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The Solvatofluorochromism of 2,4,6-Triarylpyrimidine Derivatives
José Rodríguez-Aguilar1, Matías Vidal1, Camila Pastenes1
1Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago, Chile.
Abstract:
Seven new 2,4,6-triarylpyrimidines were synthesized and their solvatofluorochromism investigated in 12 solvents and in an aqueous micellar solution of reduced Triton X-100. A multiparametric analysis of their emission band showed that the solvent dipolarity and basicity were mainly responsible for their solvatofluorochromism, which arose from an internal charge-transfer from a donor fragment to the pyrimidine acceptor, confirmed by theoretical calculations. In the micellar system, quenching of their fluorescence by addition of derivatives of 2,2,6,6-tetramethylpiperidinoxyl (TEMPO) radical was investigated and the results were consistent with the spectral changes brought about by the micro-heterogeneous system.
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