新型5-[10-(9-羧基蒽基)]-间苯二甲酸的合成及荧光性质

Synthesis and Luminescent Properties of A New5-(10-(9-Carboxyanthracenyl) ) isophthalic Acid

以5-氨基-间苯二甲酸二甲酯为原料,经重氮化溴取代、Miyaura硼酸酯化反应生成3,5-二甲氧羰基苯硼酸频哪醇酯(3)。此外,以9-蒽甲酸为原料,经溴化、酯化反应生成10-溴-9-蒽甲酸甲酯(6)。最后以化合物3和6为原料,经Suzuki偶联、水解反应得到目标化合物5-[10-(9-羧基蒽基)]-间苯二甲酸。其结构经1H NMR、13C NMR和高分辨质谱表征。研究结果表明,该化合物钠盐水溶液具有发蓝光的性质,最大发射波长为425nm,同时也有较好的荧光量子效率。

5-（ 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl） isophthalic acid dimethyl ester（ 3） was synthesized from 5-amino-isophthalic acid dimethyl ester by diazotization,bromination and Miyaura boration. Moreover,methyl10-bromo-anthracene-9-carboxylate（ 6） was synthesized from anthracene-9-carboxylic acid by bromination and esterification. Finally,a new 5-（ 10-（ 9-carboxyanthracenyl））-isophthalic acid（ 8） was synthesized from compound 3and 6 via Suzuki coupling and hydrolytic reaction. The structure was characterized by1 H NMR,13 C NMR and HRMS. The fluorescent experiments showed that the emission maxima of compound 8 in the aqueous solution is at425 nm,and it possesses blue fluorescent property and good fluorescence quantum efficiency.