation
      川内北キャンパス(9.17発表)
    • Related Report
      2011 Annual Research Report
  • [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
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば国際会議場(9.22発表)
    • Related Report
      2011 Annual Research Report
  • [Presentation] [n]シクロ-2,7-ナフチレン:合成と有機ELキャリア輸送層への応用2011

    • Author(s)
      中西和嘉
    • Organizer
      高次π空間の創発と機能開発第4回若手研究会
    • Place of Presentation
      物質・材料研究機構千現地区(11.17発表)
    • Related Report
      2011 Annual Research Report
  • [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
      化学系学協会東北大会
    • Place of Presentation
      岩手大学
    • Year and Date
      2010-09-25
    • Related Report
      2010 Annual Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2013 Final Research Report
  • [Remarks]

    • URL

      http://www.orgchem2.chem.tohoku.ac.jp/Main/Top.html

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.orgchem2.chem.tohoku.ac.jp/Main/Top.html

    • Related Report
      2010 Annual Research Report
  • [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
      特許
    • Acquisition Date
      2012-06-28
    • Related Report
      2013 Final Research Report
    • Overseas
  • [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2010

    • Inventor(s)
      磯部寛之、中西和嘉、吉岡知昭
    • Industrial Property Rights Holder
      国立大学法人東北大学
    • Industrial Property Number
      2010-275387
    • Filing Date
      2010-12-10
    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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