Construction of non-covalent bond type n-conjugated adducts applicable as molecular wires

2007 Fiscal Year Final Research Report Summary

• Project/Area Number: 18550165
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Functional materials/Devices
• Research Institution: Shimane University
• Principal Investigator: YAMAGUCHI Isao Shimane University, Department of Material Science, Associate Professor (00272708)
• Project Period (FY): 2006 – 2007
• Keywords: π-conjugated guest molecule / cyclodextrin / donor / acceptor / π-conjugated adduct / expansion of π-conjugation system

Research Abstract

AD-π -A (D = donor and A = acceptor)type n-conjugated guest molecule (1) was synthesized by reaction of p-phenylenedimiane, 2-flufural, and 2-pyridinecaroxaldehyde in a 2:1:1 molar ratio. A π-conjugated adduct (2) was obtained from a mixture of an N,N-dimethylformamide solution of 1 with an aqueous solution of γ-cyclodextrin (γ-CD) as a precipitate. Powder X-ray diffraction, solid state ^<13>C NMR, and differential scanning calorimetry analyses suggested that the guest molecules were included in the cavity of γ-CD. Observation of absorption of 2 at a longer wavelength than that of 1 suggested that the adduct 2 has an expanded z-conjugated system. Cyclic voltammetry analysis indicated that 2 received electrochemical oxidation. The D-A interaction between the guest molecules and geometrical fitness were essential for the formation of the expanded π-conjugated system. The adducts were electrochemically active in films.

Research Products

• [Journal Article] π-Conjugated Polymers Having Diaza[12]annulene Ring and Aminopenta-2,4-dienylidene Groups Generated by Ring-opening of Pyridinium Ring (2007)
  • Author(s): I. Yamaguchi, Y. Gobara, M. Sato
  • Journal Title: J. Polym. Chem.: Part A: Polym. Chem. 45 Pages: 1507-1514
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] Polymer Possessing Diaza-18-crown 6-Ether Linked by π-Conjugated Aminopenta-2,4-dienylidene Groups Generated by Ring-opening of Pyridinium Ring (2007)
  • Author(s): I. Yamaguchi, S. Shingai, M. Sato
  • Journal Title: Polym. J. 39 Pages: 745-748
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] N-Arylated Pyridinium Salts Having Reactive Groups (2007)
  • Author(s): I. Yamaguchi, H. Higashi, S. Shigesue, S. Shingai, H. Higashi, M. Sato
  • Journal Title: Tetrahedron Lett. 48 Pages: 7778-7781
  • Description: 「研究成果報告書概要(和文)」より
  • Peer Reviewed
• [Journal Article] π-Conjugated Polymers Having Diaza[12]annulene Ring and Aminopenta-2,4- dienylidene Groups Generated by Ring-opening of Pyriclinium Ring (2007)
  • Author(s): I., Yamaguchi, Y., Gobara, M., Sato
  • Journal Title: J. Polym. Chem. : Part A : Polym. Chem 45 Pages: 1507-1514
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Polymer Possessing Diaza-18-crown 6-Ether Linked by n-Conjugated Aminopenta- 2,4-dienylidene Groups Generated by Ring-opening of Pyridinium Ring (2007)
  • Author(s): I., Yamaguchi, S., Shingai, M., Sato
  • Journal Title: Polym. J 39 Pages: 745-748
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] N-Arylated Pyridinium Salts Having Reactive Groups (2007)
  • Author(s): I., Yamaguchi, H., Higashi, S., Shigesue, S., Shingai, H., Higashi, M., Sato
  • Journal Title: Tetrahedron Lett 48 Pages: 7778-7781
  • Description: 「研究成果報告書概要(欧文)」より