Chen Meihui, Cao Fengying, Huang Shizhou, Li Yangping, Zhong Min, Zhu Mingguang
College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang, 641100, People's Republic of China.
J Fluoresc. 2022 Jul;32(4):1457-1469. doi: 10.1007/s10895-022-02948-9. Epub 2022 Apr 22.
Here, three Schiff bases 3a-c, differing by the substitutions (-H, -Cl, and -N(CH)) on the phenyl ring, have been designed and synthesized via the reaction of ortho-aminophenol with benzaldehyde, 2,4-dichlorobenzaldehyde and para-dimethylamine benzaldehyde in 1:1 molar ratio with favourable yields of 89-92%, respectively. Their structural characterizations were studied by FT-IR, NMR, MALDI-MS and elemental analysis. The fluorescence behaviours of compounds 3a and 3b exhibited a severe aggregation caused quenching (ACQ) effect in EtOH/water system. On the contrary, compound 3c had an obvious J-aggregation induced emission (AIE) feature in EtOH/water mixture (v/v = 1:1), and exhibited excellent sensitivity and anti-interference towards Cu with the limit of detection (LOD) of 1.35 × 10 M. Job's plot analysis and MS spectroscopic study revealed the 2:1 complexation of probe 3c and Cu. In addition, probe 3c was successfully applied to the determination of Cu in real aqueous samples.
在此，通过邻氨基苯酚与苯甲醛、2,4-二氯苯甲醛和对二甲氨基苯甲醛以1:1摩尔比反应，设计并合成了三种席夫碱3a - c，它们在苯环上的取代基（-H、-Cl和-N(CH)）不同，产率分别为89 - 92%，效果良好。通过傅里叶变换红外光谱（FT - IR）、核磁共振（NMR）、基质辅助激光解吸电离质谱（MALDI - MS）和元素分析对其结构进行了表征。化合物3a和3b在乙醇/水体系中的荧光行为表现出严重的聚集诱导猝灭（ACQ）效应。相反，化合物3c在乙醇/水混合物（v/v = 1:1）中具有明显的J - 聚集诱导发射（AIE）特征，并且对铜表现出优异的灵敏度和抗干扰能力，检测限（LOD）为1.35×10⁻⁸ M。乔布氏曲线分析和质谱光谱研究表明探针3c与铜形成2:1的络合物。此外，探针3c已成功应用于实际水样中铜的测定。
