菲并咪唑磺酸(羧酸)衍生物的合成与表征

Synthesis and characterization of sulfonic acid(carboxylic acid)derivatives based on phenanthroimidazole

尽管菲并咪唑衍生物具有优良的光化学性能,但其较差的水溶性在一定程度上限制了其应用范围.将磺酸(羧酸)基团引入到菲并咪唑结构,旨在设计和合成水溶性菲并咪唑衍生物.以9,10-菲醌、乙酸铵、对氨基苯磺酸(甲酸)、苯甲醛为原料,采用“一锅法”将磺酸(羧酸)基团引入到菲并咪唑结构中,合成了菲并咪唑磺酸(羧酸)衍生物.通过优化反应物的物质的量比、催化剂种类和用量、反应溶剂等因素,确定了合成菲并咪唑磺酸(羧酸)衍生物的较佳反应条件,产物收率在75%~89%.采用熔点、红外光谱、核磁氢谱和碳谱对所合成的菲并咪唑磺酸(羧酸)衍生物的结构进行表征和确认.

Although phenanthroimidazole derivatives have manifested excellent optical properties,most of their solubility in water were relatively poor which restrained their applications in the many fields.The sulfonic and carboxylic groups were functionally introduced into the moiety of phenanthroimidazole in order to design,synthesize and improve the solubility of phenanthroimidazole derivatives.Sulfonic acid and carboxylic acid derivatives based on phenanthroimidazole were synthesized by the“one-pot”reaction of 9,10-phenanthraquinone,ammonium acetate,p-aminobenzene sulfonic acid(carboxylic acid)and benzaldehyde through the introduction of sulfonic and carboxylic groups.The optimized reaction conditions were obtained by the adjustment of the quantity ratio of raw materials,the type and amount of catalyst,and solvents with the moderate yield from 75%to 89%.The structures for synthesized sulfonic acid(carboxylic acid)derivatives based on phenanthroimidazole were characterized and determined by the method of melting point,IR,1H and 13C NMR.