含蒽环查尔酮衍生物的合成、晶体结构及光学性质

摘要

In this paper,four 2'-hydroxychalcone derivatives were synthesized from the reactions of 9-anthracene aldehyde with four hydroxy-acetophenones (2-hydroxyacetophenone,4-methoxy-2-hydroxyacetophenone,4-fluoro-2-hydroxy-acetophenone and 4-chloro-(4-dimethylamino)-2-hydroxychalcone) with the assistance of ultrasonic waves.The yields of the target products were 63％-75％.Characterization of the products by 1H-NMR,IR,ESI-MS and UV-VIS confirmed their structures.The four compounds all exhibit orange color in white-light and emit weak fluorescence in a 365 nm UV lamp.They show an absorption in the range of 350 nm to 426 nm in the UV-VIS spectroscopy and emit fluorescence in 450-500 nm regions.Single crystals of these compounds were obtained by slow solvent-evaporation method.Analysis of their crystal structure indicates that the four compounds belong to monoclinic crystallographic system.The angle between the anthracene ring plane and the double bond plane of chalcone is about 51.63-73.15°.Distortion of the molecular plane leads to the weak fluorescence emission of these chalcones.Among these four chalcone compounds,the luminescence of A3 is relative strong due to its J-like aggregate of molecular packing.%本文以9-蒽醛和2-羟基苯乙酮、4-甲氧基-2-羟基苯乙酮、4-氟-2-羟基苯乙酮及4-氯-2-羟基苯乙酮为原料,超声辅助合成了4种含蒽环的2'-羟基查尔酮衍生物,其产率在63％ ～ 75％.目标产物经1HNMR,IR,ESI-MS和UV-Vis表征,确认了分子结构.4种化合物在白光下呈现橘红色,在365 nm的紫外灯下荧光较弱,紫外可见吸收光谱在350 ～426 nm有吸收,荧光发射集中在450～500 nm.通过溶剂挥发法得到了4个化合物的大块单晶,晶体解析发现,4个化合物都属于单斜晶系,蒽环与查尔酮双键所在平面的二面角介于51.63°-73.15°之间,分子平面的扭曲导致了4种分子荧光发射较弱,其中荧光相对较强的化合物A3具有类J-型聚集体的分子排列.