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J Fluoresc. 2013 May;23(3):425-37. doi: 10.1007/s10895-013-1156-3. Epub 2013 Jan 18.

N-triazinyl derivatives of 1- and 9-aminoanthracene: synthesis and photo-physical properties.

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Institute of Organic Chemistry and Technology and Institute of Polymeric Materials, Faculty of Chemical Technology, University of Pardubice, Pardubice, Czech Republic.


New N-triazinyl derivatives were synthesized by reaction of cyanuric chloride with 1- and 9-aminoanthracenes and subsequent nucleophilic substitution of chlorine atoms on triazinyl ring with methoxy and/or phenylamino groups. The compounds were characterized by (1)H and (13)C NMR and mass spectra. The influence of the chemical structure and solvent polarity on the UV/Vis absorption and fluorescence spectra and fluorescence quantum yields were investigated. Semi-empirical computations revealed highly polar CT states in singlet excited state manifold connected with charge-transfer from the hydrocarbon moiety to the triazinyl ring. The relationships between the CT-to-emitting state energy gap, solvent polarity and fluorescence quantum yield were discussed.

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