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2002 Fiscal Year Final Research Report Summary

Design and estimation of fluorescent chiral sensor : from uni-molecular system to organized approach

Research Project

Project/Area Number 13650911
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KUBO Yuji  Saitama University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (80186444)

Project Period (FY) 2001 – 2002
Keywordsfluorescent sensor / isothiouronium group / anion recognition / organized molecular layer / chirality / chilality memory / porphyrin / crown ether
Research Abstract

Synthesis of optical sensors being capable of recognizing and reading out the shape of analyte precisely is one of scientific challenge in the area of molecular recognition chemistry. Most notably, chiral sensing would be desirable not only in analytical chemistry but also in pharmacology. In this project, our strategy to develop elaborated sensing systems is based on the anion recognition. A family of isothiuronium salts, which are known as synthetic intermediates for the conversion of alkyl halides to the corresponding thiols, has potential as one of key functional groups toward this end. Indeed, a sophisticated combination of the functional entity and suitable fluorophore could allow production of a new type of chemosensors via regulation of the efficiency of the photoinduced electron transfer process. In 2002, we tried to develop an isothiouronium derived uni-molecular system for chiral recognition as well as an organized molecular layer. In the latter case, by use of newly synthesized amphiphilic isothiouronium compounds, we successfully prepared the corresponding organized molecular films. Now the detailed molecular recognition phenomena at air-water interface are under investigation.
Alternative approach is to develop a novel achiral-to-chiral transformation at the molecular level using "dynamic" host-guest interaction. In this context, chirality-transfer control has been successfully achieved using a 2,2'-biphenyl- 20-crown-6-bridged bis(zinc(II) porphysic). Further, chirality-induction in a large-sized crown ether with a highly conformational flexibility was obtained through K^+ and I coordinated self-assembly in the solid state. Taken together, I believe that these findings would open new way to "dynamic" chiral recognition.

  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] 入保 由治: "ホスト・ゲスト相互作用に基づく光機能性分子システムの新展開"オレオサイエンス. 1. 617-625 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Kubo, T.Ohno, J.Yamanaka, S.Tokita, T.Iida, Y.Ishimaru: "Chirality-Transfer Control Using a Heterotopic Zinc(II) Porphyrin Dimer"Journal of the American Chemical Society. 123. 12700-12701 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Tozawa, S.Tokita, Y.Kubo: "An Allosteric Crown Ether-Induced Activity Control for the Cleavage of a Phophodiesrter Bond"Tetrahedron Letters. 43. 3455-3457 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Kubo, S.Ishihara, M.Tsukahara, S.Tokita: "Isothiouronium-Derived Simple Fluorescent Chermosensors of Anions"Journal of the Chemical Society, Perkin Transactions 2. 1455-1460 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Tozawa, T.Tachikawa, S.Tokita, Y.Kubo: "Chirality Induction in a Dibenzo-30-Crown-10 Congener Promoted by an Ion-Pair Coordinated Self-Assembly"New Journal of Chemistry. 27. 221-223 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Kubo: "New Development of Photo-Functional Molecular Systems Based on Host-Guest Interaction"Oleoscience. 1. 617-625 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Kubo, T. Ohno, J. Yamanaka, S. Tokita, T. lida, and Y. Ishimaru: "Chirality-Transfer Control Using a Heterotopic Zinc(II) Porphyrin Dimer"Journal of the American Chemical Society. 123. 12700-12701 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tozawa, S. Tokita, and Y. Kubo: "An Allosteric Crown Ether-Induced Activity Control for the Cleavage of a Phosphodiester Bond"Tetrahedron Letters. 43. 3455-3457 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Kubo, S. Ishihara, M. Tsukahara, and S. Tokita: "Isothiouronium-Derived Simple Fluorescent Chemosensors of Anions"Journal of the Chemical Society, Perkin Transactions. 2. 1455-1460 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tozawa, T. Tachikawa, S. Tokita, and Y. Kubo: "Chirality Induction in a Dibenzo-30-Crown-10 Congener Promoted by an Ion-Pair Coordinated Self-Assembly"New Journal of Chemistry. 27. 221-223 (2003)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2004-04-14  

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