A MECHANISTIC STUDY OF THE ELECTROCHEMICAL OXIDATION OF 2,5-BIS(2-THIENYL)PYRROLES

被引:64
|
作者
NIZIURSKIMANN, RE [1 ]
SCORDILISKELLEY, C [1 ]
LIU, TL [1 ]
CAVA, MP [1 ]
CARLIN, RT [1 ]
机构
[1] UNIV ALABAMA,DEPT CHEM,BOX 870336,TUSCALOOSA,AL 35487
关键词
D O I
10.1021/ja00056a011
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of 2,5-bis(2-thienyl)pyrroles has been synthesized in which the alpha-thiophene protons and/or the beta-pyrrole protons have been replaced by Me or Br substituents. A systematic electrochemical investigation of these compounds has yielded rate constants of 36 000 M-1 s-1 for linear coupling of the electrochemically generated cation radicals and 14 000-17 000 M-1 s-1 for branched coupling reactions of the cation radicals. These results constitute the first kinetic evidence for appreciable branched coupling of the electrochemical radical cations of an oligomer precursor of a conducting polymer.
引用
收藏
页码:887 / 891
页数:5
相关论文
共 50 条
  • [21] Precise sequence control in linear and cyclic copolymers of 2,5-bis(2-thienyl)pyrrole and aniline by DNA-programmed assembly
    Schuster, Gary B.
    Chen, Wen
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [22] ELECTROCHEMICAL OXIDATION OF 2,5-DI-(-2-THIENYL)-PYRROLE IN ACETONITRILE - CATHODIC STRIPPING OF THE ELECTROGENERATED CONDUCTING POLYMER
    OTERO, TF
    CARRASCO, J
    FIGUERAS, A
    BRILLAS, E
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1994, 370 (1-2) : 231 - 239
  • [23] Pyrrolyl-, 2-(2-thienyl)pyrrolyl- and 2,5-bis(2-thienyl)pyrrolyl-nucleosides: synthesis, molecular and electronic structure, and redox behaviour of C5-thymidine derivatives
    Galindo, Miguel A.
    Hannant, Jennifer
    Harrington, Ross W.
    Clegg, William
    Horrocks, Benjamin R.
    Pike, Andrew R.
    Houlton, Andrew
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (05) : 1555 - 1564
  • [24] Mechanistic Insights into the Aerobic Oxidation of 2,5-Bis(hydroxymethyl)furfural to 2,5-Furandicarboxylic Acid on Pd Catalysts
    Yang, Jie
    Huai, Liyuan
    Chen, Chunlin
    Zhang, Jian
    ACS APPLIED MATERIALS & INTERFACES, 2025, 17 (06) : 10168 - 10178
  • [25] Synthesis of 2,5-bis(phosphinoylmethyl)- and 2,5-bis(thiophosphinoylmethyl)-thiophenes
    Camus, Jean-Michel
    Pailloux, Sylvie
    Shirima, Cornel Edicome
    Paine, Robert T.
    MAIN GROUP CHEMISTRY, 2011, 10 (01) : 25 - 36
  • [26] Easy formation of gold-like lustrous crystals with a high melting point from 1-aryl-2,5-bis[5-(tricyanoethenyl)-2-thienyl]pyrroles
    Ogura, K
    Zhao, R
    Jiang, MT
    Akazome, M
    Matsumoto, S
    Yamaguchi, K
    TETRAHEDRON LETTERS, 2003, 44 (18) : 3595 - 3598
  • [27] Chloromethylation of Bis(2-thienyl) Sulfide
    L. K. Papernaya
    E. N. Sukhomazova
    E. P. Levanova
    G. F. Myachina
    E. N. Deryagina
    Russian Journal of Organic Chemistry, 2002, 38 : 1495 - 1497
  • [28] Chloromethylation of bis(2-thienyl) sulfide
    Papernaya, LK
    Sukhomazova, EN
    Levanova, EP
    Myachina, GF
    Deryagina, EN
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (10) : 1495 - 1497
  • [29] SYNTHESIS, ELECTROCHEMICAL POLYMERIZATION AND PROPERTIES OF POLY(2,5-DI-(2-THIENYL)-PYRROLE)
    MCLEOD, GG
    MAHBOUBIANJONES, MGB
    PETHRICK, RA
    WATSON, SD
    POLYMER, 1986, 27 (03) : 455 - 458
  • [30] SYNTHESIS, ELECTROCHEMICAL POLYMERIZATION AND PROPERTIES OF POLY(2,5-di-(-2-THIENYL)-PYRROLE).
    McLeod, Gordon G.
    Mahboubian-Jones, M.G.B.
    Pethrick, Richard A.
    Watson, Steven D.
    Truong, D.
    Galin, J.C.
    Francois, J.
    Polymer, 1986, 27 (03): : 455 - 458