2-Arylazo-1-vinylpyrroles: oligomerization in the presence of protic and aprotic acids

被引：1
|
作者：
Markova, M. V. [1 ]
Shmidt, E. Yu. [1 ]
Morozova, L. V. [1 ]
Tatarinova, I. V. [1 ]
Prozorova, G. F. [1 ]
Mikhaleva, A. I. [1 ]
Trofimov, B. A. [1 ]
机构：
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2012年 / 48卷 / 02期
基金：
俄罗斯基础研究基金会;
关键词：
aprotic and protic acids; 2-arylazo-1-vinylpyrroles; electroconductive oligomers; RADICAL POLYMERIZATION; BF2-AZOPYRROLE COMPLEX; DYES;
D O I：
10.1007/s10593-012-0987-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Arylazo-1-vinylpyrroles react with protic (CF3COOH, HCl) and aprotic (BF3) acids forming deeply colored oligomeric products consisting of soluble (in benzene, chloroform) and insoluble fractions with yields amounting to 73 %. According to the data from H-1 NMR and IR spectroscopy oligomerization takes place mainly at the 1-vinyl group with partial involvement of the pyrrole ring. The process is accompanied by capture of the catalyzing acids by the azo group, leading to strong polarization of the elementary unit with transfer of positive charge to the pyrrole ring, which thus becomes capable of further transformations with cross-linking of oligomeric chains. The obtained oligomers possess electric conductivity of 10(-13)-10(-9) S/cm, which is increased to 4.8a (TM) 10(-6) S/cm when the products are iodinated with iodine vapor.
引用
收藏
页码：280 / 286
页数：7
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