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Chemical synthesis of graphene model molecules with atomic defects

Research Project

Project/Area Number 21685005
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionTohoku University

Principal Investigator

ISOBE Hiroyuki  東北大学, 大学院・理学研究科, 教授 (30302805)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥23,400,000 (Direct Cost: ¥18,000,000、Indirect Cost: ¥5,400,000)
Fiscal Year 2011: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2010: ¥8,060,000 (Direct Cost: ¥6,200,000、Indirect Cost: ¥1,860,000)
Fiscal Year 2009: ¥11,570,000 (Direct Cost: ¥8,900,000、Indirect Cost: ¥2,670,000)
Keywordsπスタック / クリセン / 多環式芳香族化合物 / 有機エレクトロニクス / グラフェン / ナノチューブ / 有機合成 / 帯状分子 / 原子欠損 / だまし絵 / アントラセン
Research Abstract

Recently, the studies for bottom-up production of discrete large π-conjugated molecules are focused much attention. In this research, we designed and synthesized new π-conjugated molecules inspired by new π-conjugated molecular species, "graphene with atomic defects", which had been found by electronic microscope analysis.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (58 results)

All 2013 2012 2011 2010 2009 Other

All Journal Article (27 results) (of which Peer Reviewed: 27 results) Presentation (24 results) Remarks (4 results) Patent(Industrial Property Rights) (3 results) (of which Overseas: 1 results)

  • [Journal Article] 2,11-Dibromo-5,8-dibutyl[4]helicene2012

    • Author(s)
      Isobe Hiroyuki, Matsuno, Taisuke, Hitosugi Shunpei, Nakanishi Waka
    • Journal Title

      Acta Crystallographica Section E: Structure Reports Online

      Volume: E68 Issue: 4 Pages: o1239-o1239

    • DOI

      10.1107/s1600536812013141

    • Related Report
      2011 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
      2011 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
      2011 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
      2011 Final 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
      2011 Annual Research Report 2011 Final 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
      2011 Annual Research Report 2011 Final 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
      2011 Annual Research Report 2011 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
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Electron mobility in a mercury-mediated duplex of triazole-linked DNA (^<TL>DNA)2011

    • Author(s)
      Isobe, H.; Yamazaki, N.; Asano, A.; Fujino, T.; Nakanishi, W.; Seki, S.
    • Journal Title

      Chem.Lett.

      Volume: 40 Issue: 3 Pages: 318-319

    • DOI

      10.1246/cl.2011.318

    • NAID

      130004426164

    • Related Report
      2011 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
      2011 Annual Research Report 2011 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
      2011 Final 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
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nanometer-size fluorous fullerene vesicles in water and on solid surfaces2010

    • Author(s)
      Homma, T.; Harano, K.; I sobe, H; Nakamura, E
    • Journal Title

      Angew. Chem. Int Ed

      Volume: 49(9) Issue: 9 Pages: 1665-1668

    • DOI

      10.1002/anie.200904659

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] In vivo gene delivery by cationic tetraamino fullerene2010

    • Author(s)
      Maeda-Mamiya, R.; Noiri, E.; Isobe, H.; Nakanishi, W.; Okamoto, K.; Doi, K.; Sugaya, T.; Izumi, T.; Homma, T.; Nakamura, E
    • Journal Title

      Proc. Natl. Acad. Sci. U.S.A

      Volume: 107 Issue: 12 Pages: 5339-5344

    • DOI

      10.1073/pnas.0909223107

    • Related Report
      2011 Final 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., et al
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 49 Pages: 7239-7242

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1,8-Diiodoanthrancene2010

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

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

      Volume: E66

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and facile ring expansion of silylenecyclotetrasilane2010

    • Author(s)
      Iwamoto, T., et al
    • Journal Title

      Organometallics

      Volume: 29 Pages: 1869-1872

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)2010

    • Author(s)
      Fujino, T., et al
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 2036-2038

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and structure of stable base-free dialkylsilanimines2010

    • Author(s)
      Iwamoto, T., et al
    • Journal Title

      New J.Chem.

      Volume: 34 Pages: 1637-1645

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reversible aggregation and deaggregation of helicene-grafted chiral silica nanoparticles induced by aromatic solvents2010

    • Author(s)
      An, Z.
    • Journal Title

      Chem.Lett.

      Volume: 39 Pages: 1004-1005

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nanometer-size fluorous fullerene vesicles in water and on solid surfaces2010

    • Author(s)
      Homma, T., et al
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 49 Pages: 1665-1668

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] In vivo gene delivery by cationic tetraamino fullerene2010

    • Author(s)
      Maeda-Mamiya, R., et al
    • Journal Title

      Proc.Natl.Acad.Sci.U.S.A.

      Volume: 107 Pages: 5339-5344

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] In vitro and in vivo gene delivery with tailor-designed aminofullerenes2010

    • Author(s)
      Nakamura, E., et al
    • Journal Title

      Chem.Rec.

      Volume: 10 Pages: 260-270

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nanometer-size fluorous fullerene vesicles in water and on solid surfaces2010

    • Author(s)
      Homma, T., ほか
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 1665-1668

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Concise Synthesis of Halogenated Chrysenes ([4]Phenacenes) That Favor π-Stack Packing in Single Crystals2009

    • Author(s)
      Isobe, H.; Hitosugi, S.; Matsuno, T.; Iwamoto, T.; Ichikawa, J
    • Journal Title

      Org. Lett

      Volume: 11 Issue: 17 Pages: 4026-4028

    • DOI

      10.1021/ol901693y

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Concise synthesis of halogenated chrysenes([4]phenacenes)that favor II-stack packing in single crystals2009

    • Author(s)
      Isobe, H., ほか
    • Journal Title

      Org.Lett. 11

      Pages: 4026-4028

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced electron transfer of nano-hybrids of carbon nanohorns with amino group and tetrabenzoic acid porphyrin in aqueous media2009

    • Author(s)
      Sandanayaka, A., ほか
    • Journal Title

      New J.Chem.

      Pages: 2261-2266

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] ジシラン二重架橋によるカルバゾール二量体の合成2013

    • Author(s)
      鎌田翔,中西和嘉,磯部寛之
    • Organizer
      日本化学会第93回春季年会3A3-50
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-24
    • Related Report
      2011 Final Research Report
  • [Presentation] ジシラン二重架橋によるカルバゾール二量体の合成2012

    • Author(s)
      鎌田翔,中西和嘉,磯部寛之
    • Organizer
      第23回基礎有機化学討論会1P086
    • Place of Presentation
      京都
    • Year and Date
      2012-09-19
    • Related Report
      2011 Final Research Report
  • [Presentation] らせん型最短カーボンナノチューブのボトムアップ化学合成2012

    • Author(s)
      一杉俊平,中西和嘉,山崎孝史,磯部寛之
    • Organizer
      第23回基礎有機化学討論会A07
    • Place of Presentation
      京都
    • Year and Date
      2012-09-19
    • Related Report
      2011 Final Research Report
  • [Presentation] らせん型最短ナノチューブのボトムアップ化学合成2012

    • Author(s)
      一杉俊平,中西和嘉,山崎孝史,磯部寛之
    • Organizer
      第43回フラーレン・ナノチューブ・グラフェン総合シンポジウム1P-31
    • Place of Presentation
      仙台
    • Year and Date
      2012-09-05
    • Related Report
      2011 Final Research Report
  • [Presentation] "Illusory molecular expression of"Penrose stairs" by an aromatic hydrocarbon and dynamic behaviors in solution"2012

    • Author(s)
      Matsuno, T.; Nakanishi, W.; Ichikawa, J.; Isobe, H
    • Organizer
      The Campus Asia Summer School 2012 (O-18)
    • Place of Presentation
      仙台
    • Year and Date
      2012-08-22
    • Related Report
      2011 Final Research Report
  • [Presentation] らせん型最短ナノチューブのボトムアップ化学合成2012

    • Author(s)
      一杉俊平,中西和嘉,山崎孝史,磯部寛之
    • Organizer
      日本化学会第92春期年会4E1-25
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-28
    • Related Report
      2011 Final Research Report
  • [Presentation] 錯視的構造を有する環状多環式芳香族化合物の合成と溶液中での動的挙動2012

    • Author(s)
      松野太輔,中西和嘉,市川淳士,磯部寛之
    • Organizer
      日本化学会第92回春季年会3K2-03
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-27
    • Related Report
      2011 Final Research Report
  • [Presentation] π電子豊富分子の科学2011

    • Author(s)
      磯部寛之
    • Organizer
      第22回万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター(招待講演)
    • Year and Date
      2011-12-19
    • Related Report
      2011 Annual Research Report
  • [Presentation] 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)
      Xue Jing,中西和嘉,吉岡知昭,高秀雄,北弘志,磯部寛之
    • Organizer
      第22回基礎有機化学討論会1P124
    • Place of Presentation
      筑波
    • Year and Date
      2011-09-21
    • Related Report
      2011 Final Research Report
  • [Presentation] 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)
      Xue Jing,中西和嘉,吉岡知昭,高秀雄,北弘志,磯部寛之
    • Organizer
      平成23年度化学系学協会東北大会1P087
    • Place of Presentation
      仙台
    • Year and Date
      2011-09-18
    • Related Report
      2011 Final Research Report
  • [Presentation] 復興マラソン:有機化学研究室の一事例2011

    • Author(s)
      磯部寛之
    • Organizer
      防災・日本再生シンポジウム「東北地方の化学と教育:3.11から189日の歩み」
    • Place of Presentation
      東北大学片平キャンパス,仙台(招待講演)
    • Year and Date
      2011-09-16
    • Related Report
      2011 Annual Research Report
  • [Presentation] 生体内π空間を写しとる人工DNA2011

    • Author(s)
      磯部寛之
    • Organizer
      高次π空間の創発と機能開発第7回公開シンポジウム
    • Place of Presentation
      メルパルク松山
    • Year and Date
      2011-03-13
    • 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における両極性キャリア輸送材料2011

    • Author(s)
      一杉俊平,中西和嘉,アンナピスカリョーバ,嶋田裕亮,高秀雄,北弘志,磯部寛之
    • Organizer
      日本化学会第91春期年会1E5-28
    • Place of Presentation
      日本化学会第91春期年会(2011)講演予稿集
    • Year and Date
      2011-03-11
    • Related Report
      2011 Final Research Report
  • [Presentation] Disilanyl Double-Pillared Bisanthracenes : A New Molecular Design for Organic Electronic Materials2011

    • Author(s)
      Waka Nakanishi, Shunpei Hitosugi, Yusuke Shimada, Hideo Taka, Hiroshi Kita, Hiroyuki Isobe
    • Organizer
      46th EUCHEM Conference on Stereochemistry
    • Place of Presentation
      Brunnen, Swizerland
    • Related Report
      2011 Annual Research Report
  • [Presentation] 生体内分子を模倣するπ電子豊富分子の設計・合成2011

    • Author(s)
      中西和嘉・吉岡知昭・高秀雄・薛〓・北弘志・磯部寛之
    • Organizer
      高次π空間の創発と機能開発第6回公開シンポジウム
    • Place of Presentation
      岡崎コンファレンスセンター
    • Related Report
      2011 Annual Research Report
  • [Presentation] Nanocarbon-inspired Molecular Design : Interesting Stairs for Interdisciplinary Research2011

    • Author(s)
      Hiroyuki, Isobe
    • Organizer
      14th International Symposium on Novel Aromatic Compounds (ISNA-14)
    • Place of Presentation
      Eugine, Oregon USA(招待講演)
    • Related Report
      2011 Annual Research Report
  • [Presentation] Covalent "Double Helix" : Unexpected Emergence of Illusory Molecular Expression of Penrose Stairs2011

    • Author(s)
      Waka Nakanishi, Taisuke Matsuno, Junji Ichikawa, Hiroyuki Isobe
    • Organizer
      高次π空間の機能と開発第3回国際シンポジウム
    • Place of Presentation
      つくば国際会議場
    • Related Report
      2011 Annual Research Report
  • [Presentation] Design and Synthesis of Minimal Nanocarbons2011

    • Author(s)
      磯部寛之
    • Organizer
      The 6th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Shatin, Hong Kong(招待講演)
    • Related Report
      2011 Annual Research Report
  • [Presentation] [4]ヘリセン環状二量体の合成と構造2010

    • Author(s)
      松野太輔,中西和嘉,磯部寛之
    • Organizer
      平成22年度化学系学協会東北大会1P057
    • Place of Presentation
      盛岡
    • Year and Date
      2010-09-26
    • Related Report
      2011 Final Research Report
  • [Presentation] ジシラニル二重架橋ビスアントラセン:OLEDにおける両極性キャリア輸送材料2010

    • Author(s)
      一杉俊平,中西和嘉,アンナピスカリョーバ,嶋田裕亮,高秀雄,北弘志,磯部寛之
    • Organizer
      第21回基礎有機化学討論会A31
    • Place of Presentation
      名古屋
    • Year and Date
      2010-09-11
    • Related Report
      2011 Final Research Report
  • [Presentation] [4]ヘリセン環状二量体の合成と構造2010

    • Author(s)
      松野太輔,中西和嘉,磯部寛之
    • Organizer
      高次π空間の創発と機能開発第2回若手研究会
    • Place of Presentation
      筑波
    • Year and Date
      2010-07-15
    • Related Report
      2011 Final Research Report
  • [Presentation] πスタック型結晶構造をもつクリセン誘導体の合成法の開発2010

    • Author(s)
      一杉俊平,松野太輔,岩本武明,市川淳士,磯部寛之
    • Organizer
      日本化学会第90春期年会4G1-05
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] Functional Assembly of Amphiphilic Carbon Clusters2010

    • Author(s)
      Isobe, Hiroyuki
    • Organizer
      9th International Symposium on Functional π-Electron Systems
    • Place of Presentation
      Georgia, USA(招待講演)
    • Related Report
      2010 Annual Research Report
  • [Presentation] πスタック型結晶構造をもつクリセン誘導体の合成法の開発2009

    • Author(s)
      一杉俊平,松野太輔,岩本武明,市川淳士,磯部寛之
    • Organizer
      平成21年度化学系学協会東北大会3P044
    • Place of Presentation
      福島
    • Year and Date
      2009-09-21
    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.orgchem2.chem.tohoku.ac.jp/

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.orgchem2.chem.tohoku.ac.jp/

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.orgchem2.chem.tohoku.ac.jp/

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.orgchem2.chem.tohoku.ac.jp/

    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 有機エレクトロニクス素子用材料,有機エレクトロニクス素子,照明装置,表示装置及び有機薄膜太陽電池素子2011

    • Inventor(s)
      高秀雄,北弘志,磯部寛之,一杉俊平,中西和嘉
    • Industrial Property Rights Holder
      コニカミノルタホールディングス株式会社
    • Filing Date
      2011-03-24
    • Related Report
      2011 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
    • Filing Date
      2010-12-10
    • Related Report
      2011 Final 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

URL: 

Published: 2009-04-01   Modified: 2016-04-21  

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