树枝状1,8-萘酰亚胺化合物的合成和荧光性能

Synthesis and Fluorescence Properties of Dendritic 1,8-Naphthalimides

以三聚氯氰、无水哌嗪、N-氨乙基哌嗪、4-溴-1,8-萘酸酐为主要原料,通过收敛法高效地合成了四种具有反应活性的树枝状1,8-萘酰亚胺化合物,对产物进行了红外光谱(IR)和核磁共振(1H-NMR、13C-NMR)表征,并研究了其荧光光谱性能。结果表明,该合成工艺简单,无需繁杂的官能团保护,且每步的收率都在90%以上,污染小;得到的树状产物在常见非质子溶剂中具有很好的溶解性;当树状产物的核上连接哌嗪而形成Dπ--A结构后,最大荧光发射波长由442 nm变为512 nm,发生了明显的红移;而且随树状产物代数的增加,荧光强度几乎成倍增长。有望作为一类非常重要的功能材料,具有良好的应用前景。

Four dendritic 1,8-naphthalimides bearing reactive groups were efficiently synthesized via a convergent method,using cyanuric chloride,anhydrous piperazine,N-aminoethyl piperazine as main materials.Structures of the products were characterized by infrared spectrum（IR） and nuclear magnetic resonance spectrum（1H-NMR and 13C-NMR）,respectively,and their fluorescent performance was also researched.The results indicate that the method is easy to manipulate without tedious protection procedure,and over 90% yields are obtained in each step.The products have good solubility in most common aprotic solvents.A sharp red shift of fluorescence from 442 nm to 512 nm was observed when piperazine was coupled to the core of the dendrimer to form a D-π-A architecture; the fluorescent intensity grew almost two folds with increasing dendrimer generation.Thus,easy synthesis together with good fluorescent performance of the dendrimers would make them have promising applications in important functional materials.