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Development of Functional Materials Based on Ene-Yne Oligomers

Research Project

Project/Area Number 07640723
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

ASO Yoshio  Hiroshima University Engineering, Associate Professor, 工学部, 助教授 (60151065)

Co-Investigator(Kenkyū-buntansha) TAKIMIYA Kazuo  Hiroshima University, Engineering, Research Associate, 工学部, 助手 (40263735)
OTSUBO Tetsuo  Hiroshima University Engineering, Professor, 工学部, 教授 (80029884)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1996: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1995: ¥1,800,000 (Direct Cost: ¥1,800,000)
KeywordsEne-yne conjugated oligomer / Functional material / Cyclopentenylene-ethynylene / Thienylene-ethynylene / pi-Electron conjugation / Helical structure / multi-cyclization reaction
Research Abstract

We have successfully synthesized 1,2-cyclopentenylene-ethynylene and 3,4-thienylene-ethynylene oligomers. The well-documented palladium-caralyzed coupling reaction of terminal alkynes and alkenyl or aryl halides was repeatedly applied to the synthesis of these oligomers, which were fully characterized by spectroscopic and elemental analyzes. Electronic absorption spectra of 1,2-cyclopentenylene-ethynylene oligomers showed bathochromic shifts with increasing chain length, indicating increasing conjugation of the pi-electrons. On the other hand, electronic spectra of 3,4-thienylene-ethynylene oligomers showed a characteristic pi-pi^<**> transition with almost identical absorption maximum, suggesting a favorable twist conformation of the thienyl-ethynyl moieties, which decreases conjugation of the pi-electrons. The solid-state conformations of 3,4-thienylene-ethynylene oligomers were elucidated by an X-ray crystallographic analysis, and they take a totally heilcal conformation. A detailed comparison of the ^1H NMR spectra of the oligomers revealed high-field shifts of the thienyl protons, supporting that the helical conformation with intramolecular stacking of the thiophene moieties also dominates in solution. A tandem cyclization reaction of the 1,2-cyclopentenylene-ethynylene system was induced at above 200゚C in a solution. Although the 3,4-thienylene-ethynylene systems were thermally stable, they were cyclized under the influence of tellurium tetrachloride to afford novel thiophene-fused pentalene system. These oligomers showed intense fluorescence in a visible region, suggesting potential materials as optoelectronic devices.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] Yoshio Aso: "3,4-Thienylene-ethynylene Oligomers" Phosphorus,Sulfur,and Silicon & the Related Elements. 72(印刷中). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] YOSHIO ASO: "3,4-Thienylene-ethynylene Oligomers" Phosphorus, Sulfur, and Silicon & the Related Elements. 72(in press). (1977)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yoshio Aso: "3,4-Thienylene-ethynylene Oligomers" Phosphorus, Sulfur, and Silicon & the Related Elements. 72(発表予定). (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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