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A Novel Strategy of Absolute Asymmetric Synthesis via Spin Coating

Research Project

Project/Area Number 17350044
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

AIDA Takuzo  The University of Tokyo, Department of Chemistry and Biotechnology, School of Engineering, Professor, 大学院工学系研究科, 教授 (00167769)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥14,700,000 (Direct Cost: ¥14,700,000)
Fiscal Year 2006: ¥5,400,000 (Direct Cost: ¥5,400,000)
Fiscal Year 2005: ¥9,300,000 (Direct Cost: ¥9,300,000)
KeywordsChirality / Absolute Asymmetric Synthesis / Porphyrin / Dendrimer / Spin-coat / Optical Activity / Supramolecular Chemistry
Research Abstract

'Absolute asymmetric synthesis', which produces asymmetric compounds without using a chiral catalyst, has attracted much interest in various research fields, in the purpose of establishment of an effective methodology for synthesis of the asymmetric compounds as well as investigation of an origin of chiral symmetry breaking in nature. A successful example so far reported in the absolute asymmetric synthesis has been developed by utilization of the chiral crystals, where certain achiral compounds form a one-handed helical alignment in the crystal packing. However, this strategy has been only allowed to utilize for special substrates. On the other hands, asymmetric photoreactions using circularly polarized lights have been also believed as an effective methodology of the absolute asymmetric synthesis. However, in this procedure, we have to make a specially designed polarized light generator, and further, the chiral symmetry breaking occurs usually in low yield. With this background, we have studied a possible absolute asymmetric synthesis using physical chiral stimuli such as spin-coating and stirring of the solution. Mechanical control of the molecular chirality is a big challenge of synthetic chemistry, which allows selective synthesis of one of the enantiomers by rotating direction (clockwise or counterclockwise) of the disk or stirring bar. To date, no related achievements have been reported for this subject, we have expected universal utilization of our research achievements in the chiral sciences. In the present study, we have succeeded in finding some interesting molecular events, which highly advances the modern chiral sciences.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (39 results)

All 2007 2006 2005

All Journal Article (39 results)

  • [Journal Article] Crystallographic and Chiroptical Studies on Tetraarylferrocenes for Use as Chiral Rotary Modules for Molecular Machines2007

    • Author(s)
      Takahiro Muraoka, et al.
    • Journal Title

      Chem. Eur. J. 13

      Pages: 1724-1724

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Catalysis of a Peptidic Micellar Assembly Covalently Immobilized within Mesoporous Silica Channels : Importance of Amphiphilic Spatial Design2007

    • Author(s)
      Wataru Otani, et al.
    • Journal Title

      Chem. Eur. J. 13

      Pages: 1731-1731

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Reversible Operation of Chiral Molecular Scissors by Redox and UV Light2007

    • Author(s)
      Takahiro Muraoka, et al.
    • Journal Title

      Chem. Commun.

      Pages: 1441-1441

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Metalloporphyrin Hosts for Supramolecular Chemistry of Fullerenes2007

    • Author(s)
      Kentaro Tashiro, et al.
    • Journal Title

      Chem. Soc. Rev. 36

      Pages: 189-189

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Chiroptical Sensing of Asymmetric Hydrocarbons using a Homochiral Supramolecular Box from a Bismetalloporphyrin Rotamer2007

    • Author(s)
      Junko Aimi, et al.
    • Journal Title

      Angew. Chem. Int. Ed. 46

      Pages: 2031-2031

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Crystallographic and Chiroptical Studies on Tetraarylferrocenes for Use as Chiral Rotary Modules for Molecular Machines2007

    • Author(s)
      Takahiro Muraoka, Kazushi Kinbara, Atsushi Wakamiya, Shigehiro Yamaguchi, Takuzo Aida
    • Journal Title

      Chem.Eur.J. 13

      Pages: 1724-1730

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Catalysis of a Peptidic Micellar Assembly Covalently Immobilized within Mesoporous Silica Channels : Importance of Amphiphilic Spatial Design2007

    • Author(s)
      Wataru Otani, Kazushi Kinbara, Quigmin Zhang, Katsuhiko Ariga, Takuzo Aida
    • Journal Title

      Chem.Eur.J. 13

      Pages: 1731-1736

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Reversible Operation of Chiral Molecular Scissors by Redox and UV Light2007

    • Author(s)
      Takahiro Muraoka, Kazushi Kinbara, Takuzo Aida
    • Journal Title

      Chem.Commun.

      Pages: 1441-1443

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Metalloporphyrin Hosts for Supramolecular Chemistry of Fullerenes2007

    • Author(s)
      Kentaro Tashiro, Takuzo Aida
    • Journal Title

      Chem.Soc.Rev. 36

      Pages: 189-197

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Chiroptical Sensing of Asymmetric Hydrocarbons using a Homochiral Supramolecular Box from a Bismetalloporphyrin Rotamer2007

    • Author(s)
      Junko Aimi, Kazumasa Oya, Akihiko Tsuda, Takuzo Aida
    • Journal Title

      Angew.Chem., Int.Ed. 46

      Pages: 2031-2035

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Chiroptical Sensing of Asymmetric Hydrocarbons using a Homochiral Supramolecular Box from a Bismetalloporphyrin Rotamer2007

    • Author(s)
      Junko Aimi, Kazumasa Oya, Akihito Tsuda, Takuzo Aida
    • Journal Title

      Angew. Chem. Int. Ed. 46

      Pages: 2031-2031

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Crystallographic and Chiroptical Studies on Tetraarylferrocenes for Use as Chiral Rotary Modules for Molecular Machines2007

    • Author(s)
      Takahiro Muraoka, Kazushi Kinbara, Atsushi Wakamiya, Shigehiro Yamaguchi, Takuzo Aida
    • Journal Title

      Chem. Eur. J. 13

      Pages: 1724-1724

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Metalloporphyrin Hosts for Supramolecular Chemistry of Fullerenes2007

    • Author(s)
      Kentaro Tashiro, Takuzo Aida
    • Journal Title

      Chem. Soc. Rev. 36

      Pages: 189-189

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Mechanical Twisting of a Guest by a Photoresponsive Host2006

    • Author(s)
      Takahiro Muraoka, et al.
    • Journal Title

      Nature 440

      Pages: 512-512

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Semibiological Molecular Machine with an Impremented "AND" Logic Gate for Regulation of Protein Folding2006

    • Author(s)
      Shinichi Muramatsu, et al.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 3764-3764

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Self-Regulartory Host in an Oscillatory Guest Motion : Complexatioin of Fullerenes with a Short-Spaced Cyclic Dimer of an Organorhodium Porphyrin2006

    • Author(s)
      Ayako Ouchi, et al.
    • Journal Title

      Angew. Chem. Int. Ed. 45

      Pages: 3542-3542

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Hermaphroditic Chirality" of a D_2-Symmetric Saddle-Shaped Porphyrin in Multicomponent Spontaneous Optical Resolution : Inclusion Cocrystals with Double-Helical Porphyrin Arrays2006

    • Author(s)
      Yukitami Mizuno, et al.
    • Journal Title

      Angew. Chem. Int. Ed. 45

      Pages: 3786-3786

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Self-Locking Molecule Operative with a Photoresponseive Key2006

    • Author(s)
      Takahiro Muraoka, et al.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 11600-11600

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Sensing of Chiral Fullerenes by a Cyclic Host with an Asymmetrically Distorted π-Electronic Component2006

    • Author(s)
      Yoshiaki Shoji, et al.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 10690-10690

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Mechanical Twisting of a Guest by a Photoresponsive Host2006

    • Author(s)
      Takahiro Muraoka, Kazushi Kinbara, Takuzo Aida
    • Journal Title

      Nature 440

      Pages: 512-515

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Semibiological Molecular Machine with an Impremented "AND" Logic Gate for Regulation of Protein Folding2006

    • Author(s)
      Shinichi Muramatsu, Kazushi Kinbara, Hideki Taguchi, Noriyuki Ishii, Takuzo Aida
    • Journal Title

      J.Am.Chem.Soc. 128

      Pages: 3764-3769

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Self-Regulartory Host in an Oscillatory Guest Motion : Complexatioin of Fullerenes with a Short-Spaced Cyclic Dimer of an Oreanorhodium Pornhvrin2006

    • Author(s)
      Ayako Ouchi, Kentaro Tashiro, Kentaro Yamaguchi, Takeshi Akasaka, Takuzo Aida
    • Journal Title

      Angew.Chem., Int.Ed. 45

      Pages: 3542-3546

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] "Hermaphroditic Chirality" of a D2-Symmetric Saddle-Shaped Porphyrin in Multicomponent Spontaneous Optical Resolution : Inclusion Cocrvstals with Double-Helical Pornhvrin Arrays2006

    • Author(s)
      Yukitami Mizuno, Md.Akhtarul Alam, Akihiko Tsuda, Kazushi Kinbara, Kentaro Yamaguchi, Takuzo Aida
    • Journal Title

      Angew.Chem., Int.Ed. 45

      Pages: 3786-3790

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Self-Locking Molecule Operative with a Photoresponseive Key2006

    • Author(s)
      Takahiro Muraoka, Kazushi Kinbara, Takuzo Aida
    • Journal Title

      J.Am.Chem.Soc. 128

      Pages: 11600-11605

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Sensing of Chiral Fullerenes by a Cyclic Host with an Asymmetrically Distorted π-Electronic Component2006

    • Author(s)
      Yoshiaki Shoji, Kentaro Tashiro, Takuzo Aida
    • Journal Title

      J.Am.Chem.Soc. 128

      Pages: 10690-10691

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Sensing of Chiral Fullerenes by a Cyclic Host with an Asymmetrically Ditorted π-Electronic Component2006

    • Author(s)
      Yoshiaki Shoji, kentaro Tashiro, Takuzo Aida
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 10690-10690

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Hermaphoroditic Chirality"of a D_2-Symmetric Saddle-Shaped Porphyrin in Multicomponent Spontaneous Optical Resolution : Inclusion Cocrystals with Double-Helical Porphyrin Arrays2006

    • Author(s)
      Yukitami Mizuno, Md, Akhtarul Alam, Akihiko Tsuda, Kazushi Kinbara, Kentaro Yamaguchi, Takuzo Aida
    • Journal Title

      Angew. Chem. Int. Ed 45

      Pages: 3786-3786

    • Related Report
      2006 Annual Research Report
  • [Journal Article] A Self-Locking Molecule Operative with a Photoresponseive Key2006

    • Author(s)
      Takahiro Muraoka, Kazushi Kinbara, Takuzo Aida
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 11600-11600

    • Related Report
      2006 Annual Research Report
  • [Journal Article] "Hermaphroditic Chirality" of a D_2-Symmetric Saddle-Shaped Porphyrin in Multicomponent Spontaneous Optical Resolution : Inclusion Cocrystals with Double-Helical Porphyrin Arrays2006

    • Author(s)
      Yukitami Mizuno, Md.Akhtarul Alam, Akihiko Tsuda, Kazushi Kinbara, Kentaro Yamaguchi, Takuzo Aida
    • Journal Title

      Angewandte Chemie International Edition 45(印刷中)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Towards Intelligent Molecular Machines : Directed Motions of Biological and Artificial Molecules and Assemblies2005

    • Author(s)
      Kazushi Kinbara, et al.
    • Journal Title

      Chem. Rev. 105

      Pages: 1377-1377

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Rewritable Phosphorescent Paper by the Control of Competing Kinetic and Thermodynamic Self-Assembling Events2005

    • Author(s)
      Akihiro Kishimura, et al.
    • Journal Title

      Nature Materials 4

      Pages: 546-546

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Cyclic Dimer of a Fused Porphyrin Zinc Complex as a Novel Host with Two π-Electronically Coupled Binding Sites2005

    • Author(s)
      Hiroshi Sato, et al.
    • Journal Title

      Chem. Commun.

      Pages: 2324-2324

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Planar or Perpendicular? Conformational Preferences of π-Conjugated Metalloporphyrin Dimer and Trimer in Supramolecular Tubular Arrays2005

    • Author(s)
      Akihiko Tsuda, et al.
    • Journal Title

      Angew. Chem., Int. Ed. 44

      Pages: 4884-4884

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Positive Heterotropic Cooperativity for Selective Guest Binding via Electronic Communications through a Fused Zinc Porphyrin Array2005

    • Author(s)
      Hiroshi Sato, et al.
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 13086-13086

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Towards Intelligent Molecular Machines : Directed Motions of Biological and Artificial Molecules and Assemblies2005

    • Author(s)
      Kazushi Kinbara, Takuzo Aida
    • Journal Title

      Chem.Rev. 105

      Pages: 1377-1400

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Rewritable Phosphorescent Paper by the Control of Competing Kinetic and Thermodynamic Self-Assembling Events2005

    • Author(s)
      Akihiro Kishimura, Takashi Yamashita, Kentaro Yamaguchi, Takuzo Aida
    • Journal Title

      Nature Materials 4

      Pages: 546-549

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Cyclic Dimer of a Fused Porphyrin Zinc Complex as a Novel Host with Two π-Electronically Coupled Binding Sites2005

    • Author(s)
      Hiroshi Sato, Kentaro Tashiro, Atsuhiro Osuka, Takuzo Aida
    • Journal Title

      Chem.Commun

      Pages: 2324-2326

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Planar or Perpendicular? Conformational Preferences of π-Conjugated Metalloporphyrin Dimer and Trimer in Supramolecular Tubular Arrays2005

    • Author(s)
      Akihiko Tsuda, Haifeng Hu, Ryo Tanaka, Takuzo Aida
    • Journal Title

      Angew.Chem., Int.Ed. 44

      Pages: 4884-4888

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Positive Heterotropic Cooperativity for Selective Guest Binding via Electronic Communications through a Fused Zinc Pornhvrin Array2005

    • Author(s)
      Hiroshi Sato, Kentaro Tashiro, Hideyuki Shinmori, Atsuhiro Osuka, Yasujiro Murata, Koichi Komatsu, Takuzo Aida
    • Journal Title

      J.Am.Chem.Soc. 127

      Pages: 13086-13087

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary

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Published: 2005-04-01   Modified: 2016-04-21  

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