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Synthesis of highly strained cycloparaphenylenes and elucidation of their properties

Research Project

Project/Area Number 26410043
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

Kayahara Eiichi  京都大学, 化学研究所, 助教 (10610553)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsシクロパラフェニレン / フラーレン / カーボンナノチューブ / 曲面状π共役分子 / スズ / 還元的芳香族化 / 電気化学測定 / 電子物性 / 環状π共役分子 / 歪み / 大量合成 / 芳香族化 / 臭素化 / 官能基化 / バンドギャップ / 電子状態 / 電気化学的測定
Outline of Final Research Achievements

Curved π-conjugated molecules have been the focus of intensive research because of their aesthetic structure and associated distinct properties, as well as potential application in materials science. Cycloparaphenylenes (CPPs), in particular, have emerged a prominent position in this field because of their availability by bottom-up organic synthesis. Despite of their synthetic development, however, synthesis of highly strained [5]CPP, a structural unit of the periphery of C60 and a shortest possible structural constitute of the sidewall of (5,5) carbon nanotube, has not been reported at the beginning of this research. In this research, [5]CPP was synthesized for the first time. The UV-vis and electrochemical studies revealed that the HOMO-LUMO gap of [5]CPP is narrow and is comparable to that of C60 as predicted by the theoretical calculation. The results suggest that [5]CPP should be an excellent lead compound for molecular electronics.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (53 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (2 results) Journal Article (17 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 16 results,  Acknowledgement Compliant: 14 results,  Open Access: 2 results) Presentation (31 results) (of which Int'l Joint Research: 6 results,  Invited: 5 results) Book (1 results) Remarks (2 results)

  • [Int'l Joint Research] University of Oregon(米国)

    • Related Report
      2015 Research-status Report
  • [Int'l Joint Research] University of Geneva(スイス)

    • Related Report
      2015 Research-status Report
  • [Journal Article] Synthesis and physical properties of [4]cyclo-3,7-dibenzo[b,d]thiophene and its S,S-dioxide2017

    • Author(s)
      Kayahara, E.; Zhai, X.; Yamago, S.
    • Journal Title

      Can. J. Chem.

      Volume: 95 Issue: 4 Pages: 351-356

    • DOI

      10.1139/cjc-2016-0474

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Shortest Double-Walled Carbon Nanotubes Composed of Cycloparaphenylenes2017

    • Author(s)
      Hashimoto, S.; Iwamoto, T.; Kurachi, D.; Kayahara, E.; Yamago, S.
    • Journal Title

      ChemPlusChem

      Volume: 印刷中 Issue: 7 Pages: 1015-1020

    • DOI

      10.1002/cplu.201700097

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Tetracyclo(2,7-Carbazole)s: Aromaticity Probe for Cycloparaphenylenes2016

    • Author(s)
      Kuroda, Y.; Sakamoto, Y.; Suzuki, T.; Kayahara, E.; Yamago, S.
    • Journal Title

      J. Org. Chem.

      Volume: 81 Pages: 3356-3363

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Size Dependence of [N]Cycloparaphenylenes (N = 5-12) in Electrochemical Oxidation2016

    • Author(s)
      Eiichi Kayahara, Kei Fukayama, Tohru Nishinaga, and Shigeru Yamago
    • Journal Title

      Chem. Asian. J.

      Volume: 11 Issue: 12 Pages: 1793-1797

    • DOI

      10.1002/asia.201600582

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective Synthesis and Characterization of Multinuclear Convex-bounded Ruthenium-[n]Cycloparaphenylene (n = 5 and 6) Complexes2016

    • Author(s)
      Kayahara, E.; Patel, V. K.; Mercier, A.; Kündig, E. P.; Yamago, S.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 1 Pages: 302-306

    • DOI

      10.1002/anie.201508003

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Synthesis and Characterization of [n]CPP (n = 5, 6, 8, 10, and 12) Radical Cation and Dications: Size-Dependent Absorption, Spin, and Charge Delocalization2016

    • Author(s)
      Eiichi Kalahari, Takahiko Kouyama, Tatsuhisa Kato, Shigeru Yamago
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 1 Pages: 338-344

    • DOI

      10.1021/jacs.5b10855

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective and Gram-scale Synthesis of [6]Cycloparaphenylene2015

    • Author(s)
      Kayahara, E.; Patel, V. K.; Xia, J.; Jasti, R.; Yamago, S.
    • Journal Title

      Synlett

      Volume: 26 Issue: 11 Pages: 1615-1619

    • DOI

      10.1055/s-0034-1380714

    • NAID

      120005670844

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Radical Ions of Cyclopyrenylene: Comparison of Spectral Proeperties with Cycloparaphenylene2015

    • Author(s)
      Fujitsuka, M.; Tojo, S.; Iwamoto, T.; Kayahara, E.; Yamago, S.; Majima, T.
    • Journal Title

      J. Phys. Chem. A

      Volume: 115 Issue: 18 Pages: 4136-4141

    • DOI

      10.1021/acs.jpca.5b01189

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ligand-controlled Synthesis of [3]- and [4]Cyclo-9,9-dimethyl-2,7-fluorenes through Triangle- and Square-shaped Platinum Intermediates2015

    • Author(s)
      Kayahara, E; Qu, R.; Kojima, M.; Iwamoto, T.; Suzuki, T.; Yamago, S.
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 52 Pages: 18939-18943

    • DOI

      10.1002/chem.201504369

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] In-plane Aromaticity in Cycloparaphenylene Dications: A Magnetic Circular Dichroism and Theoretical Study2015

    • Author(s)
      N. Toriumi, A. Muranaka, E. Kayahara, S. Yamago, and M. Uchiyama
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 1 Pages: 82-85

    • DOI

      10.1021/ja511320f

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Practical Synthesis for [n]Cycloparaphenylenes (n = 5, 7-12) by H2SnCl4-Mediated Aromatization of 1,4-Dihydroxylcyclo-2,5-diene Precursors2015

    • Author(s)
      Patel, V. K.; Kayahara, E.; Yamago, S.
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 15 Pages: 5742-5749

    • DOI

      10.1002/chem.201406650

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Characterization of [5]Cycloparaphenylene2014

    • Author(s)
      Kayahara, E.; Patel, V. K.; Yamago, S.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 6 Pages: 2284-2287

    • DOI

      10.1021/ja413214q

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Characterization, and Properties of [4]Cyclo-2,7-pyrenylene: Effect of Cyclic Structure on the Electronic Properties of Pyrene Oligomers2014

    • Author(s)
      Iwamoto, T.; Kayahara, E.; Yasuda, N.; Suzuki, T.; Yamago, S.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Issue: 25 Pages: 6430-6434

    • DOI

      10.1002/anie.201403624

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Properties of triplet-excited [n]cycloparaphenylenes (n = 8-12): Excitation energies lower than those of linear oligomers and polymers2014

    • Author(s)
      Mamoru Fujitsuka, Chao Lu, Takahiro Iwamoto, Eiichi Kayahara, Shigeru Yamago, and Tetsuro Majima
    • Journal Title

      The Journal of Physical Chemistry A

      Volume: 118 Issue: 25 Pages: 4527-4532

    • DOI

      10.1021/jp504689q

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Radical ions of cycloparaphenylenes: Size dependence contrary to the neutral molecules2014

    • Author(s)
      Mamoru Fujitsuka, Sachiko Tojo, Takahiro Iwamoto, Eiichi Kayahara, Shigeru Yamago, and Tetsuro Majima
    • Journal Title

      The Journal of Physical Chemistry Letters

      Volume: 5 Issue: 13 Pages: 2302-2305

    • DOI

      10.1021/jz5009054

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] ついに完成!世界最小の炭素ナノリング -五つのベンゼン環をリング状につなげる合成法の開発-2014

    • Author(s)
      茅原栄一, 山子茂
    • Journal Title

      化学

      Volume: 69 Pages: 32-36

    • Related Report
      2014 Research-status Report
    • Open Access / Acknowledgement Compliant
  • [Journal Article] New Organic Chemistry of Three-Dimensional π-Conjugated Compounds2014

    • Author(s)
      山子茂, 茅原栄一, 岩本貴寛
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 72 Issue: 9 Pages: 992-1005

    • DOI

      10.5059/yukigoseikyokaishi.72.992

    • NAID

      130004699587

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthetic Study of [4]Cycloparaphenylene2017

    • Author(s)
      Kayahara, E.; Yamago, S.
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthetic Study of Cyclic Azulene Oligomers from Cyclic Platinum Complexes2017

    • Author(s)
      Li, W.; Kayahara, E.; Yamago, S.
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] シクロパラフェニレンと1,2,4-トリアゾリン-3,5-ジオンの[4+2]環化付加反応2017

    • Author(s)
      曲睿; 茅原栄一; 山子茂
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthetic Study of Tube-shaped Molecular from [10]Cycloparaphenylene Derivatives2017

    • Author(s)
      Sun, L.; Kaiase, M.; Kayahara, E.; Matsuo, Y.; Yamago, S.
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] 環状π共役分子化学の最近の展開2017

    • Author(s)
      茅原栄一
    • Organizer
      産研ナノテクセンター若手セミナー「産研・化研ナノテク若手合同セミナー」
    • Place of Presentation
      大阪市
    • Year and Date
      2017-03-06
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Cycloparaphenylene (CPP) Derivatives Using Metalated CPPs2016

    • Author(s)
      曲睿; 茅原栄一; 山子茂
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      東京都
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] 曲面構造を持つπ共役分子の構築と機能2016

    • Author(s)
      茅原栄一
    • Organizer
      平成28年度第一回有機金属研究者の会
    • Place of Presentation
      東京都
    • Year and Date
      2016-09-13
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] サイズの異なるシクロパラフェニレン間のホストーゲスト化学2016

    • Author(s)
      橋本士雄磨; 岩本貴寛; 倉知大介; 河野太郎; 茅原栄一; 山子茂
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島市
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] [6]シクロパラフェニレンのグラムスケール合成2016

    • Author(s)
      茅原栄一、Patel Vijay Kumar、山子茂
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] 環状白金錯体と還元的芳香族化を用いたシクロパラフェニレン誘導体の合成2016

    • Author(s)
      大西弘晃、孫連盛、茅原栄一、山子茂
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] シクロパラフェニレンの臭素付加反応2016

    • Author(s)
      曲睿、茅原栄一、山子茂
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of Cycloparaphenylene (CPP) Derivatives Based on Bromination of CPPs2016

    • Author(s)
      Qu, R.; Kayahara, E.; Yamago, S.
    • Organizer
      Institute for Chemical Research International Symposium 2016 (ICRIS'16)-Research Network Based on ICR MOU-
    • Place of Presentation
      Uji, Japan
    • Year and Date
      2016-03-07
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Host-guest Chemistry for Cycloparaphenylenes with Different Diameter2016

    • Author(s)
      Hashimoto, S.; Kurachi, D.; Iwamoto, T.; Kono, T.; Kayahara, E.; Yamago, S.
    • Organizer
      Institute for Chemical Research International Symposium 2016 (ICRIS'16)-Research Network Based on ICR MOU-
    • Place of Presentation
      Uji, Japan
    • Year and Date
      2016-03-07
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Physical Properties of Oxygenated Cycloparaphenylenes2015

    • Author(s)
      Onishi, H.; Kayahara, E.; Yamago, S.
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem) 2015
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-18
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Regioselective Synthesis and Characterization of Multinuclear Convex-Bounded Ruthenium-Cycloparapheneylene Complexes2015

    • Author(s)
      Kayahara, E.; Patel, V. K.; Mercier, A.; Kuendig, E. P.; Yamago, S.
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Reactivity of Cycloparaphenylenes in Electrophilic Bromination2015

    • Author(s)
      Qu, R.; Kayahara, E.; Yamago, S.
    • Organizer
      2nd Annual Symposiuim of the International Research Training Group 2027
    • Place of Presentation
      Munster, Germany
    • Year and Date
      2015-10-05
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Characterization of Mono- and Multinuclear Ruthenium-Cycloparaphenylene Complexes2015

    • Author(s)
      茅原栄一、Patel Vijay Kumar、Mercier Audrey、Kündig Peter E、山子茂
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Practical Synthesis for [n]Cycloparaphenylenes by H2SnCl4-Mediated Aromatization2015

    • Author(s)
      Patel Vijay Kumar、茅原栄一、山子茂
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学
    • Year and Date
      2015-09-08
    • Related Report
      2015 Research-status Report
  • [Presentation] 環状π共役系化合物の合成とその物性2015

    • Author(s)
      茅原栄一
    • Organizer
      CREST「プロセスインテグレーションに向けた高機能ナノ構造体の創出」第5回公開シンポジウム
    • Place of Presentation
      東京、品川
    • Year and Date
      2015-06-04
    • Related Report
      2015 Research-status Report
  • [Presentation] 放射光によるナノカーボン類の分子構造解析2015

    • Author(s)
      茅原栄一
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-29
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] A Practical Synthesis of [n]CPPs Using Tin-mediated Reductive Aromatization2015

    • Author(s)
      Patel Vijay Kumar、茅原栄一、山子茂
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] シクロパラフェニレンールテニウム錯体の合成と同定2015

    • Author(s)
      茅原栄一, Patel Vijay Kumar, Kundig Peter E, Mercier Audrey, 山子茂
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] [5]シクロパラフェニレンの直接官能基化2015

    • Author(s)
      茅原栄一、Patel Vijay Kumar、山子茂
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 白金多核錯体を用いたペルフルオロシクロパラフェニレンの合成2015

    • Author(s)
      河野太郎、橋本士雄磨、茅原栄一、黒田康弘、鈴木敏泰、山子茂,
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 白金多核錯体を用いた環状共役ポルフィリンオリゴマーの合成2015

    • Author(s)
      前田祐希、茅原栄一、山子茂
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 酸素官能基を持つシクロパラフェニレンの酸化還元挙動2015

    • Author(s)
      大西弘晃、茅原栄一、山子茂
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] テトラシクロ(2,7-カルバゾール):芳香環内部における環電流2015

    • Author(s)
      黒田康弘、阪本洋一、鈴木敏泰、茅原栄一、山子茂
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis and physical properties of a ball-like three-dimensional π-conjugated molecule2014

    • Author(s)
      茅原栄一
    • Organizer
      化学研究所第114回研究発表会
    • Place of Presentation
      京都大学宇治キャンパス
    • Year and Date
      2014-12-12
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Synthesis and Properties of Curved -conjugated molecules2014

    • Author(s)
      Eiichi Kayahara
    • Organizer
      3rd International Conference and Exhibition on Materials Science & Engineering
    • Place of Presentation
      San Antonio, USA
    • Year and Date
      2014-10-08
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Synthesis of [5]Cycloparaphenylene2014

    • Author(s)
      茅原栄一、Patel Vijay Kumar、山子茂
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学
    • Year and Date
      2014-09-23
    • Related Report
      2014 Research-status Report
  • [Presentation] シクロパラフェニレンの酸化特性の解明2014

    • Author(s)
      茅原栄一、深山慧、香山貴彦、加藤立久、西長亨、山子茂
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学
    • Year and Date
      2014-09-09
    • Related Report
      2014 Research-status Report
  • [Book] Polycyclic Arenes and Heteroarenes: Synthesis, Properties, and Applications, Qian, M. Ed., John Wiley & Sons Ltd, Chichester, UK2015

    • Author(s)
      Yamago, S.; Kayahara, E.; Hashimoto, S.
    • Total Pages
      20
    • Publisher
      John Wiley & Sons Ltd
    • Related Report
      2015 Research-status Report
  • [Remarks] 世界最小の“炭素ナノリング”の化学合成に成功

    • URL

      http://www.kuicr.kyoto-u.ac.jp/a_topics/topics_140127.html

    • Related Report
      2014 Research-status Report
  • [Remarks] 世界最小の「ナノ炭素リング」の化学合成に成功

    • URL

      http://www.kyoto-u.ac.jp/static/ja/news_data/h/h1/news6/2013_1/140129_1.htm

    • Related Report
      2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2022-02-16  

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