Construction of hybrid supramolecular capsule through hydrogen bond and metal-ligand coordination bond, and dynamic guest encapsulation

• Project/Area Number: 19750111
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Functional materials chemistry
• Research Institution: Shizuoka University
• Principal Investigator: YAMANAKA Masamichi Shizuoka University, 理学部, 准教授 (10377715)
• Project Period (FY): 2007 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥3,710,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥510,000); Fiscal Year 2009: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2008: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2007: ¥1,500,000 (Direct Cost: ¥1,500,000)
• Keywords: 有機合成 / 超分子 / カプセル / 自己集合 / 水素結合 / 配位結合 / キャビタンド / 包接 / NMR

Research Abstract

Multifunctionalized C_<2v>-cavitand was synthesized in six steps from a tetrabromo cavitand. A 1:1 mixture of the synthesized cavitand and Pt(dppp)(OTf)_2 in CDCl_3 or CD_2Cl_2 quantitatively self-assemble into a supramolecular hybrid capsule through hydrogen bond and metal-ligand coordination bond. Cavity of the capsule is filled with triflate ion and penetrated alkyl groups of ureides. The capsule encapsulates a neutral guest molecule such as 4, 4'-diiodobiphenyl with the assistance of an anion. Encapsulation complex was identified by NMR technic. The kinetics of guest exchange is controllable by the amounts and/or types of anions or other influences such as the polarity of the solvent.

Research Products

• [Journal Article] Hybrid cavitand capsule with hydrogen bonds and metal-ligand coordination bonds: guest encapsulation with anion assistance (2009)
  • Author(s): Masamichi Yamanaka, Naoaki Toyoda, Kenji Kobayashi
  • Journal Title: Journal of the American Chemical Society Vol.131、No.29 Pages: 9880-9881
  • Peer Reviewed
• [Journal Article] Hybrid Cavitand Capsule with Hydrogen Bonds and Metal-ligand Coordination Bonds : Guest Encapsulation with Anion Assistance (2009)
  • Author(s): Masamichi Yamanaka, 他2名
  • Journal Title: Journal of the American Chemical Society 131 Pages: 9880-9881
  • Peer Reviewed
• [Journal Article] Chloroalkane Gel Formations by Tris-urea Low-molecular-weight Gelator under Various Conditions (2009)
  • Author(s): Masamichi Yamanaka, 他1名
  • Journal Title: The Journal of Organic Chemistry 74 Pages: 5390-5394
  • Peer Reviewed
• [Journal Article] Synthesis and estimation of gelation ability of C3-symmetry tris-urea compounds (2008)
  • Author(s): Masamichi Yamanaka, Tomoe Nakagawa, Ryohei Aoyama, Tomohiko Nakamura
  • Journal Title: Tetrahedron Vol.64、No.51 Pages: 11558-11567
  • Peer Reviewed
• [Journal Article] Synthesis and estimation of gelation ability of C_3-symmetry tris-urea compounds (2008)
  • Author(s): Masamichi Yamanaka, 他3名
  • Journal Title: Tetrahedron 64 Pages: 11558-11567
  • Peer Reviewed
• [Journal Article] Reversible sol-gel transition of a tris-urea gelator that responds to chemical stimuli (2007)
  • Author(s): Masamichi Yamanaka, Tomohiko Nakamura, Tomoe Nakagawa, Hideyuki Itagaki
  • Journal Title: Tetrahedron Letters Vol.48、No.51 Pages: 8990-8993
  • Peer Reviewed
• [Journal Article] Orientational isomerism controlled by the difference in electronic environments of a self-assembling heterodimeric capsule (2007)
  • Author(s): Kenji Kobayashi, Ryosuke Kitagawa, Yoshifumi Yamada, Masamichi Yamanaka, Takako Suematsu, Yoshihisa Sei, Kentaro Yamaguchi
  • Journal Title: The Journal of Organic Chemistry Vol.72、No.9 Pages: 3242-3246
  • Peer Reviewed
• [Journal Article] Reversible sol-gel transition of a tris-urea gelator that responds to chemical stimuli (2007)
  • Author(s): Kenji KobayaShi, 他6名
  • Journal Title: The Journal of Organic Chemistry 72 Pages: 3242-3246
  • Peer Reviewed
• [Journal Article] Reversible sol-gel transition of a tris-urea gelator that responds to chemical stimuli (2007)
  • Author(s): Masamichi Yamanaka, 他3名
  • Journal Title: Thtrahedron Letters 48 Pages: 8990-8993
  • Peer Reviewed
• [Journal Article] Chloroalkane gel formations by tris-urea low-molecular-weight gelator under various conditions
  • Author(s): Masamichi Yamanaka, Hiromitsu Fujii
  • Journal Title: The Journal of Organic Chemistry Vol.74、No.15 Pages: 5390-5394
  • Peer Reviewed
• [Presentation] 水素結合と配位結合を駆動力に自己集合するハイブリッド型超分子カプセル (2010)
  • Author(s): 河原田将史、小林健二、山中正道
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
• [Presentation] ハイブリッド型超分子カプセルにおける交換速度の解析 (2010)
  • Author(s): 足立博文、豊田直晃、小林健二、山中正道
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
• [Presentation] C_<2v>対称キャビタンドの合成 (2009)
  • Author(s): 河原田将史、豊田直晃、小林健二、山中正道
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学(船橋)
  • Year and Date: 2009-03-29
• [Presentation] 異種非共有結合を介した超分子カプセルによる動的ゲスト分子包接 (2009)
  • Author(s): 豊田直晃、小林健二、山中正道
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学(船橋)
  • Year and Date: 2009-03-27
• [Presentation] 異種非共有結合を介した超分子カプセルによる動的ゲスト分子包接 (2009)
  • Author(s): 山中正道、豊田直晃、小林健二
  • Organizer: 第5回ホスト・ゲスト化学シンポジウム
  • Place of Presentation: 宇都宮大学(栃木)
• [Presentation] C2v対称キャビタンドの合成 (2009)
  • Author(s): 河原田将史、豊田直晃、小林健二、山中正道
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学(千葉)
• [Presentation] 異種非共有結合を介した超分子カプセルによる動的ゲスト分子包接 (2009)
  • Author(s): 豊田直晃、小林健二、山中正道
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学(千葉)
• [Presentation] C_<2v>対称キャビタンドの自己集合による超分子カプセルの構築とゲスト分子の包接 (2008)
  • Author(s): 豊田直晃、小林健二、山中正道
  • Organizer: 第19回基礎有機化学討論会
  • Place of Presentation: 大阪大学(大阪)
  • Year and Date: 2008-10-05
• [Presentation] C2v対称キャビタンドの自己集合による超分子カプセルの構築とゲスト分子の包接 (2008)
  • Author(s): 豊田直晃、小林健二、山中正道
  • Organizer: 第19回基礎有機化学討論会
  • Place of Presentation: 大阪大学(大阪)
• [Presentation] 配位部位と水素結合部位を有するC2v対称キャビタンドの合成 (2008)
  • Author(s): 豊田直晃、小林健二、山中正道
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学(東京)
• [Presentation] 官能基化非対称キャビタンドの合成とその性質 (2007)
  • Author(s): 豊田直晃、小林健二、山中正道
  • Organizer: 第37回構造有機化学討論会
  • Place of Presentation: 北海道大学(北海道)
• [Remarks]
  • URL: http://www.ipc.shizuoka.ac.jp/~smyaman/welcome.html