Article
  • Synthesis and Application of Oligo(3-Methylthiothiophene) Using Palladium Catalyst
  • Park SH, Jung MY, Bae JY
  • Palladium 촉매를 이용한 Oligo(3-methylthiothiophene)의 합성과 응용
  • 박상호, 정문영, 배진영
Abstract
In this study, oligo(3-methylthiothiophene) was synthesized from thiophene derivative according to the method of reductive coupling using palladium catalyst. For the preparation of monomer, 3-methylthiothiophene was first synthesized through the metal-halogen exchange reaction of 3-bromothiophene with n-butyllithium, and the corresponding 2,5-dibromo-3-methylthiothiophene was formed by bromination. Their synthesis and characterization were determined by 1H-NMR and ATR analyses. Thermal stability of the oligothiophene was monitored by thermogravimetric analysis (TGA). Thermal evaporation of the oligo(3-methylthiothiophene) on the substrate was attempted for OTFT applications.

본 연구에서는 OTFT의 유기물 반도체 층으로 쓰일 수 있는 oligo(3-methylthiothiophene)를 전이금속 촉매인 palladium 촉매를 이용한 커플링 중합법을 이용하여 합성하였다. Thiophene 올리고머의 단량체를 합성하기 위해서 metal halogen exchange reaction에 의하여 3-methylthiothiophene를 합성하였고, thiophene 구조의 2, 5번의 위치에 brome기를 도입함으로써 최종적으로 2,5-dibromo-3-methylthiothiophene를 합성하였다. 합성된 단량체와 올리고머는 1H-NMR, ATR 분석을 통하여 그 구조를 확인하였으며, TGA로 열적 안정성을 관찰하였고 진공 증착법(thermal evaporation)을 이용하여 기판상에 증착시켜 OTFT 소재로서의 적용 가능성을 확인하였다.

Keywords: OTFT; thiophene; palladium; coupling

References
  • 1. MacDiarmid AG, Chiang CK, Findher CR, Park YW, Heeger AJ, Shirakawa H, Louis EJ, Gau SC, Phys. Rev. Lett., 39, 1098 (1977)
  •  
  • 2. Kudo K, Yamashina M, Moriizumi T, Jpn. J. Appl. Phys., 23, 130 (1984)
  •  
  • 3. Ebisawa F, Kurokawa T, Nara S, J. Appl. Phys., 54, 2355 (1983)
  •  
  • 4. Tsumura A, Koezuka H, Ando T, Appl. Phys. Lett., 49, 1210 (1986)
  •  
  • 5. Tsumura A, Koezuka H, Ando T, Synth. Met., 18, 699 (1987)
  •  
  • 6. Paloheimo J, Stubb H, Yli-Lahti P, Kuivalainen P, Synth. Met., 41, 563 (1991)
  •  
  • 7. Bao Z, Dodabalapur A, Lovinger AJ, Appl. Phys. Lett., 69, 4108 (1996)
  •  
  • 8. Wu XM, Chen TA, Rieke RD, Macromolecules, 29(24), 7671 (1996)
  •  
  • 9. Wu X, Chen TA, Zhu L, Rieke RD, Tetrahedron Lett., 35, 3673 (1994)
  •  
  • 10. Taylor EC, Vogel DE, J. Org. Chem., 50, 1002 (1985)
  •  
  • 11. Wu XM, Chen TA, Rieke RD, Macromolecules, 28(6), 2101 (1995)
  •  
  • 12. Lee TS, Kim J, Bae JY, Polymer, 45(15), 5065 (2004)
  •  
  • 13. Milton OMaterials Science of Thin Films, 2nd edition, Academic Press, San Diego, California, ch. 7 (2001)
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2023 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2007; 31(6): 469-473

    Published online Nov 25, 2007

  • Received on May 31, 2007
  • Accepted on Aug 29, 2007