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以5-氯邻氨基苯甲酸和对甲氧基苯磺酰氯为原料缩合合成含有分子内氢键的6-氯-2-[5-氯-2-(4-对甲氧基苯磺酰胺基)]苯基-4-苯并噁嗪酮。利用BF3·OEt2氟硼化反应及与邻苯二胺的缩合反应分别制得苯并噁嗪酮的衍生物。利用红外、质谱、核磁(1HNMR、11BNMR、19FNMR)及元素分析等对化合物结构进行了表征,并研究了化合物的光学性能,热稳定性及光稳定性。研究表明,两种衍生化合物均具备超过150 nm的大斯托克斯位移,强荧光发射能力,高荧光量子产率,并且光稳定性明显优于罗丹明6G染料,分解温度甚至达到260℃以上,说明所得化合物是性能良好的光致发光材料。
Synthesis of 6-Chloro-2- [5-chloro-2- (4-p-methoxybenzenesulfonamido) -4-methoxybenzenesulfonamide with intramolecular hydrogen bond by condensation of 5-chloroanthranilic acid and p- )] Phenyl-4-benzoxazinone. Derivatives of benzoxazinone were prepared by the BF3 · OEt2 fluoroboronation reaction and the condensation with o-phenylenediamine, respectively. The structures of the compounds were characterized by IR, MS, 1HNMR, 11BNMR and elemental analysis. The optical properties, thermal stability and photostability of the compounds were also studied. The results show that both derivatives have large Stokes shift exceeding 150 nm, strong fluorescence emission ability and high fluorescence quantum yield, and their light stability is obviously better than rhodamine 6G dye, and the decomposition temperature is even above 260 ℃ , Indicating that the resulting compound is a good performance photoluminescent material.