Development of the chemical functionalization of carbon nanotubes and control of its property

• Project/Area Number: 23750035
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Tokyo Gakugei University
• Principal Investigator: MAEDA Yutaka 東京学芸大学, 教育学部, 准教授 (10345324)
• Project Period (FY): 2011 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2011: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
• Keywords: カーボンナノチューブ / 化学修飾 / 分子変換 / フラーレン / 機能化 / ケイ素化 / 有機ケイ素化合物

Research Abstract

In this project, development of the chemical functionalization of carbon nanotubes and control of its property were studied. Reductive alkylation of single-walled carbon nanotubes (SWNTs) was conducted and its results showed significant substituent effects on the degree of functionalization of SWNTs. Addition of reactive substituent was successfully achieved using protectional group. Preparation and analysis of di-alkylated SWNTs having various substituents through two-step reductive alkylation were conducted. The degree of the functionalization on SWNTs (Bu-SWNTs-Bu) were determined by the absorption and Raman spectroscopy and the thermogravimetric analysis (TGA) and there is a good relation between Raman spectra and TGA. On the basis of the relation between Raman spectra and TGA, the ratio of 2R to 1R of 1R-SWNTs-2R (formula mass: 1R ≠ 2R) was determined. We also developed the chiral-selective photoreaction of SWNTs with organosulfur compounds in the presence of oxygen.

Research Products

• [Journal Article] Helicity Selective Photoreaction of Single-walled Carbon Nanotubes with Organosulfur Compounds in the Presence of OxygenY. (2013)
  • Author(s): Y. Maeda, J. Higo, Y. Amagai, J. Matsui, K. Ohkubo, Y. Yoshigoe, M. Hashimoto, K. Eguchi, M. Yamada, T. Hasegawa, Y. Sato, J. Zhou, J. Lu, T. Miyashita, S. Fukuzumi, T. Murakami, K. Tohji, S. Nagase, T. AkasakaJ
  • Journal Title: Am. Chem. Soc Volume: 135 Pages: 6356-6362
  • Peer Reviewed
• [Journal Article] Mechanistic Study of the Diels-Alder Reaction of Paramagnetic Endohedral MetallofullereneReaction of La@C82 with1,2,3,4,5-PentamethylcyclopentadieneS (2013)
  • Author(s): Y. Maeda, J.-D. Guo, M. Yamada, N. Mizorogi, S. Nagase, T. Akasaka,J
  • Journal Title: Am. Chem. Soc Volume: 135 Pages: 5582-5587
  • Peer Reviewed
• [Journal Article] Helicity Selective Photoreaction of Single-walled Carbon Nanotubes with Organosulfur Compounds in the Presence of Oxygen (2013)
  • Author(s): Maeda, Y.; Higo, J.; Amagai, Y.; Matsui, J.; Ohkubo, K.; Yoshigoe, Y.; Hashimoto, M.; Eguchi, K.; Yamada, M.; Hasegawa, T.; Sato, Y.; Zhou, J.; Lu, J.; Miyashita, T.; Fukuzumi, S.; Murakami, T.; Tohji, K.; Nagase, S; Akasaka, T.
  • Journal Title: J. Am. Chem. Soc. Volume: 135 Issue: 16 Pages: 6356-6362
  • DOI: 10.1021/ja402199n
  • Peer Reviewed
• [Journal Article] Mechanistic Study of the Diels-Alder Reaction of Paramagnetic Endohedral Metallofullerene: Reaction of La@C82 with 1,2,3,4,5-Pentamethylcyclopentadiene (2013)
  • Author(s): Sato, S.; Maeda, Y.; Guo, J. -D.; Yamada, M.; Mizorogi, N.; Nagase, S.; Akasaka, T.
  • Journal Title: J. Am. Chem. Soc. Volume: 135 Issue: 15 Pages: 5582-5587
  • DOI: 10.1021/ja309763f
  • Peer Reviewed
• [Journal Article] Analysis of Functionalization Degree of Single-Walled Carbon Nanotubes Having Various SubstituentsY (2012)
  • Author(s): Y. Maeda, K. Saito, N. Akamatsu, Y. Chiba, S.Ohno, Y. Okui, M.Yamada, T. Hasegawa, M. Kako, T. AkasakaJ.
  • Journal Title: Am. Chem. Soc Volume: 134 Pages: 18101-18108
  • Peer Reviewed
• [Journal Article] Interaction of Single-walled carbon Nanotubes with amine (2012)
  • Author(s): Y. Maeda, M. Yamada, T. Hasegawa, T. Akasaka, J. Lu, S. NagaseNANO
  • Journal Title: Brief Reports and Reviews Volume: 7
  • Peer Reviewed
• [Journal Article] Analysis of Functionalization Degree of Single-Walled Carbon Nanotubes Having Various Substituents (2012)
  • Author(s): Y. Maeda, K.Saito, N. Akanlatsu, Y. Chiba, S. Ohno, Y. Okui, M. Yamada, T. Hasegawa, M. Kako, T. Akasaka
  • Journal Title: J. Am. Chem. Soc Volume: 134 Issue: 43 Pages: 18101-18108
  • DOI: 10.1021/ja308969p
  • Peer Reviewed
• [Journal Article] Interaction of Single-walled Carbon Nanotubes with Amine (2012)
  • Author(s): Maeda, Y., Yamada, M., Hasegawa, T., Akasaka. T., Lu, J., Nagase, S.
  • Journal Title: NANO: Brief Reports and Reviews Volume: 7 Issue: 01 Pages: 11300011-10
  • DOI: 10.1142/s1793292011300015
  • Peer Reviewed
• [Journal Article] Oxygen Atom Transfer from PeroxideIntermediates to Fullerenes (2011)
  • Author(s): Y. Maeda, Y. Niino, T. Kondo, M. Yamada, T. Hasegawa, T.
  • Journal Title: AkasakaChem. Lett Volume: 40 Pages: 1431-1433
  • Peer Reviewed
• [Journal Article] Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition (2011)
  • Author(s): M.Yamada, C.I.Someya, T.Nakahodo, Y.Maeda, T.Tsuchiya, T.Akasaka
  • Journal Title: Molecules Volume: 16 Issue: 11 Pages: 9495-9504
  • DOI: 10.3390/molecules16119495
  • Peer Reviewed
• [Journal Article] Oxygen atom transfer from peroxide intermediates to fullerenes (2011)
  • Author(s): Maeda, Y., Niino, Y., Kondo, T., Yamada, M., Hasegawa, T., Akasaka, T.
  • Journal Title: Chemistry Letters Volume: 40 Issue: 12 Pages: 1431-1433
  • DOI: 10.1246/cl.2011.1431
  • NAID: 10030221607
  • Peer Reviewed
• [Presentation] 異なる置換基を有する単層カーボンナノチューブの化学修飾率の評価 (2013)
  • Author(s): 前田 優
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学（滋賀県）
• [Presentation] 活性酸化種を用いたフラーレンの酸化反応 (2012)
  • Author(s): 前田優・山田道夫・長谷川正・赤阪健
  • Organizer: 第39回有機典型元素化学討論会
  • Place of Presentation: いわて県民情報交流センター(岩手)
  • Year and Date: 2012-12-06
• [Presentation] A Role of Heteroatom in Chemistry of Single-walled Carbon Nanotubes (2012)
  • Author(s): 前田優
  • Organizer: The 3rd Tsukuba International Mini-symposium on Hybridization between Main Group Element Chemistry andπ-Electron Chemistry-ICHAC-10Pre-symposium in Tsukuba-
  • Place of Presentation: 筑波大学(茨城県)
  • Year and Date: 2012-05-18
• [Presentation] 異なる置換基を有する単層カーボンナノチューブの化学修飾率の評価 (2012)
  • Author(s): 石本清視・齊藤和磨・山田道夫・前田優・長谷川正・赤阪健
  • Organizer: 第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス(滋賀)
• [Presentation] Selective Functionalization of Single-Walled Carbon Nanotubes (2012)
  • Author(s): Y. Maeda, Y. Amagai, J. Higo, J. Matsui, M. Yamada, T. Hasegawa, J. Lu, S. Nagase, T. Akasaka
  • 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
  • Place of Presentation: 東北大学(宮城県)
• [Presentation] A Role of Heteroatom in Chemistry of Single-walled Carbon Nanotubes (2012)
  • Author(s): Yutaka Maeda
  • Organizer: The 3rd Tsukuba International Mini-symposium on Hybridization between Main Group Element Chemistry and π-Electron Chemistry ― ICHAC-10 Pre-symposium in Tsukuba
  • Place of Presentation: 筑波大学（茨城県）
  • Invited
• [Presentation] Selective Functionalization of Single-Walled Carbon Nanotubes (2012)
  • Author(s): 前田 優
  • 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
  • Place of Presentation: 東北大学（宮城県）
• [Presentation] 活性酸化種を用いたフラーレンの酸化反応 (2012)
  • Author(s): 前田 優
  • Organizer: 第39回有機典型元素化学討論会
  • Place of Presentation: いわて県民情報交流センター（岩手県）
• [Presentation] 金属内包フラーレンとアジリジンの反応 (2011)
  • Author(s): 前田優、上田ちひろ、菊地徹、山田道夫、長谷川正、赤阪健
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 石川県立音楽堂邦楽ホール(石川県)
• [Presentation] カーボンナノチューブのハロゲン化アルキルによる還元的化学修飾 (2011)
  • Author(s): 斉藤和磨・千葉友莉子・赤松範久・山田道夫・前田優・長谷川正・赤阪健
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば国際会議場(茨城県)
• [Presentation] Dispersion, separation, and functionalization of single-walled carbon nanotubes (2011)
  • Author(s): 前田優
  • Organizer: 筑波大学戦略イニシアティブ(A) 機能物質創製研究拠点第1回国際シンポジウム
  • Place of Presentation: 筑波大学(茨城県)
• [Presentation] カーボンナノチューブ透明導電性膜における長さとヘリシティーの影響 (2011)
  • Author(s): 小森谷一記・浦野裕貴・山田道夫・前田優・長谷川正・赤阪健
  • Organizer: 第5回関東支部大会
  • Place of Presentation: 東京農工大学(茨城県)
• [Presentation] カーボンナノチューブ透明導電性膜における長さとヘリシティーの影響
  • Author(s): 小森谷一記・浦野裕貴・山田道夫・ 前田優・長谷川正・赤阪健
  • Organizer: 日本化学会第5回関東支部大会
  • Place of Presentation: 東京農工大学（東京都）
• [Presentation] カーボンナノチューブのハロゲン化アルキルによる還元的化学修飾
  • Author(s): 斉藤和磨・千葉友莉子・赤松範久・山田道夫・前田優・長谷川正・赤阪健
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば国際会議場（茨城県）
• [Presentation] Dispersion, separation, and functionalization of single-walled carbon nanotubes
  • Author(s): 前田 優
  • Organizer: 筑波大学戦略イニシアティブ(A) 機能物質創製研究拠点第１回国際シンポジウム(招待講演)
  • Place of Presentation: 筑波大学（茨城県）
• [Book] 未来材料を創出するπ電子系の科学 (2013)
  • Author(s): 前田優、赤阪健カレントレビュー 、赤阪健、磯部寛之、岩澤伸治、山口茂弘
  • Publisher: 化学同人出版
• [Book] カレントレビュー No. 12「未来材料を創出するπ電子系の科学」 (2013)
  • Author(s): 前田 優
  • Total Pages: 190
  • Publisher: 化学同人出版
• [Book] Endohedral MetallofullereneFunctionalization (2012)
  • Author(s): Y. Maeda, T. Akasaka, S.N. Tagmatarchis
  • Publisher: Stanford Publishing
• [Book] Advances in Carbon Nanomaterials: Science and Applications (2012)
  • Author(s): Yutaka Maeda
  • Total Pages: 400
  • Publisher: Pan Stanford Publishing
• [Book] 炭素表面処理 (2012)
  • Author(s): 前田優、赤阪健、山田道夫、長谷川正
  • Total Pages: 394
  • Publisher: 技術情報協会
• [Book] 「カーボンナノチューブへのカルボキシ ル基導入とその官能基変換」「アミンによる単層カーボンナノチュー ブの分散と分離」 (2011)
  • Author(s): 前田 優、赤阪 健、山田道夫、長谷川正
  • Publisher: 技術情報協会出版
• [Remarks] 教員紹介ー自然科学系
  • URL: http://univinfo.u-gakugei.ac.jp/u-gakugei/hp/ymaeda1.html