Carbazole - Synthesis And Characterization Of Phenanthroline Derivatives

In this paper, six kinds of symmetry2-(4-(N-alkylcarbazoleyl))imidazo[4,5-f]phenanthroline and six kinds of asymmetry2-(9-alkyl-3-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)-9H-carbazol-6-yl)-1H-imidazo[4,5-f][1,10] phenanthroline (alkyl: ethyl,n-butyl, n-pentyl, n-hexyl, n-octyl and benzyl) have been synthesized by the cyclizationreaction with formacyl-carbazole (N-alkylation and formylation from carbazole) and1,10-phenanthroline-5,6-dione (ketonization from phenanthroline). Except the asymmetryderivative substituent by ethyl and symmetry derivative substituent by n-butyl, the others werenew derivatives. Their structures were characterized by CHN, IR,1H NMR and MS.At the same time, the reaction conditions of alkylation of carbazole have beenresearched. And the reaction mechanism and reaction condition of formylation ofcarbazole have been discussed. The ketonization of1,10-phenanthroline, including theform mechanism of impurities, the ratio of materials, reaction time, temperature etc. havebeen studied; finally, we determined the optimal condition.The electronic absorption spectrum, fluorescence spectrum, fluorescence lifetime andfluorescence quantum yield have been measured. Optimize six phenanthroline derivatives’molecular structure by using Gaussian03packets，and calculate the energy gap of frontierorbital energy level for transition. The mentioned properties and rules of effect of themolecular structure and solvent on phenanthroline derivatives have analyzed, and thenonlinear optical properties of phenanthroline derivatives n-Bu-C2, Bn-C2are studied byZ-scan technique, and the third order nonlinear optical parameters are calculated.