Collect. Czech. Chem. Commun. 2007, 72, 1255-1268

Synthesis, Oxidation and Photophysical Properties of Novel Derivatives of Acyclic Aromatic Amines

Csaba Kósaa, Jaroslav Mosnáčeka,*, Adela Bílešováa, Peter Kasákb,a, Juraj Kroneka, Martin Dankoa and Jozef Kollára

a Polymer Institute, Slovak Academy of Sciences, Dúbravska cesta 9, 842 36 Bratislava, Slovak Republic
b Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovak Republic


Conjugated acyclic arylamine derivatives, N-(4-methylphenyl)-N-(2-methyl-1-phenylpropyl)amine and N-(4-methoxyphenyl)-N-(2-methyl-1-phenylpropyl)amine, have been synthesized and characterized. Their photophysical properties have been investigated in polar methanol and non-polar cyclohexane solutions, and in PS and PMMA polymer matrices. The influence of the environment polarity as well as of the substituent in para-position of the aryl on the absorption, emission spectra and the fluorescence quantum yield has been studied. In the absorption and emission spectra, the observed absorption and emission band maxima were red shifted and the observed quantum yield was higher in the polar solution in comparison with the non-polar solution or polymer matrices. The distance of short- and long-wavelength absorption maxima in the methoxy derivative was larger and the emission band was red shifted in comparison with the methyl derivative. Chemical and photochemical oxidation of the prepared amines gives unstable nitroxides. High intramolecular quenching was observed in polymer matrix after photochemical oxidation of the amines.

Keywords: Amines; Nitroxides; Oxidations; Photochemistry; Fluorescence spectroscopy.

References: 22 live references.