8-Hydroxyquinoline → Azobenzene

Participants

Reaction Steps

Complex 12 was synthesized through a reaction in the ethanol solution of 8-hydroxyquinoline, o,o′-dihydroxyazobenzene (L1) and AlCl3. First, a solution of 8-hydroxyquinoline (0.05M) and piperidine (0.05M) in 100 ml ethanol was added to a solution of AlCl3.6H2O (0.5M) in 10 ml ethanol very slowly with an intensive stirring. Then, a solution of L1 (0.01M) and piperidine (0.02M) in 500 ml ethanol was introduced slowly. The mixture was stirred for about 1 hour and cooled to room temperature and kept in dark for about 10 hours. A scarlet precipitate was formed when equivalent amount water was poured into the solution. The product was collected by filtration and washed with ethanol rapidly, then dried under an infrared lamp. The obtained product power showed strong red fluorescence under an ultraviolet lamp. The materials were further purified by an improved train sublimation method. The L1 ligand was obtained by typical synthesis method of azobenzene. The molecular structure of Complex 12 was supported by high-resolution mass spectrum (MS) shown in FIG. 5 and element analysis. High-resolution MS found: 383.0845240. Calc. for C21H14O3N3Al: 383.0845062 (shown in FIG. 6); Element analysis found: C, 65.9; H, 3.89; N, 10.68, Calc. For Complex 12: C, 65.80, H, 3.66; N, 10.97.

Provenance & Evidence