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2007 Fiscal Year Final Research Report Summary

Development of self-organized materials using anion-controllable interaction

Research Project

Project/Area Number 18550116
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionSaitama University

Principal Investigator

KUBO Yuji  Saitama University, Graduate School of Science and Engineering, Associate professor (80186444)

Project Period (FY) 2006 – 2007
Keywordsphenylboronic acid / alizarin / self-organization / anion sensor / molecular capsule / Zn^<II>-dipycolylamine / cyclotricatechylene / calixarene
Research Abstract

We briefly summarized the research on the title. 1) Self-organized anion sensors with alizarins as a reporter As our on-going project for developing chemosensors for the detection of chemically and biologically important anions, we synthesized several phenylboronic acid derivatives which act as a receptor moiety. The combination of it with catecholcontained alizarins as a reporter unit allows us to propose self-organized sensor systems. A self-organized fluorescent sensor consisting of alizarin and o-aminomethylphenylboronic acid shows a highly selective fluoride ion-response in H_2O-MeOH (1: 4 w/w) at pH 5.5. On another front, Zn^<II>-DPA (DPA = dipicolylamine)-appended phenylboronic acid forms an assembly with alizarin-dye under neutral conditions. Addition of pyrophosphate (Ppi) causes reorganization of the complex to produce an alternative boronate ester assembly and caused an increase in fluorescence. The related bis (Zn^<II>-DPA)-appended phenylboronic acid - ARS (alizarin red S) ensemble exhibited a selective response for phytate. 2) Ion-pair driven molecular capsule Taken advantage of reversible boronate esterification we have developed the ion pair-driven heterodimeric capsule formation of a cyclotricatechylene 1 and a boronic acid-appended hexahomotrioxacalix [3] arene 2. Although 1 does not interact with 2 in a protic solution, in the presence of Et4NAcO quantitative formation of a heterodimeric capsule via boronate esterification was observed in the NMR containing ^1H, ^1H ROESY and DOSY, a direct result of anion-induced boronate ester formation and the Et_4N^+ template. Reversible boronate esterification allowed us to selectively control capsule assembly using pH switching.

  • Research Products

    (6 results)

All 2008 2007 2006 Other

All Journal Article (3 results) (of which Peer Reviewed: 2 results) Presentation (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Ion Pair-Driven Heterodimeric Capsule Based on Boronate Esterification: Construction and the Dynamic Behavior2007

    • Author(s)
      K. Kataoka, T. D. James, and Y. Kubo
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 15126-15127

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Highly Selective Ion Detection Based on a Fluorescence Alizarin-ο-aminomethylp henylboronic Acid Ensemble in Aqueous MeOH Solution2006

    • Author(s)
      Y. Kubo, T. Ishida, T. Minami, and T. D. James
    • Journal Title

      Chem. Lett. 35

      Pages: 996-997

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Highly Selective Ion Detection Based on a Fluorescence Alizarin-o-Aminomethylphenylboronic Acid Ensemble in Aqueous MeOH Solution2006

    • Author(s)
      Y. Kubo, T. Ishida, T. Minami, and T. D. James
    • Journal Title

      Chem. Lett 35

      Pages: 996-997

    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] イオンペアで誘導されるヘテロダイメックカプセルの合成とその動的挙動2007

    • Author(s)
      久保 由治
    • Organizer
      第37回構造有機化学討論会
    • Place of Presentation
      北海道大学学術交流会館
    • Year and Date
      2007-10-28
    • Description
      「研究成果報告書概要(和文)」より
  • [Remarks] 「研究成果報告書概要(和文)」より

    • URL

      http://www.apc.saitama-u.ac.jp/ygosei/

  • [Patent(Industrial Property Rights)] 特許権2008

    • Inventor(s)
      久保・野中・堀江
    • Industrial Property Rights Holder
      国立大学法人埼玉大学
    • Industrial Property Number
      特願2008-027508
    • Filing Date
      2008-02-07
    • Description
      「研究成果報告書概要(和文)」より

URL: 

Published: 2010-02-04  

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