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Issue 3, 2012
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Probing the surface polarity of inorganic oxides using merocyanine-type dyes derived from barbituric acid

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Abstract

The solid state complexes, solvatochromic and acidochromic behaviour of four merocyanine-type dyes derived from barbituric and thiobarbituric acid and their use as solvatochromic probe molecules for coloured surfaces are described. The dyes were obtained by condensation reaction of barbituric, N-methylbarbituric, N,N′-dimethylbarbituric and thiobarbituric acid with 4-N,N-dimethylaminocinnamaldehyde. The dyes were characterised by means of liquid and solid state NMR techniques (1H MAS NMR, 1H–1H DQ MAS NMR, 13C CPMAS NMR), single-crystal X-ray analysis, UV/vis and IR measurements. The solvatochromism has been investigated in 43 solvents and interpreted in terms of Kamlet–Taft parameters α, β, and π*. Altogether, the solvatochromic properties of these four dyes were determined mainly by the hydrogen bond donating (HBD) ability and the polarisability/dipolarity of a solvent. The interactions of the dyes with oxidic and metal surfaces were studied. Their perichromic behaviour was compared with that of established solvatochromic dyes for the determination of α, β, and π*, namely dicyano-bis-(1,10-phenanthroline)-iron(II)-complex (1), 3-(4-amino-3-methylphenyl)-7-phenyl-benzo-[1,2-b:4,5-b′]-difuran-2,6-dione (2) and 4-tert-butyl-2-(dicyanomethylene)-5-[4-(diethylamino)benzylidene]-Δ3-thiazoline (3). The barbituric acid dyes were used to probe the surface polarity of coloured oxides like tungsten(VI) oxide and iron(III) oxide. The interactions between the dyes and metals like zinc and aluminium were also investigated.

Graphical abstract: Probing the surface polarity of inorganic oxides using merocyanine-type dyes derived from barbituric acid

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Publication details

The article was received on 28 Sep 2011, accepted on 23 Nov 2011 and first published on 12 Dec 2011


Article type: Paper
DOI: 10.1039/C2NJ20835K
Citation: New J. Chem., 2012,36, 674-684
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    Probing the surface polarity of inorganic oxides using merocyanine-type dyes derived from barbituric acid

    S. Seifert, A. Seifert, G. Brunklaus, K. Hofmann, T. Rüffer, H. Lang and S. Spange, New J. Chem., 2012, 36, 674
    DOI: 10.1039/C2NJ20835K

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