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Alteration of Organic Synthetic Processes Using Organic Zeolites in Water

Research Project

Project/Area Number 13555220
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 触媒・化学プロセス
Research InstitutionKyoto University

Principal Investigator

AOYAMA Yasuhiro  Kyoto University, Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (00038093)

Co-Investigator(Kenkyū-buntansha) SANDO Shinsuke  Kyoto University, Graduate School of Engineering, Research Associate, 大学院・工学研究科, 助手 (20346084)
ENDO Ken  Akita University, Faculty of Resource Engineering, Lecturer, 工学資源学部, 講師 (70304730)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥13,500,000 (Direct Cost: ¥13,500,000)
Fiscal Year 2003: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2002: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2001: ¥7,500,000 (Direct Cost: ¥7,500,000)
Keywordsorganic zeolite / enolization / solid catalyst / self-complementarity / methane adsorption / crystal engineering / antharacene / glycocluster / 多孔体 / 水素結合 / ポアサイズ / 遺伝子診断 / 自己切断 / プローブ / 自己相補的ホスト / 包接 / X線結晶解析 / 結晶構造 / 多孔質 / ジルコニウム / 糖の異性化 / ホスト-ゲスト / 超臨界流体
Research Abstract

We investigated the microporocity, guest-binding properties, and catalytic behaviors of "organic zeolites" based on anthracene-bisresorcinol derivatives. The major achievements are as follows.
(1) Lanthanum-containing organic zeolites catalyze various reactions of carbonyl substrates which proceed via enolate intermediates. This is, however, not the case for such reactions as carbonylation of ketones with CO_2 and isomerization of sugars, in which the chelate-type products show strong affinity to the metallic center to prohibit turnover of the catalysts.
(2) Lanthanum complexes of triphenylphosphine was used to network various, heavy metals such as Pd(II), Ru(II), Rh(II), and Pt(II) to give microporous materials. They are capable of promoting, characteristic reactions of these metals such as. coupling but only in a stoichiometric manner ; this is because reoxidation of reduced, metal centers is still a problem.
(3) Acridine-bisresorcinol derivatives serve as a "self-complementary" building blocks in which the nitrogen acts as a kind of "guest" for the resorcinol moiety to give coordinatively saturated and robust microporous material. Benzene as a guest can be removed without changing the crystal structure significantly.
(4) Anthracene-bis(isophtalic acid) gives rise to a remarkably robust H-bonded network capable to reversible adsorption-desorption of methane. The crystal structure of genuine microporopus crystal structure was revealed.
(5) Attempts were also made to utilize glycoclusters as a source of organic zeolites stable in water. The calix[4]resorcarene-based macrocyclic glycoclusters encapsulate plasmid DNA in a size-and number-controlled manner to give artificial "glycovirus" of a size of 50 nm.

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] T.Dewa, T.Saiki, Y.Aoyama: "Enolization and Aldol Reactions of Ketone with a La3+-Immobilized Organic Solid in Water. A Microporous Enolase Mimic"J.Am.Chem.Soc.. 123. 502-503 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Tanaka, K.Endo, Y.Aoyama: "Stacked Porphyrin Arrays from Hydrogen-Bonded Porphyrin-Resorcinol 1D Chains"Bull.Chem.Soc.Jpn.. 74. 907-916 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Naito, Y.Sasaki, T.Dewa, Y.Aoyama, Y.Okahata: "Effect of Solvation on Induced-Fit Molecular Recognition in Supercrutical Fluid to Organic Crystals Immobilized on a Quartz Crystal Microbalance"J.Am.Chem.Soc.. 123. 11037-11041 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Tanaka, T.Tasaki, Y.Aoyama: "Acridinylresorcinol as a Self-Complementary Building Block of Robust Hydrogen-Bonded 2D Nets with Coordinative Saturation. Preservation of Crystal Structures upon Guest-Alteration, Guest Removal, and Host Modification"J.Am.Chem.Soc.. 124. 12453-12462 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Ken Endo, Yoshihiko Kondo, Yasuhiro Aoyama, Fumio Hamada: "Guest-Binding Properties of Functionally Porous Crystal Based on Metal Complex of p-tert Butylcalix[6]arene"Tetrahedron Lett.. 44. 1355-1358 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] O.Hayashida, K.Mizuki, K.Akagi, A.Matsuo, T.Kanamori, T.Nakai, S.Sando, Y.Aoyama: "Macrocyclic Glycoclusters. Self-Aggregation and Phosphate-Induced Agglutination Behaviors of Calix[4]resorcarene-Based Quadruple-Chain Amphiphile with a Huge Oligosaccharide Pool"J.Am.Chem.Soc.. 125. 594-601 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Aoyama, T.Kanamori, T.Nakai, T.Sasaki, S.Horiuchi, S.Sando, T.Niidome: "Artificial Viruses and Their Application to Gene Delivery. Size-Controlled Gene Coating with Glycocluster Nanoparticles"J.Am.Chem.Soc.. 125. 3455-3457 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Nakai, T.Kanamori, S.Sando, Y.Aoyama: "Remarkably Size-Regulated Cell Invasion by Artificial Viruses. Saccharide-Dependent Self-Aggregation of Glycoviruses and Its Consequences in Glycoviral Gene Delivery"J.Am.Chem.Soc.. 125. 8465-8475 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuhiro Aoyama: "Macrocyclic Glycoclusters. From Amphiphiles Through Nanoparticles to Glycoviruses"Chem.Eur.J.. 10. 588-593 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 青山安宏: ""有機ゼオライト"、「ナノマテリアルアルハンドブック」"エヌ・ティー・エス(印刷中). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Dewa, T.Saiki, Y.Aoyama: "Enolization and Aldol Reactions of Ketone with a La^<3+>-Immobilized Organic Solid in Water. A Microporous Enolase Mimic"J.Am.Chem.Soc.. 123. 502-503 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Toshihiro Tanaka, Ken Endo, Yasuhiro Aoyama: "Stacked Porphyrin Arrays from Hydrogen-Bonded Porphyrin-Resorcinol 1D Chains"Bull.Chem.Soc.Jpn.. 74. 907-916 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Masanobu Naito, Yusuke Sasaki, Takehisa Dewa, Yasuhiro Aoyama, Yoshio Okahata: "Effect of Solvation on Induced-Fit Molecular Recognition in Supercrutical Fluid to Organic Crystals Immobilized on a Quartz Crystal Microbalance"J.Am.Chem.Soc.. 123. 11037-11041 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Toshihiro Tanaka, Takashi Tasaki, Yasuhiro Aoyama: "Acridinylresorcinol as a Self-Complementary Building Block of Robust Hydrogen-Bonded 2D Nets with Coordinative Saturation. Preservation of Crystal Structures upon Guest-Alteration, Guest Removal, and Host Modification"J.Am.Chem.Soc.. 124. 12453-12462 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Ken Endo, Yoshihiko Kondo, Yasuhiro Aoyama, Fumio Hamada: "Guest-Binding Properties of Functionally Porous Crystal Based on Metal Complex of p-tert-Butylcalix[6]arene"Tetrahedron Lett.. 44. 1355-1358 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Osamu Hayashida, Keiji Mizuki, Kazuyuki Akagi, Aki Matsuo, Takuya Kanamori, Takuya Nakai, Shinsuke Sando, Yasuhiro Aoyama: "Macrocyclic Glycoclusters. Self-Aggregation and Phosphate-Induced Agglutination Behaviors of Calix[4]resorcarene-Based Quadruple-Chain Amphiphile with a Huge Oligosaccharide Pool"J.Am.Chem.Soc.. 125. 594-601 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuhiro Aoyama, Takuya Kanamori, Takashi Nakai, Takashi Sasaki, Shohei Horiuchi, Shinsuke Sando, Takuro Niidome: "Artificial Viruses and Their Application to Gene Delivery. Size-Controlled Gene Coating with Glycocluster Nanoparticles"J.Am.Chem.Soc.. 125. 3455-3457 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Takashi Nakai, Takuya Kanamori, Shinsuke Sando, Yasuhiro Aoyama: "Remarkably Size-Regulated Cell Invasion by Artificial Viruses. Saccharide-Dependent Self-Aggregation of Glycoviruses and Its Consequences in Glycoviral Gene Delivery"J.Am.Chem.Soc.. 125. 8465-8475 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuhiro Aoyama: "Macrocyclic Glycoclusters. From Amphiphiles through Nanoparticles to Glycoviruses"Chem.Eur.J.. 10. 588-593 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Endo, Y.Kondo, Y.Aoyama, F.Hamada: "Guest-Binding Properties of Functionally Porous Crystal Based on Metal Complex of p-tert-Butylcalix[6]arene"Tetrahedron Lett.. 44. 1355-1358 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] O.Hayashida, K.Mizuki, K.Akagi, A.Matsuo, T.Kanamori, T.Nakai, S.Sando, Y.Aoyama: "Macrocyclic Glycoclusters. Self-Aggregation and Phosphate-Induced Agglutination Behaviors of Calix[4]resorcarene-Based Quadruple -Chain Amphiphile with a Huge Oligosaccharide Pool"J.Am.Chem.Soc.. 152・2. 594-601 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Aoyama, T.Kanamori, T.Nakai, T.Sasaki, S.Horiuchi, S.Sando, T.Niiodme: "Artificial Viruses and Their Application to Gene Delivery. Size-Controlled Gene Coating with Glycocluster Nanoparticles"J.Am.Chem.Soc.. 125・12. 3455-3457 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Nakai, T.Kanamori, S.Sando, Y.Aoyama: "Remarkably Size-Regulated Cell Invasion by Artificial Viruses. Saccharide-Dependent Self-Aggregation of Glycoviruses and Its Consequences in Glycoviral Gene Delivery"J.Am.Chem.Soc.. 125・28. 8465-8475 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] S.Sando, T.Sasaki, K.Kanatani, Y.Aoyama: "Amplified Nuclein Acid Sensing Using Programmed Self-Cleaving DNAzyme"J.Am.Chem.Soc.. 125・51. 15720-15721 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Aoyama: "Macrocyclic Glycoclusters. From Amphiphiles through Nanoparticles to Glycoviruses"Chem.Eur.J.. 10・3. 588-593 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 青山安宏: "ナノマテリアルアルハンドブック(有機ゼオライト)"エヌ・ティー・エス(印刷中). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Tanaka, T.Tasaki, Y.Aoyama: "Acridinylresorcinol as a Self-Complementary Building Block of Robust Hydrogen=bonded 2D Nets with Coordinatively Saturation. Preservation of Crystal Structures upon Guest Removal, Guest Alteration, and Host Modification"J.Am.Chem.Soc.. 124・42. 12453-12462 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Endo, Y.Kondo, Y.Aoyama, F.Hamada: "Guest-Binding Properties of Functionally Porous Crystal Based on Metal Complex of p-tert-Butylthiacalix[6]arene"Tetrahedron Lett. 6(印刷中). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] O.Hayashida, K.Mizuki, K.Akagi, A.Matsuo T.Kanamori, T.Nakai, S.Sando, Y.Aoyama: "Macrocyclic Glycoclusters. Self-Aggregation and Phosphate-Induced Agglutination Behaviors of Calix[4]resorcarene-Based Quadruple-Chain Amphiphiles with a Huge Oligosaccharide Pool"J.Am.Chem.Soc. 125・2. 594-601 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Aoyama, T.Kanamori, T.Nakai, T.Sasaki, S.Horiuchi, S.Sando, T.Niidome: "Artificial Viruses and Their Application to Gene Delivery. Size-Controlled Gene Coating with Glycocluster nanoparticles"J.Am.Chem.Soc.. 125(印刷中). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Takehisa DEWA, Toshiyuki SAIKI, Yasuhiro AOYAMA: "Enolization and Aldol Reactions of Ketone with a La-Immobilized Organic Solids in Water. A Microporous Enolase Mimic"J.Am.Chem.Soc.. 123・3. 502-503 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Osamu HAYASHIDA, Aki MATSUO, Yasuhiro AOYAMA: "Macrocyclic Saccharide Bundles as a New Type of Firm DNA Binders"Chem.Lett.. 3. 272-273 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Toshihiro TANAKA, Ken ENDO, Yasuhiro AOYAMA: "Stacked Porphyrin Arrays from Hydrogen-Bonded Porphyrin-Resorcinol 1D Chains Bull. Chem. Soc. Jpn."Bull.Chem.Soc.Jpn.. 74・5. 907-916 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Masanobu NAITO, Yusuke SASAKI, Takehisa DEWA, Yasuhiro AOYAMA, Yoshio OKAHATA: "Effect of Solvation on Induced-Fit Molecular Recognition in Supercritical Fluid to Organic Crystals Immobilized on a Quartz Crystal Microbalance"J.Am.Chem.Soc.. 123・44. 11037-11041 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 林田修, 青山安宏: "糖鎖分子の設計と生理機能"学会出版センター. 94-100 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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