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2013 Fiscal Year Final Research Report

Synthesis of chiral nanocalipers and nanotweezers and their application to separation of nanotubes and graphene

Research Project

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Project/Area Number 23350062
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionShiga University of Medical Science

Principal Investigator

KOMATSU Naoki  滋賀医科大学, 医学部, 准教授 (30253008)

Co-Investigator(Kenkyū-buntansha) UNO Hidemitu  愛媛大学, 理工学研究科, 教授 (20168735)
Co-Investigator(Renkei-kenkyūsha) MORI Shigeki  愛媛大学, 総合科学研究支援センター, 助教 (30572028)
Project Period (FY) 2011-04-01 – 2014-03-31
Keywordsフラーレン・ナノチューブ / 分子認識 / 分離
Research Abstract

We have been developing the methodology to discriminate the handedness and diameter of single-walled carbon nanotubes (SWNTs) through molecular recognition using chiral diporphyrin nanotweezers. Although relatively small diameters of SWNTs (less than 1.0 nm) were recognized well, nanotweezers were not able to form stable complexes with the SWNTs with the diameters larger than 1.0 nm. In this context, we designed chiral diporphyrin with much larger cavity; namely "nanocalipers". As expected, we obtained optically active SWNTs with more than 1.0 nm in diameter and, unexpectedly, enriched metallic SWNTs over semiconducting ones. The optically active metallic SWNTs are identified for the first time, in addition to the optically active semiconducting SWNTs with such large diameters. Higher selectivity to metallic SWNTs are observed in the case of pyrene-based nanocalipers.

  • Research Products

    (61 results)

All 2014 2013 2012 2011 Other

All Journal Article (19 results) (of which Peer Reviewed: 15 results) Presentation (29 results) (of which Invited: 17 results) Book (2 results) Remarks (1 results) Patent(Industrial Property Rights) (10 results)

  • [Journal Article] Bis(tert-butylpyrene) Nanotweezers and Nanocalipers : Enhanced Extraction and Recognition Abilities for Single-Walled Carbon Nanotubes2013

    • Author(s)
      G. Liu, A. F. M. M. Rahman, S. Chaunchaiyakul, T. Kimura, Y. Kuwahara, N. Komatsu
    • Journal Title

      Chem. Eur. J.

      Volume: 19 (48) Pages: 16221-16230

    • DOI

      10.1002/chem.201302799

    • Peer Reviewed
  • [Journal Article] Simultaneous Discrimination of Diameter, Handedness, and Metallicity of Single-Walled Carbon Nanotubes with Chiral Diporphyrin Nanocalipers2013

    • Author(s)
      G. Liu, F. Wang, S. Chunchaiyakul, Y. Saito, A. K. Bauri, T. Kimura, Y. Kuwahara, N. Komatsu
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 (12) Pages: 4805-4814

    • Peer Reviewed
  • [Journal Article] Enrichment of Large-Diameter Single-Walled Carbon Nanotubes (SWNTs) with Metallo-Octaethylporphyrins2013

    • Author(s)
      Y. Li, A. F. M. M. Rahman, G. Liu, Z. Xiong, K. Koezuka, Z. Xu, N. Komatsu, F. Wang
    • Journal Title

      Materials

      Volume: 6 (8) Pages: 3064-3078

    • Peer Reviewed
  • [Journal Article] A rosette cooling cell : more effective container for solubilization of single-walled carbon nanotubes under probe-type ultrasonic irradiation2013

    • Author(s)
      T. Yasumitsu, G. Liu, J.-M. Leveque, S. Aonuma, L. Duclaux, T. Kimura, N. Komatsu
    • Journal Title

      Ultrason. Sonochem

      Volume: 20 (1) Pages: 37-39

    • Peer Reviewed
  • [Journal Article] ロゼッタ型冷却容器を用いた単層カーボンナノチューブの分散2013

    • Author(s)
      小松直樹
    • Journal Title

      ケミカルエンジニアリング

      Volume: 58 (4) Pages: 66-69

  • [Journal Article] ナノ炭素材料化学における超音波2013

    • Author(s)
      小松直樹
    • Journal Title

      超音波テクノ

      Volume: 25 (1) Pages: 10-14

  • [Journal Article] Hyperbranched Polyglycerol-Grafted Superparamagnetic Iron Oxide Nanoparticles : Synthesis, Characterization, Functionalization, Size Separation, Magnetic Properties, and Biological Applications2012

    • Author(s)
      L. Zhao, T. Chano, S. Morikawa, Y. Saito, A. Shiino, S. Shimizu, T. Maeda, T. Irie, S. Aonuma, H. Okabe, T. Kimura, T.Inubushi, N. Komatsu
    • Journal Title

      Adv. Funct. Mater

      Volume: 22 (24) Pages: 5107-5117

    • Peer Reviewed
  • [Journal Article] Water redissoluble chiral porphyrin-carbon nanotube composites2012

    • Author(s)
      X. Peng, H. Qin, L. Li, Y. Huang, J. Peng, Y. Cao, N. Komatsu
    • Journal Title

      J. Mater. Chem.

      Volume: 22 (12) Pages: 5764-5769

    • Peer Reviewed
  • [Journal Article] Preferential extraction of left- or right-handed single-walled carbon nanotubes by use of chiral diporphyrin nanotweezers2012

    • Author(s)
      G. Liu, T. Yasumitsu, L. Zhao, X. Peng, F. Wang, A. K. Bauri, S. Aonuma, T. Kimura, N. Komatsu
    • Journal Title

      Org. Biomol. Chem.

      Volume: 10 (30) Pages: 5830-5836

    • Peer Reviewed
  • [Journal Article] Chromatographic Separation of Highly Soluble Diamond Nanoparticles Prepared by Polyglycerol Grafting2011

    • Author(s)
      L. Zhao, T. Takimoto, M. Ito, N. Kitagawa, T. Kimura, *N. Komatsu
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 50 (6) Pages: 1388-1392

    • Peer Reviewed
  • [Journal Article] Diameter-based separation of single-walled carbon nanotubes through selective extraction with dipyrene nanotweezers2011

    • Author(s)
      A. F. M. M. Rahman, F. Wang, K. Matsuda, T. Kimura, N. Komatsu
    • Journal Title

      Chem. Sci

      Volume: 2 (5) Pages: 862-867

    • Peer Reviewed
  • [Journal Article] Improved selectivity in discriminating handedness and diameter of single-walled carbon nanotubes with N-substituted 3,6-carbazolylene-bridged chiral diporphyrin nanotweezers2011

    • Author(s)
      F. Wang, K. Matsuda, A. F. M. M. Rahman, T. Kimura, N. Komatsu
    • Journal Title

      Nanoscale

      Volume: 3 (10) Pages: 4117-4124

    • Peer Reviewed
  • [Journal Article] Solid State NMR study of nanodiamond surface chemistry2011

    • Author(s)
      M. Dubois, K. Guerin, N. Batisse, E. Petit, A. Hamwi, N. Komatsu, H. Kharbache, P. Pirotte, F. Masin
    • Journal Title

      Solid State Nuclear Magnetic Resonance

      Volume: 40 (4) Pages: 144-154

    • Peer Reviewed
  • [Journal Article] Polyglycerol functionalization of ZnO nanoparticles for stable hydrosol in physiological media2011

    • Author(s)
      L. Zhao, T. Takimoto, T. Kimura, N. Komatsu
    • Journal Title

      J. Indian Chem. Soc.

      Volume: 88 Pages: 1787-1790

    • Peer Reviewed
  • [Journal Article] Secondary sonochemical effect on Mo-catalyzed bromination of aromatic compounds2011

    • Author(s)
      J.-M. Leveque, M. Fujita, A. Bosson, H. Sohmiya, C. Petrier, N. Komatsu, T. Kimura
    • Journal Title

      Ultrason. Sonochem.

      Volume: 18 (3) Pages: 753-756

    • Peer Reviewed
  • [Journal Article] Photophysical insights into supramolecular interaction of a designed bisporphyrin with fullerenes C60 and C702011

    • Author(s)
      D. Pal. M. Furukawa, N. Komatsu, H. Uno, S. Bhattacharya
    • Journal Title

      Spectrochimica Acta A

      Volume: 78 (1 ) Pages: 185-190

    • Peer Reviewed
  • [Journal Article] バイオテクノロジーにおける炭素材料の未来2011

    • Author(s)
      小松直樹
    • Journal Title

      New Diamond

      Volume: 100号記念号 Pages: 68-70

  • [Journal Article] Design, synthesis, and preliminary ex vivo and in vivo evaluation of cationic magnetic resonance contrast agent for rabbit articular cartilage imaging

    • Author(s)
      T. Irie, K. Oda, A. Shiino, M. Kubo, S. Morikawa, N. Urushiyama, S. Aonuma, T. Kimura, T. Inubushi, T. Oohashi, N. Komatsu
    • Journal Title

      Med. Chem. Commun

      Volume: (in press)

    • DOI

      10.1039/C3MD00229B

    • Peer Reviewed
  • [Journal Article] ナノダイヤモンドの臨床応用を目指して

    • Author(s)
      小松直樹
    • Journal Title

      New Diamond

      Volume: 112(印刷中)

  • [Presentation] Diporphyrin and Dipyrene Nanocalipers for Discrimination of Diameter and Metallicity in Single-Walled Carbon Nanotubes2014

    • Author(s)
      小松直樹, 劉剛
    • Organizer
      225th ECS meeting
    • Place of Presentation
      Orlando, US
    • Year and Date
      2014-05-13
    • Invited
  • [Presentation] Functionalization of Nanodiamond for Biomedical Applications2013

    • Author(s)
      小松直樹, Li Zhao
    • Organizer
      JSAP-MRS Joint Symposia
    • Place of Presentation
      Kyotanabe, Japan
    • Year and Date
      2013-09-16
    • Invited
  • [Presentation] Functionalization of Nanodiamond for Biomedical Applications2013

    • Author(s)
      小松直樹
    • Organizer
      EMN east meeting
    • Place of Presentation
      Beijing, China
    • Year and Date
      2013-09-09
    • Invited
  • [Presentation] ナノ炭素材料の水溶化, サイズ分離と生物医療応用2013

    • Author(s)
      小松直樹
    • Organizer
      第45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
    • Place of Presentation
      大阪大学, 大阪
    • Year and Date
      2013-08-07
    • Invited
  • [Presentation] Separation of Left- and Right-Handed Carbon Nanotubes2013

    • Author(s)
      小松直樹
    • Organizer
      Symmetry Festival 2013
    • Place of Presentation
      Delft, Netherlands
    • Year and Date
      2013-08-02
    • Invited
  • [Presentation] Chiral Diporphyrin Nanocalipers : New Host Molecule Next to Nanotweezers for Separation of Single-Walled Carbon Nanotubes2013

    • Author(s)
      小松直樹, 劉剛
    • Organizer
      223rd ECS meeting
    • Place of Presentation
      Toronto, Canada
    • Year and Date
      2013-05-13
    • Invited
  • [Presentation] Simultaneous Discrimination of Diameter, Handedness, and Metallicity of Single-Walled Carbon Nanotubes by Chiral Diporphyrin Nanocalipers2013

    • Author(s)
      小松直樹, 劉剛
    • Organizer
      223rd ECS meeting
    • Place of Presentation
      Toronto, Canada
    • Year and Date
      2013-05-13
    • Invited
  • [Presentation] 医療応用を目指したダイヤモンドナノ粒子の表面化学修飾2013

    • Author(s)
      小松直樹
    • Organizer
      旭ダイヤモンド工業(株)技術研究所
    • Place of Presentation
      千葉
    • Year and Date
      2013-03-14
    • Invited
  • [Presentation] ナノダイヤモンドのドラッグキャリア, イメージングプローブへの応用2012

    • Author(s)
      小松直樹
    • Organizer
      日油, 武豊工場
    • Place of Presentation
      愛知
    • Year and Date
      2012-12-12
    • Invited
  • [Presentation] Optical Resolution of Carbon Nanotubes through Molecular Recognition2012

    • Author(s)
      小松直樹
    • Organizer
      Bangladesh Chemical Congress 2012
    • Place of Presentation
      Dhaka, Bangladesh
    • Year and Date
      2012-12-08
    • Invited
  • [Presentation] Nanodiamond-based fluorescent probe for in vivo imaging : Derivatization and Characterization2012

    • Author(s)
      Naoki Komatsu, Li Zhao, Tokuhiro Chano
    • Organizer
      E-MRS Fall Meeting
    • Place of Presentation
      Warsaw, Poland
    • Year and Date
      2012-09-19
    • Invited
  • [Presentation] Precise and Facile Characterization of the Surface Functionalities of Diamond Nanoparticles in Their Organic Transformations2012

    • Author(s)
      Naoki Komatsu, Li Zhao, Tatsuya Takimoto
    • Organizer
      E-MRS Fall Meeting
    • Place of Presentation
      Warsaw, Poland
    • Year and Date
      2012-09-18
  • [Presentation] Hyperbranched Polyglycerol-Grafted Superparamagnetic Iron Oxide Nanoparticle for Biological Application2012

    • Author(s)
      Naoki Komatsu, Li Zhao, Tokuhiro Chano
    • Organizer
      E-MRS Fall Meeting
    • Place of Presentation
      Warsaw, Poland
    • Year and Date
      2012-09-18
  • [Presentation] Optical Resolution of Single-Walled Carbon Nanotubes through Molecular Recognition with Chiral Diporphyrin Nanotweezers2012

    • Author(s)
      Naoki Komatsu, Gang Liu
    • Organizer
      E-MRS Fall Meeting
    • Place of Presentation
      Warsaw, Poland
    • Year and Date
      2012-09-18
  • [Presentation] Nanodiamond-based fluorescent probe for in vivo imaging2012

    • Author(s)
      Naoki Komatsu, Li Zhao, Tokuhiro Chano
    • Organizer
      E-MRS Fall Meeting
    • Place of Presentation
      Warsaw, Poland
    • Year and Date
      2012-09-17
  • [Presentation] 拡張性, 柔軟性, 汎用性を兼ね備えた生体用イメージングプローブの開発2012

    • Author(s)
      小松直樹
    • Organizer
      大阪大学タンパク研究所セミナー
    • Place of Presentation
      大阪大学タンパク研究所, 大阪
    • Year and Date
      2012-08-01
    • Invited
  • [Presentation] Separation of Left- and Right-Handed Structures of Single-Walled Carbon Nanotubes through Molecular Recognition2012

    • Author(s)
      Naoki Komatsu, Xiaobin Peng, Feng Wang, Ajoy Bauri, A. F. M. Mustafizur Rahman, and Gang Liu
    • Organizer
      International Symposium on Carbon Nanotube Nanoelectronics (CNTNE)
    • Place of Presentation
      Nagoya, Japan
    • Year and Date
      2012-06-12
  • [Presentation] Chromatographic Separation of Highly Soluble Nanodiamond Prepared by Polyglycerol Grafting2012

    • Author(s)
      Naoki Komatsu, and Takimoto Tatsuya
    • Organizer
      221st ECS meeting
    • Place of Presentation
      Seattle, USA
    • Year and Date
      2012-05-10
  • [Presentation] Diporphyrin Nanotweezers for Discrimination of the Diameter and Handedness of Single-Walled Carbon Nanotubes2012

    • Author(s)
      小松直樹
    • Organizer
      221st ECS meeting
    • Place of Presentation
      Seattle, USA
    • Year and Date
      2012-05-09
    • Invited
  • [Presentation] Optically Active Single-Walled Carbon Nanotubes2012

    • Author(s)
      小松直樹
    • Organizer
      221st ECS meeting
    • Place of Presentation
      Seattle, USA
    • Year and Date
      2012-05-08
    • Invited
  • [Presentation] Sonochemistry for carbon nanotubes2011

    • Author(s)
      小松直樹, 木村隆英
    • Organizer
      The International Workshop on Advanced Sonochemistry 2011
    • Place of Presentation
      名古屋大学
    • Year and Date
      2011-11-04
    • Invited
  • [Presentation] Optical Resolution of Carbon Nanotubes through Molecular Recognition2011

    • Author(s)
      Naoki Komatsu
    • Organizer
      World Congress of Catalytic Asymmetric Synthesis 2011
    • Place of Presentation
      Beijing, China
    • Year and Date
      2011-08-10
  • [Presentation] Preparation of Fluorescent Nanodiamond Stably Dispersed under a Physiological Environment and Its Application to Cellular Imaging2011

    • Author(s)
      Naoki Komatsu, Tatsuya Takimoto, Li Zhao, Naoko Kitagawa, Takahide Kimura
    • Organizer
      Carbon 2011
    • Place of Presentation
      Shanhai, China
    • Year and Date
      2011-07-27
  • [Presentation] Chromatographic Separation of Highly Soluble Nanodiamond Prepared by Polyglycerol Grafting2011

    • Author(s)
      Naoki Komatsu, Li Zhao, Tatsuya Takimoto, Masaaki Ito, Naoko Kitagawa, Takahide Kimura
    • Organizer
      Carbon 2011
    • Place of Presentation
      Shanhai, China
    • Year and Date
      2011-07-25
  • [Presentation] Optical Resolution of Single-Walled Carbon Nanotubes through Molecular Recognition with Chiral Diporphyrin Nanotweezers2011

    • Author(s)
      Naoki Komatsu, Feng Wang, Xiaobin Peng, Takahide Kimura
    • Organizer
      Carbon 2011
    • Place of Presentation
      Shanhai, China
    • Year and Date
      2011-07-25
  • [Presentation] Chromatographic Separation of Highly Soluble Nanodiamond Prepared by Polyglycerol Grafting2011

    • Author(s)
      L. Zhao, T. Takimoto, M. Ito, N. Kitagawa, T. Kimura, N. Komatsu
    • Organizer
      NDNC2011
    • Place of Presentation
      Matsue, Japan
    • Year and Date
      2011-05-18
  • [Presentation] Preparation of Fluorescent Diamond Nanoparticles Stably Dispersed under Physiological Environment through Multi-Step Organic Transformations2011

    • Author(s)
      Naoki Komatsu, and Takimoto Tatsuya
    • Organizer
      219th ECS meeting
    • Place of Presentation
      Montreal, Canada
    • Year and Date
      2011-05-04
  • [Presentation] Diameter-Based Separation of Single-Walled Carbon Nanotubes with Dipyrene Nanotweezers2011

    • Author(s)
      小松直樹
    • Organizer
      219th ECS meeting
    • Place of Presentation
      Montreal, Canada
    • Year and Date
      2011-05-02
    • Invited
  • [Presentation] フラーレン, カーボンナノチューブ, グラフェン, ナノダイヤモンドを分ける2011

    • Author(s)
      小松直樹
    • Organizer
      特定領域研究合同研究会"炭素系物質科学の現状と今後"
    • Place of Presentation
      東京理科大学, 東京
    • Year and Date
      2011-01-27
    • Invited
  • [Book] "Synthesis, Size Separation, Characterization and Surface Engineering of Superparamagnetic Iron Oxide Nanoparticles for Biomedical Applications" Magnetic Nanoparticles : Synthesis, Physicochemical Properties and Role in Biomedicine; N. P. Sabbas, Ed.2014

    • Author(s)
      L. Zhao, and N. Komatsu
    • Total Pages
      95-111
    • Publisher
      Nova Science Publishers, Inc.: New York
  • [Book] Separation of Left- and Right-Handed Structures of Single-Walled Carbon Nanotubes through Molecular Recognition" Handbook of Biomedical Applications of Carbon Nanomaterials; K. M. Kadish and F. D'souza, Eds.2012

    • Author(s)
      G. Liu, F. Wang, X. Peng, A. F. M. M. Rahman, A. K. Bauri, *N. Komatsu
    • Total Pages
      203-232
    • Publisher
      World Scientific
  • [Remarks]

    • URL

      http://www.shiga-med.ac.jp/~nkomatsu/indexj.htm

  • [Patent(Industrial Property Rights)] 抗癌剤が担持されたナノ粒子2014

    • Inventor(s)
      小松直樹, 趙利
    • Industrial Property Rights Holder
      滋賀医科大学
    • Industrial Property Number
      特願2014-019704
    • Filing Date
      2014-02-04
  • [Patent(Industrial Property Rights)] 表面修飾ナノダイヤモンド及びその製造法2013

    • Inventor(s)
      小松直樹, 伊藤雅章
    • Industrial Property Rights Holder
      ダイセル化学工業(株)
    • Industrial Property Number
      特許5275088
    • Filing Date
      2013-05-24
  • [Patent(Industrial Property Rights)] Surface Modified Nanodiamond and Its Producing Method2013

    • Inventor(s)
      Naoki Komatsu, Masaaki Ito
    • Industrial Property Number
      USP 8410196
    • Filing Date
      2013-04-02
  • [Patent(Industrial Property Rights)] ナノダイヤモンド2012

    • Inventor(s)
      小松直樹, 門田直樹, 木村隆英
    • Industrial Property Rights Holder
      小松直樹, トーメイダイヤ(株)
    • Industrial Property Number
      特許5346427
    • Filing Date
      2012-05-25
  • [Patent(Industrial Property Rights)] カーボンナノチューブの環状集合体の製造方法および製造装置2012

    • Inventor(s)
      小松直樹, 木村隆英
    • Industrial Property Rights Holder
      京都大学他
    • Industrial Property Number
      特許5001544
    • Filing Date
      2012-05-25
  • [Patent(Industrial Property Rights)] ダイヤモンド微細粉の捕集方法2012

    • Inventor(s)
      小松直樹, 森田陽一他
    • Industrial Property Rights Holder
      石塚博, 小松直樹
    • Industrial Property Number
      特許5276995
    • Filing Date
      2012-05-24
  • [Patent(Industrial Property Rights)] Minute Diamond Powder, Method for Collecting the Same and Slurry Comprising the Same in Suspension2011

    • Inventor(s)
      Youichi Morita, Tatsuya Takimoto, Naoki Komatsu, Hiroshi Yamanaka, Hisao Shirasawa, Hiroshi Ishizuka
    • Industrial Property Number
      US 2011/0052915
    • Filing Date
      2011-03-03
  • [Patent(Industrial Property Rights)] 蛍光ナノダイヤモンド2011

    • Inventor(s)
      小松直樹, 長町信治
    • Industrial Property Rights Holder
      滋賀医科大学
    • Industrial Property Number
      特願2011-071312(特開2012-206863)
    • Filing Date
      2011-03-29
  • [Patent(Industrial Property Rights)] MR画像法に利用する生体標識用ナノダイヤモンド2011

    • Inventor(s)
      犬伏俊郎, 小松直樹, 森田将史, 長町信治, 佐々木玄
    • Industrial Property Rights Holder
      (株)イオンテクノセンター
    • Industrial Property Number
      特許4874751
    • Filing Date
      2011-12-02
  • [Patent(Industrial Property Rights)] カーボンナノチューブの精製方法2011

    • Inventor(s)
      小松直樹, 大須賀篤弘, 磯田正二, 中嶋直敏, 村上裕人
    • Industrial Property Rights Holder
      京都大学他
    • Industrial Property Number
      特許4868490
    • Filing Date
      2011-11-25

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Published: 2015-06-25  

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