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Synthesis of Ring-Accumulated Polymers based on Arrangement of Diketopiperazines

Research Project

Project/Area Number 17550117
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Polymer chemistry
Research InstitutionKyoto University

Principal Investigator

SANDA Fumio  Kyoto University, Graduate School of Engineering, Associate Professor, 工学研究科, 助教授 (70262318)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2006: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 2005: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsDiketopiperazine / Chiral / Hierarchical Structure / Polycondensation / Aspartic Acid / Glutamic Acid / Hydrogen Bond / πStacking / 配列 / 環集積 / ポリマー / 会合 / 超分子
Research Abstract

The objectives of the present research include asymmetric selectivity during polymerization, formation of higher order structure and chiral recognition based on regulated arrangement of diketopiperazines, and investigation of possibility of the formed polymers as nano and bio-compatible materials.
First, synthesis of novel compounds containing two diketopiperazine units was carried out. In the early stage of the research, diketopiperazine derivatives with two free amide N-H moieties were examined, but isolation of the compounds was difficult due to the low solubility. Therefore, diketopiperazine derivatives with one N-H and one N-CH_3 moieties were synthesized to enhance the solubility, some of which exhibited liquid crystalline property. It was suggested that they form a hierarchical structure.
Second, synthesis and polycondensation of aspartic acid-and glutamic acid-based diketopiperazines with α,α-dibromoxylenes and diamines were carried out. At the moment, the obtained polymers with the weight-average molecular weight of several thousands exhibited no evidence to take a higher order structure. It is considered that the low molecular weights are responsible to the poor solubility. Incorporation of long alkyl chains is desirable in the future. Utilization of π-stacking, hydrophobic interaction, and ionic interactions as well as hydrogen bonding interaction is expected to induce higher order structure.

Report

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

    (2 results)

All 2007 Other

All Journal Article (2 results)

  • [Journal Article] Polycondensation of Diketopiperazine-based Dicarboxylic Acids with Diamines and Dibromoxylenes2007

    • Author(s)
      Kayo Terada, Fumio Sanda, Toshio Masuda
    • Journal Title

      Journal of Macromolecular Science, Part A : Pure and Applied Chemistry 44

      Pages: 789-794

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Polycondensation of Diketopiperazine-based Dicarboxylic Acids with Diamines and Dibromoxylenes

    • Author(s)
      Kayo Terada, Fumio Sanda, Toshio Masuda
    • Journal Title

      Journal of Macromolecular Science, Part A : Pure and Applied Chemistry (印刷中)

    • Related Report
      2006 Annual Research Report

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

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