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has been synthesized in which the alpha-thiophene protons and/or the beta-pyrrole protons have been replaced by Me or Br substituents.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 19 条
[1]   IDENTIFICATION OF THE 1ST STEPS OF THE ELECTROCHEMICAL POLYMERIZATION OF PYRROLES BY MEANS OF FAST POTENTIAL STEP TECHNIQUES [J].
ANDRIEUX, CP ;
AUDEBERT, P ;
HAPIOT, P ;
SAVEANT, JM .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (24) :10158-10164
[2]  
Bard A. J., 2001, ELECTROCHEMICAL METH, V2nd, P50
[3]  
CARLIN RT, IN PRESS ELECTROCHIM
[4]   STERIC EFFECTS ON THE OPTICAL AND ELECTROCHEMICAL PROPERTIES OF N-SUBSTITUTED PYRROLE THIOPHENE MONOMERS AND POLYMERS [J].
FERRARIS, JP ;
ANDRUS, RG ;
HRNCIR, DC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1318-1320
[5]   SUBSTITUTIONAL ALLOYS OF ORGANIC POLYMERIC CONDUCTORS [J].
FERRARIS, JP ;
SKILES, GD .
POLYMER, 1987, 28 (02) :179-182
[6]   OPTICAL, ELECTRICAL AND ELECTROCHEMICAL PROPERTIES OF HETEROAROMATIC COPOLYMERS [J].
FERRARIS, JP ;
HANLON, TR .
POLYMER, 1989, 30 (07) :1319-1327
[7]  
JACKSON AH, 1990, REACTIVITY 1 H PYR 1, V48, P295
[8]  
KOBAYASHI Y, 1977, TETRAHEDRON LETT, P3741
[9]  
KOOREMAN HJ, 1967, RECL TRAV CHIM PAY-B, V86, P37
[10]   POLY(THIENYLPYRROLE) - PREPARATION AND PROPERTIES [J].
NAITOH, S .
SYNTHETIC METALS, 1987, 18 (1-3) :237-240