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本文采用对位含有吸电子和供电子基团的醛为原料,通过与N-烷基-m-氨基酚进行酸催化缩合后得到目标产物。利用醛代替酸酐进行缩合,避免了传统酸酐熔化缩合后副产物较多,反应后处理困难的缺点。同时该合成方法还避免了5和6位异构体的产生,获得单一的产物,从而大大提高了产率。通过对两种不同化合物的合成方法研究和光谱性能测试后发现,当醛的对位是吸电性基团硝基时,合成向有利于高收率的方向进行,相反,当醛的对位是供电子基团N,N-二甲氨基时,反应对染料收率的提高不利。同时,对位是硝基时,染料的荧光量子产率和光稳定性也降低;而对位是N,N-二甲氨基时,其荧光量子产率和光稳定性也较好。这可能是由于取代基推拉电子的不同性质调节了染料核心结构的电子云密度,从而改变了染料的光谱性能。
In this paper, an aldehyde containing electron-withdrawing and donating groups is used as a starting material to obtain the target product by acid-catalyzed condensation with N-alkyl-m-aminophenol. The use of aldehydes instead of anhydride for condensation, to avoid the traditional acid anhydride after melting more by-products, the reaction after the treatment of the shortcomings. At the same time, the synthesis method also avoids the production of 5 and 6 isomers to obtain a single product, thus greatly improving the yield. Through the synthesis of two different compounds and spectroscopic properties of the test showed that when the para-position of the aldehyde is the electron-accepting group nitro, the synthesis is conducive to the high yield of the direction, on the contrary, when the para Is an electron donating group N, N-dimethylamino, the reaction adversely affects the increase of the dye yield. At the same time, when the para-position is a nitro group, the fluorescence quantum yield and light stability of the dye are also decreased. When the para-position is N, N-dimethylamino, the fluorescence quantum yield and light stability are also good. This may be due to the different nature of the substituent push-pull electrons regulate the electronic cloud density of the dye core structure, thus changing the spectral properties of the dye.