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N-Triazinyl Derivatives of 1- and 9-aminoanthracene: Synthesis and Photo-Physical Properties |
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| Authors: | Hana P?ichystalová Numan Almonasy Milo? Nepra? Filip Bure? Miroslav Dvo?ák Martin Michl Ji?i ?ermák Ladislav Burgert |
| Institution: | 1. Institute of Organic Chemistry and Technology and Institute of Polymeric Materials, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, CZ-532 10, Czech Republic 2. Department of Physical Electronics, Faculty of Nuclear Sciences and Physical Engineering, Czech Technical University in Prague, v Hole?ovi?kách 2, Prague, CZ-180 00, Czech Republic 3. Research Institute for Organic Syntheses, Rybitví 296, Pardubice, CZ-533 54, Czech Republic |
| Abstract: | 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 1H and 13C 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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