An expeditious synthesis of 6,7-dihydrodibenzo[ b , j ][4,7] phenanthroline derivatives as fluorescent materials.

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-k via Suzuki coupling, 8 by Buchwald-Hartwig amination, and 9a-b via 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 [italic small upsilon, Greek, macron] ), and quantum yield ( Φ f ) were calculated for all these compounds.