A rapid and efficient method has been developed for the synthesis of 13,14-dimethyl-6,7-dihydrodibenzo[,][4,7]phenanthroline derivatives (3a-d) through the Friedländer condensation of 2-aminoarylketone with 1,4-cyclohexanedione under solvent-free conditions using -toluenesulphonic acid. The synthetic utility of compounds 3a, 3b, and 3c was demonstrated by synthesizing compounds 6a-k Suzuki coupling, 8 by Buchwald-Hartwig amination, and 9a-b NBS bromination. Significantly, the emission band corresponding to the π-π* electronic transition of compounds 3a, 6a, 6d, 6f, and 8 showed a redshift with increasing polarity of the solvents. Molar extinction coefficient (), Stoke's shift (Δ), and quantum yield ( ) were calculated for all these compounds.
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| http://dx.doi.org/10.1039/d2ra05198b | DOI Listing |
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