Merocyanine-type dyes from barbituric acid derivatives.
The preparation and the solvatochromic behavior of two dyes, obtained by condensation of N,N'-dimethylbarbituric acid with dimethylaminobenzaldehyde and with 4,4'-bis(N,N-dimethylamino)benzophenone (Michler's ketone) are described. The latter dye is rather sensitive to the polarity of the medium, and in particular, to the hydrogen-bond-donor ability of protic solvents. The solvatochromism of both compounds is discussed in terms of the pi* and E(T)(30) solvent polarity scales and their differences in behavior interpreted with the aid of semiempirical calculations.
Rezende
M C
MC
Facultad de Química y Biología, Universidad de Santiago de Chile. mcaroli@lauca.usach.cl
Campodonico
P
P
Abuin
E
E
Kossanyi
J
J
D001463:Barbiturates / Q000737:chemistry*; D001577:Benzophenones / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry*; D011744:Pyrimidinones / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet / Q000379:methods
C441210:1,3-dimethyl-5-(4,4'-bis(dimethylaminophenyl)methylene)-2,4,6-(1H,3H)-pyrimidine-trione; C441212:1,3-dimethyl-5-(4-dimethylaminophenyl)-methylene-2,4,6(1H, 3H)-pyrimidinetrione; D001463:Barbiturates; D001577:Benzophenones; D005456:Fluorescent Dyes; D011743:Pyrimidines; D011744:Pyrimidinones; D012997:Solvents; C014682:Michler's ketone; C003954:merocyanine dye