Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore-632014 Tamil Nadu India,
Abstract:
A rapid and efficient method has been developed for the synthesis of 13,14-dimethyl-6,7-dihydrodibenzo[b,j][4,7]phenanthroline derivatives (3a–d) through the Friedländer condensation of 2-aminoarylketone with 1,4-cyclohexanedione under solvent-free conditions using p-toluenesulphonic acid. The synthetic utility of compounds 3a, 3b, and 3c was demonstrated by synthesizing compounds 6a–kvia Suzuki coupling, 8 by Buchwald–Hartwig amination, and 9a–bvia 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 (ε), Stoke''s shift (Δ), and quantum yield (Φf) were calculated for all these compounds.A rapid method has been developed for the synthesis of 13,14-dimethyl-6,7-dihydrodibenzo[b,j][4,7]phenanthroline derivatives (3a–d) through the Friedländer condensation of 2-aminoarylketone with 1,4-cyclohexanedione under neat conditions using p-TSA.