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Application of Artificial Polyamides, Having Cyclobutane Rings in the Main Chain, as Chiral Stationary Phases for Hplc

Research Project

Project/Area Number 01850200
Research Category

Grant-in-Aid for Developmental Scientific Research (B).

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionThe University of Tokyo

Principal Investigator

SAIGO Kazuhiko  The University of Tokyo, Faculty of Engineering, Associate Professor, 工学部, 助教授 (80016154)

Co-Investigator(Kenkyū-buntansha) TACHIBANA Kouzou  Daicel Chemical Industries, LTD., Research Associate, セパレーションシステム, 研究員
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥4,800,000 (Direct Cost: ¥4,800,000)
Fiscal Year 1990: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1989: ¥2,700,000 (Direct Cost: ¥2,700,000)
KeywordsPhotodimerization / Optical Resolution / Ring-Opening Polyaddition / Alkaline Depolymerization / Optically Active Polyamides / Chiral Stationary Phases for HPLC / Odd-Even Discrimination / Odered Conformation
Research Abstract

The phenolic hydroxyl groups in optically active polyamides, which consist of anti head-to-head coumarin dimer, were easily carbamoylated with several kinds of isocyanates in high yield and conversion. HPLC coumns were prepared by coating the polyamides on silica gel surface. The carbamoylated polyamides showed a chiral recognition ability for the racemates, which could not be recognized by the parent polyamides. Consequently, the carbamoylated and parent polyamides showed complementary recognition ability.
The chiral recognition ability of polyamides, consisting of anti head-to-head coumarin dimer and alpha, omega-alkanediamine, depended on the methylene number of the diamine component and showed odd-even dscrimination. The X-ray diffraction and DSC analyses revealed that the chiral recognition ability appeared only for the polyamides, which could crystallize on the surface of silica gel and that the higher crystallinity resulted in the higher chiral recognition ability. This result is … More the first example for the elucidation of the correlation between chiral recognition ability, crystallinity, and odd-even discrimination.
Polyamides, derived from anti head-to-head umbelliferone dimer, showed steep decrease of their viscosity in an alkaline solution, whereas polyamides consisting of anti head-to-head coumarin dimer were rather stable in an alkaline solution. This phenomenon was found to result from the scission of the main chian via a quinoid from of dihydroxyphenyl groups in the side chain.
Anti head-to-head umbelliferone dimer was successfully resolved into enantiomers with high optical purities. The ring-opening polyaddition reaction of the optically active dimer with diamines proceeded very smoothly to give the corresponding, optically active polyamides. Some of them existed in ordered conformation in a solution and/or film state. The polyamides, however, unfortunately showed no chiral recognition ability, which would come from the strong hidrogen bonding between the hydroxyl group at C7 and a solute. Less

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] K.SAIGO: "Preparation,Chiroptical Properties,and Chiral Recognition Ability of Carbamoylated Polyamides Having (-)ーAnti HeadーtoーHead Coumarin Dimen Component" Chem.Lett.337-340 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 西郷 和彦: "光〔2+2〕付加環化・開裂と高分子" 有機合成化学協会誌. 47. 1006-1016 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K.SAIGO: "Optically Active Polyamides Consisting of Anti HeadーtoーHead coumarin Dimer and α,ωーAlkamediamine.OddーEven Discrimination in Chiral Recognition Ability" Macromolecules. 23. 2830-2836 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K.SAIGO: "Synthesis and Properties of Polyamides Having Anti HeadーtoーHead Umbelliferon Dimer as a Component" Macromolecules. 23. 3722-3729 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K.SAIGO: "Future Opportunities in Catalytic and Separation Technology" Elsevier, 378(13) (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K. Saigo: "Preparation, Chiral Properties, and Chiral Recognition Ability of Carbamoylated Polyamides Having (-)-Anti Head-to-Head Coumarin Dimer Component" Chem. Lett.337-340 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K. Saigo: "Optically Active Polyamides Consisting of Anti Head-to-Head Coumarin Dimer and alpha, omega-Alkanediamine. Odd-Even Discrimination in Chiral Recognition Ability Depending on the Methylene Number of the Diamine Component and Correlation between the Ability and Crystallizability" Macromolecules. 23. 2830-2836 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K. Saigo: "Synthesis and Properties of Polyamides Having Anti Head-to-Head Umbelliferone Dimer as a Component" Macromolecules. 23. 3722-3729 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K. Saigo: "Future Opportunities in Catalytic and Separation Technology" Elsevier. 378 (13). (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K.SAIGO: "Optically Active Polyamide Comsisting of Anti HeadーtoーHead Coumarin Dimer and α,wーAlkanediamine.OddーEven Discrimination in Chiral Recognition Ability" Macromolecules. 23. 2830-2836 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.SAIGO: "Synthesis and Properties of Polyamides Having Anti HeadーtoーHead Umbelliferone Dimer as a Component" Macromolecules. 23. 3722-3729 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.SAIGO: "Future Opportunities in Catalytic and Sepavation Technology (in part)" Elsevier, 378(13) (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Kazuhiko SAIGO: "Preparation,Chiroptical Properties,and Chiral Recognition Abclity of Carbamoylated Polyamides Having(-)-Anti Head-to-Head Coumarin Dimer Component" 337-340 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kazuhiko SAIGO: "Optically Active Polyamides Consisting of Anti Head-to-Head Coumarin Dimer and α,ω-Alkanediamine,Odd-Even Discrimination in Chiral Recognition Abilcty" Macromolecules. 23. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kazuhiko SAIGO: "Synthesis and Properties of Polyamides Having Anti Head-to-Head Umbelliferane Dimer asa Component" Macromolecules. 23. (1990)

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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