Study On Synthesis And Fluorescence Properties Of Fused-Ring Aromatics Containing Phenylethynyl Groups

Fused-ring aromatics containing phenylethynyl groups have been widely applied to the field of chemistry luminescence, electroluminescence and so on because of their excelent performance derived from their special structure. Linear fused-ring aromatics with symmetrically substituted phenylethynyl groups are of great interest for their high fluorescene efficiency and low luminescence band.In this paper, 6,11-diphenyl-5,12-naphthacenequinone and 2-methyl-6,11-diphenyl- 5,12-naphthacenequinone reacted with nucleophilic reagents such as lithium phenylacetylide, lithium 4-methylphenylacetylide, lithium 4-methoxyphenylacetylide under reflux in dioxide. Then without separation, the hydrolyzed products were treated with a solution of stannous chloride in acetic acid to form 6,11 -diphenyl-5,12-phenylethynylnaphthacene,6,11 -diphenyl-5,12-p-tolylethynylnaphthacene,6,11 -diphenyl-5,12-p-(4-methoxyphenylethynyl)naphthacene,2-methyl-6,11 -diphenyl-5, 2-phenye-thynylnaphthacene,2-methyl-6,l1 -diphenyl-5,12-p-tolylethynylnaphthacene and 2-me-thyl-6,11-diphenyl-5,12-p-(4-methoxyphenylethynyl)naphthacene. Among the target products, 6,11 -diphenyl-5,12-phenylethynylnaphthacene, 6,11 -diphenyl-5,12-p- tolyl-ethynyl-naphthacene,6,11 -diphenyl-5,12-p-(4-methoxyphenylethynyl)naphthacene and 2-methyl-6,11 -diphenyl-5,12-phenylethynylnaphthacene,2-methyl-6,11 -diphenyl- 5,12 -p-tolylethynylnaphthacene,2-methyl-6,11 -diphenyl-5,12-p-(4-methoxyphenylethyny-l)naphthacene have not been reported so far.All above-mentioned procedures were monitored by HPLC and TLC. The products were characterized by MS, IR, NMR, UV and FL spectra. The relationships between their structures and ultraviolet and fluorescence performance were discussed.