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2‐Arylazo‐1‐vinylpyrroles: A Novel Promising Family of Reactive Dyes
Author(s) -
Trofimov Boris A.,
Schmidt Elena Yu.,
Mikhaleva Al’bina I.,
Vasil’tsov Alexander M.,
Zaitsev Alexey B.,
Smolyanitalia S.,
Senotrusova Elena Yu.,
Afonin Andrey V.,
Ushakov Igor’ A.,
Petrushenko Konstantin B.,
Kazheva Olga N.,
Dyachenko Oleg A.,
Smirnov Vladimir V.,
Schmidt Alexander F.,
Markova Marina V.,
Morozova Ludmila V.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600357
Subject(s) - chemistry , substituent , photochemistry , chromophore , protonation , copolymer , quantum yield , heck reaction , polymer chemistry , pyrrole , catalysis , transition metal , alkene , organic chemistry , palladium , fluorescence , ion , physics , quantum mechanics , polymer
New reactive dyes, 2‐arylazo‐1‐vinylpyrroles, have been synthesized in 52–94 % yield by a modified azo coupling of readily accessible 1‐vinylpyrroles with arenediazonium hydrocarbonates in aqueous ethanol (≈3:1) at 0 °C. The λ max values for the UV/Vis absorption of the dyes ranges from 377.8–480.6 nm with log ϵ = 4.11–4.99, and this strongly depends on the substituent structure both in the pyrrole and the benzene ring, and is indicative of highly polarizable and tunable chromophores. X‐ray, 1 H NMR spectroscopic and quantum chemical studies [B3LYP/6‐311 (d,p)] show the E , anti , anti isomer of the dyes to be the most stable under normal conditions. The dyes are reversibly protonated and complex to BF 3 with a color change. Their copolymerization across the vinyl group affords intrinsically colored copolymers. They have also been shown to act as good ligands in the Pd‐catalyzed Heck alkene arylation. Thus, the properties of the novel dyes are promising for creating new molecular switches, memory and recording devices, acid‐base and metal sensors, as well as transition‐metal complex catalysts.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)