Abstract
A direct synthesis of previously unknown 2-[5-(4-hydroxyphenyl)-2-oxo-4-phenyl-1,2-dihydro-3H-pyrrol-3-ylidene]malononitriles was carried out, which are donor–acceptor chromophores bearing phenol moiety as an electron-donor fragment. A developed synthetic route was based on the initial reaction of methoxy-substituted aryl ketones with tetracyanoethylene and resulted in 4-(4-methoxyphenyl)-4-oxo-3-butane-1,1,2,2-tetracarbonitriles, which were further converted into corresponding 2-[5-(4-methoxyphenyl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene]malononitriles by the action of morpholine. Treatment of the latter with boron tribromide led to demethylation of the methoxy group and formation of the desired phenolic chromophores. The obtained phenol derivatives are intensely colored compounds found to be capable to reversible high-contrast phenol-phenolate (quinoid) transformation. Their solvatochromic behavior was directly related to the donor number (DN) of the solvent and well fitted to the Kamlet-Taft model.
Published Version
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