高选择性快速检测Cu2+的水杨酰腙型探针的合成及在逻辑门和吸附中的应用

doi:10.6023/cjoc202102013

有机化学 ›› 2021, Vol. 41 ›› Issue (7): 2839-2847.DOI: 10.6023/cjoc202102013 上一篇下一篇

研究论文

高选择性快速检测Cu²⁺的水杨酰腙型探针的合成及在逻辑门和吸附中的应用

何佳伟^a, 解正峰^a^,^b^,^*(), 薛松松^a, 刘宇程^a^,^b, 石伟^a, 陈鑫^c^,^*()

a 西南石油大学化学化工学院油气田应用化学四川省重点实验室成都 610500
b 西南石油大学工业危废处置与资源化利用研究院成都 610500
c 西南石油大学化学化工学院计算化学与分子模拟中心成都 610500

收稿日期:2021-02-02 修回日期:2021-03-10 发布日期:2021-03-25
通讯作者: 解正峰, 陈鑫
基金资助:
四川省青年科技创新研究团队(2020JDTD0018)

Synthesis of Salicylhydrazone Probe with High Selectivity and Rapid Detection Cu²⁺ and Its Application in Logic Gate and Adsorption

Jiawei He^a, Zhengfeng Xie^a^,^b(), Songsong Xue^a, Yucheng Liu^a^,^b, Wei Shi^a, Xin Chen^c()

a Oil & Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500
b Research Institute of Industrial Hazardous Waste Disposal and Resource Utilization, Southwest Petroleum University, Chengdu 610500
c Center for Computational Chemistry and Molecular Simulation, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500

Received:2021-02-02 Revised:2021-03-10 Published:2021-03-25
Contact: Zhengfeng Xie, Xin Chen
Supported by:
Sichuan Youth Science and Technology Innovation Research Team Project(2020JDTD0018)

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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)

引用此文

何佳伟, 解正峰, 薛松松, 刘宇程, 石伟, 陈鑫. 高选择性快速检测Cu²⁺的水杨酰腙型探针的合成及在逻辑门和吸附中的应用[J]. 有机化学, 2021, 41(7): 2839-2847.

Jiawei He, Zhengfeng Xie, Songsong Xue, Yucheng Liu, Wei Shi, Xin Chen. Synthesis of Salicylhydrazone Probe with High Selectivity and Rapid Detection Cu²⁺ and Its Application in Logic Gate and Adsorption[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2839-2847.

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图/表 15

图式1. 探针分子HJW-2的合成路线

Scheme 1. The synthetic route of probe HJW-2

Solvent	λ_abs/nm	λ_em/nm	Strength	Stokes shift/cm^–1
Toluene	395	462	4114	3671.4
Ethyl acetate	388	473	4499	4631.5
THF	389	476	4406	4698.5
Ethanol	394	509	3735	5734.3
Methanol	396	525	4149	6204.9

表1. 探针HJW-2在不同溶剂中的光学性质(λabs为最大吸收量和λem为最大发射量)

Table 1. Optical characteristics of HJW-2 in various solvents (λabs is absorption maximum and λem is emission maximum)

图1. 探针HJW-2在甲苯、乙酸乙酯、四氢呋喃、乙醇和甲醇中的吸收光谱(a)和发射光谱(b) (HJW-2: 1.0×10–5 mol•L–1, 狭缝: 5/5), 以及(c) 1×10–5 mol•L–1 HJW-2在不同极性的有机溶剂下紫外灯(365 nm)照射的图片

Figure 1. Absorption spectra (a) and emission spectra (b) of probe HJW-2 in toluene, ethyl acetate, tetrahydrofuran, ethanol and methanol (HJW-2: 1.0×10–5 mol•L–1, slit: 5/5), and (c) pictures of 1×10–5 mol•L–1 HJW-2 in organic solvents of different polarity under UV lamp (365 nm)

图2. HJW-2 (1×10–5 mol•L–1)在EtOH/H2O (V∶V=2∶3, 1×10–4 mol•L–1 Cys) 溶液中对不同金属阳离子(1×10–4 mol•L–1)的紫外-可见吸收光谱(a)和荧光光谱(b), 以及(c)在365 nm紫外灯下拍摄的照片

Figure 2. UV-visible absorption spectra (a) and fluorescence spectra (b) of HJW-2 (1×10–5 mol•L–1) in EtOH/H2O solution (V∶V=2∶3, 1×10–4 mol•L–1 Cys) on different metal cations (1×10–4 mol•L–1), and (c) pictures of various metal cations under 365 nm ultraviolet light

图3. HJW-2 (1×10–5 mol•L–1)在EtOH/H2O (V∶V=2∶3, 1×10–4 mol•L–1 Cys)溶液中Cu2+(1×10–4 mol•L–1)和金属离子(a)或阴离子(b) (1×10–4 mol•L–1)共存干扰实验图(激发波长420 nm)

Figure 3. Interference experiments with Cu2+ (1×10–4 mol• L–1) and other metal ions (a) or ionic ions (b) coexisting in EtOH/H2O (V∶V=2∶3, 1×10–4 mol•L–1 Cys) (λex=420 nm)

图4. (a) HJW-2 (1×10–5 mol•L–1)在EtOH/H2O (V∶V=2∶3, 1×10–4 mol•L–1 Cys)中对不同浓度的Cu2+响应的荧光光谱, (b) HJW-2 (1×10–5 mol•L–1)对处不同浓度的Cu2+在540 nm处响应的荧光点状图

Figure 4. (a) Fluorescence spectra of HJW-2 (1×10–5 mol• L–1) in EtOH/H2O (V∶V=2∶3, 1×10–4 mol•L–1 Cys) toward varying concentrations of Cu2+, (b) Dot diagram of the fluorescence responses of HJW-2 (1×10–5 mol•L–1) toward varying concentrations of Cu2+ at 540 nm Insert: magnified figure in the consistence scope of 0.5×10–6~3×10–6 mol•L–1 of Cu2+

图5. 探针HJW-2对Cu2+的响应时间

Figure 5. Response time of probe HJW-2 to Cu2+

图6. 探针HJW-2加入Cu2+的核磁滴定图

Figure 6. 1H NMR titration of HJW-2 after adding 1 equiv. of Cu2+ in DMSO-d6

图7. 探针HJW-2识别Cu2+可能的机理

Figure 7. Proposed plausible mechanisms for detection of Cu2+ by HJW-2

图8. HJW-2和HJW-2+Cu2+的优化结构和HOMO以及LUMO能级的电子云分布图

Figure 8. Optimized structures of HJW-2 and HJW-2+Cu2+ and electron distribution of the HOMO and LUMO energy levels

Sample	Add/ (µmol•L^–1)	Found/ (µmol•L^–1)	Recovery/%	R.S.D. (n=3)/%
Lake water	1.00	1.43	143.0	1.76
	2.00	2.45	122.5	1.87
	3.00	3.42	114.0	2.23
Tap water	1.00	1.15	115.0	1.89
	2.00	2.11	105.5	2.33
	3.00	3.18	106.0	1.95
Mineral water	1.00	0.98	98.0	2.96
	2.00	2.03	101.5	2.54
	3.00	3.06	102.0	2.41

表2. 不同水样中Cu2+的测定

Table 2. Determination of Cu2+ in different water samples

Entry	Input A (Cu²⁺)	Input B (EDTA)	Output (Fluorescence)
1	0	0	1
2	0	1	1
3	1	0	0
4	1	1	1

表3. 以Cu2+和EDTA为化学输入、荧光强度为输出的逻辑门真值表

Table 3. Logic gate truth table based on Cu2+ and EDTA as the chemical input and fluorescence intensity as the output

图9. 以Cu2+和EDTA为化学输入、荧光强度为输出的分子逻辑电路图

Figure 9. Molecular logic circuit diagram based on Cu2+ and EDTA as the chemical input and fluorescence intensity as the output

图10. 未吸附Cu2+的PAM-HJW-2自然光下的图片(a)和365 nm的紫外光下的图片(b), 以及已吸附Cu2+的PAM-HJW-2自然光下的图片(c)和365 nm的紫外光下的图片(d)

Figure 10. Images of PAM-HJW-2 under natural light (a) and 365 nm under ultraviolet light (b) without Cu2+ adsorption, respectively; images of PAM-HJW-2 under natural light (c) and 365 nm under ultraviolet light (d) with Cu2+ adsorbed, respectively

图11. PAM-HJW-2吸附Cu2+前的SEM (a)和EDS图 (b), 以及PAM-HJW-2吸附Cu2+后的SEM (c)和EDS图(d)

Figure 11. (a) SEM and (b) EDS micrographs before PAM-HJW-2 adsorption of Cu2+; (c) SEM and (d) EDS micrographs after PAM-HJW-2 adsorption of Cu2+

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高选择性快速检测Cu²⁺的水杨酰腙型探针的合成及在逻辑门和吸附中的应用

Synthesis of Salicylhydrazone Probe with High Selectivity and Rapid Detection Cu²⁺ and Its Application in Logic Gate and Adsorption

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