摘要/Abstract

以4-溴代三苯胺、5-甲醛基呋喃-2-硼酸和水杨酰肼为原料, 设计合成了一种新型的可快速识别Cu²⁺的席夫碱类荧光探针分子(HJW-2), 并通过¹H NMR,¹³C NMR和HR-MS对其结构进行了表征. 基于分子内电荷转移机理(ICT),HJW-2展现出优异的溶剂效应, 对Cu²⁺具有快速识别、高选择性和专一性, 检测限低至9.8×10^–8 mol•L^–1, 响应时间仅需10 s, 通过¹H NMR滴定实验和HRMS以及密度泛函理论计算, 对其可能的响应机理进行了探究. HJW-2已成功用于分析不同水样中的Cu²⁺浓度, 并且利用HJW-2在乙二胺四乙酸(EDTA)存在时的可逆性, 以Cu²⁺和EDTA为化学输入, 构建了分子逻辑门. 在实际应用中, 通过聚丙烯酰胺(PAM)掺杂HJW-2 (PAM-HJW-2)能实现对Cu²⁺的高效吸附, 去除率达到99.94%, 并通过扫描电子显微镜(SEM)和X光微区分析(EDS)对PAM-HJW-2吸附前后的微观形貌和元素变化进行了对比.
关键词: 荧光探针, 铜离子, 分子逻辑门, 吸附, 分子内电荷转移机理(ICT)
A novel Schiff base fluorescent probe (HJW-2) was designed and synthesized from 3-bromo-N,N-diphenylaniline, 5-formaldehyde-furan-2-boric acid and 2-hydroxybenzohydrazide. The structure of the probe molecule was confirmed by¹H NMR,¹³C NMR and HRMS. Based on the mechanism of intra-molecular charge transfer (ICT),HJW-2 shows excellent solvent effect.HJW-2 displayed efficiency, high selectivity, and specificity in the detection of Cu²⁺. The detection limit of HJW-2 on Cu²⁺ is as low as 9.8×10^–8 mol•L^–1, and the response time is only 10 s. The possible mechanism was studied by¹H NMR, HRMS and density functional theory (DFT) calculations.HJW-2 has been successfully used to analyze the content of Cu²⁺ in different water samples. Further, by utilizing the reversibility of HJW-2 in the presence of ethylene diamine tetraaccetic acid, the molecular logic gate is constructed with Cu²⁺ and EDTA as chemical inputs. Then, polyacrylamide (PAM) doping with HJW-2 (PAM-HJW-2) had high adsorption for Cu²⁺ and the removal rate was 99.94%. The micro-morphology of PAM-HJW-2 before and after adsorption was observed by scanning electron microscope (SEM) and energy dispersive spectrometer (EDS)
Key words: fluorescent probe, copper ions, molecular logic gate, adsorption, intra-molecular charge transfer (ICT)


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