Spectral-luminescence characteristics of 1,3-diaryl-4,7-phenanthrolines

Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives

“…All electronic absorption spectra kept still up the fine structure, specific to phenanthrene spectrum. 42 The nature of the (di-, tetra)hydropyrrole ring together with that if its substituents exerted an important influence on the position of the absorption and emission bands of phenanthroline derivatives. Thus, the presence of CN or COOMe groups in position C-3 of the pyrrole like moiety resulted in a blue shift of the absorption and emission bands of phenanthroline derivatives (4, 7).…”

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

“…The luminescence spectral characteristics of more than 100 compounds of the aza-and diazaphenanthrene series were investigated; among them there were substances (derivatives of benzo[f]quinoline, 4,7-phenanthroline) having high fluorescence quantum yields (60-80%) and promising as luminescent additives, e.g., for coloring polymeric fibers [26,[111][112][113][114][115][116][117][118][119].…”

Three component condensation of 6-quinolylamine with aromatic aldehydes and cyclohexyl 1,3-diketones

“…On the basis of previous investigations [4, 5] we proposed that the final products of the cascade of heterocyclization are the 8-aryl-7,8,9,10,11,12-hexahydrobenzo[a][4,7]phenanthrolin-11-ones A, these being formed via reaction of the 6-quinolylamine 1 with arylaldehydes with separation of the Schiff bases 5a,b, addition of a molecule of 1,3-diketone to the C=N bond of the azomethine, and the following cyclocondensation of the product B. However, on the basis of the 1 H NMR spectroscopic data (Table 1) we have shown that the reaction results selectively in the structures formed (which are isomeric with A) and these are the 12-aryl-8,9,10,12-tetrahydro-7H-benzo[b] [4,7]phenanthrolin-11-ones 4a,b. __________________________________________________________________________________________…”

“…Such reactions include the three component condensation of aromatic amines with aldehydes and CH-acids and were the basis of novel methodology developed by us for the synthesis of polycondensed nitrogen containing heterocycles of the aza-and diazaphenanthrene series [3][4][5][6], which are of promise as light sensitive materials, luminophores, and bioactive material with a broad range of action [7][8][9].…”

“…Such reactions include the three component condensation of aromatic amines with aldehydes and CH-acids and were the basis of novel methodology developed by us for the synthesis of polycondensed nitrogen containing heterocycles of the aza-and diazaphenanthrene series [3][4][5][6], which are of promise as light sensitive materials, luminophores, and bioactive material with a broad range of action [7][8][9].With the object of preparing novel 4,7-phenanthrolines we have studied in this work the condensation of 6-quinolylamine 1 with the substituted benzaldehydes 2a,b and the cyclic β-diketones 1,3-cyclohexanedione 3a and 5,5-dimethyl-1,3-cyclohexanedione (dimedone) 3b.The reactions were carried out by heating an equimolar mixture of reagents in n-butanol. Thanks to the high reactivity of the β-dicarbonyl compound its reaction with the amine and aldehyde in alcoholic medium occurs in the absence of a catalyst, the role of which is fulfilled by the proton of the dissociated enol form of the β-diketone.…”