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

doi:10.6023/cjoc202102013

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2839-2847.DOI: 10.6023/cjoc202102013 Previous Articles Next Articles

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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

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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Abstract

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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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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Fig. & Tab. 15

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

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

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)

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

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)

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+

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

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

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

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

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

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

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

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

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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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