Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin Supramolecular Fluorescent Switch Constructed Based on Au3+ and I–

doi:10.6023/cjoc202111024

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1474-1482.DOI: 10.6023/cjoc202111024 Previous Articles Next Articles

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基于Au³⁺和I^–构建的单-(6-二乙烯三胺-6-去氧)-β-环糊精超分子荧光开关

鲁佳佳, 杨俊丽, 古捷, 杨举, 高振杰苏丽娇, 陶欣, 袁明伟^*(), 杨丽娟^*(), Lijuan Yang^*

云南民族大学化学与环境学院云南省高校智能超分子化学重点实验室生物基材料绿色制备技术国家地合工程中心昆明 650500

收稿日期:2021-11-15 修回日期:2022-01-17 发布日期:2022-01-27
通讯作者: 袁明伟, 杨丽娟, Lijuan Yang
基金资助:
国家自然科学基金(21762051); 云南省高校有机功能分子及材料科技创新团队和云南省教育厅科学研究基金资助项目

Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin Supramolecular Fluorescent Switch Constructed Based on Au³⁺ and I^–

Jiajia Lu, Junli Yang, Jie Gu, Ju Yang, Zhenjie Gao, Lijiao Su, Xin Tao(), Mingwei Yuan(), Lijuan Yang

Key Laboratory of Intelligent Supramolecular Chemistry at the University of Yunnan Province, National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry & Environment, Yunnan Minzu University, Kunming 650500

Received:2021-11-15 Revised:2022-01-17 Published:2022-01-27
Contact: Xin Tao, Mingwei Yuan, Lijuan Yang
Supported by:
National Natural Science Foundation of China(21762051); Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province and Yunnan Provincial Department of Education Science Research Fund

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Abstract

Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin (3N-β-CD) with the good water solubility was synthesized by a green and efficient method, and its structure was characterized by ¹H NMR and HRMS. 3N-β-CD was used as a fluorescent probe to detect 27 kinds of ions in aqueous solution. The results showed that the fluorescence of 3N-β-CD was quenched by Au³⁺ and I^–. The performance of 3N-β-CD for detecting Au³⁺ and I^– was further explored by fluorescence titration, Job curve, nuclear magnetic resonance, infrared spectroscopy, ion interference and time response. The results diplayed that the minimum detection limit of 3N-β-CD for Au³⁺ was 2.73×10^–6 mol/L and the binding stoichiometry ratios of 3N-β-CD with Au³⁺ was 1∶1, while the minimum detection limit of 3N-β-CD for I^– was 1.44×10^–6 mol/L and the binding stoichiometry ratios of 3N-β-CD with I^– was 2∶1. In addition, the fluorescence intensity of 3N-β-CD gradually recovered when I^– was added into the mixed solution of 3N-β-CD and Au³⁺. Interestingly, the fluorescence intensity of 3N-β-CD also gradually recovered when Au³⁺ was added into the mixed solution of 3N-β-CD and I^–. The results exhibited that Au³⁺ and I^– could be used as fluorescence “on-off-on” to control the fluorescence behavior of 3N-β-CD, and thus enabled Au³⁺ and I^– to detect each other. On this basis, the logic gate controlling 3N-β-CD fluorescence switch was designed. This work provides a new apporach for the research and application of 3N-β-CD as a fluorescence “on-off-on” sensor.

Key words: mono-6-diethylenetriamine-β-cyclodextrin, gold ion, iodine ion, fluorescent switch, logic gate

Cite this article

Jiajia Lu, Junli Yang, Jie Gu, Ju Yang, Zhenjie Gao, Lijiao Su, Xin Tao, Mingwei Yuan, Lijuan Yang. Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin Supramolecular Fluorescent Switch Constructed Based on Au³⁺ and I^–[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1474-1482.

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Fig. & Tab. 13

Figure 1. Schematic diagram of 3N-β-CD structure

Figure 2. Schematic diagram of supramolecular fluorescence sensing constructed by mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin and Au3+, I–

Figure 3. Fluorescence spectra of probe 3N-β-CD with cations and anions

Figure 4. (A) Spectra of the effect of Au3+ concentration on fluorescence intensity of 3N-β-CD; (B) Linear fitting curve of fluorescence intensity between Au3+concentration and 3N-β-CD; (C) Spectra of the effect of I– concentration on the fluorescence intensity of 3N-β- CD; (D) Linear fitting curve of fluorescence intensity between I– concentration and 3N-β-CD

Figure 5. (A) Job curve of 3N-β-CD and Au3+ and I–; (b) The binding mode of 3N-β-CD with Au3+ and I–

Figure 6. Time response of Au3+ and I– detected by 3N-β-CD

Figure 7. (A) Interference pattern of 26 ions on 3N-β-CD detection of Au3+; (B) Interference pattern of 26 ions on 3N-β-CD detection of I–

Figure 8. (A) Effect of I– concentration on the fluorescence intensity of 3N-β-CD and Au3+aqueous solution; (B) Fluorescence intensity of Au3+ concentration and 3N-β-CD and I– mixed aqueous solution affected the spectra

Figure 9. 1H-NMR spectra of 3N-β-CD and Au3+、I– (a) 3N-β-CD+I– (1.5×10–2 mol•L–1)+Au3+ (3.0×10–2 mol•L–1); (b) 3N-β-CD+I– (1.5×10–2 mol•L–1); (c) 3N-β-CD (1.5×10–2 mol•L–1); (d) 3N-β-CD+Au3+(3.0×10–2 mol•L–1); (e) 3N-β-CD+Au3+(3.0×10–2 mol•L–1)+I– (3.0×10–2 mol•L–1)

Figure 10. IR spectra of 3N-β-CD, 3N-β-CD mixed with Au3+, 3N-β-CD mixed with I–

Figure 11. Logical circuit diagram of IMPLICATION

Input	Output Fluorescence single
Au³⁺	I^–
0	0	1
1	0	0
0	1	0
1	1	1

Table 1. Truth table for the IMPLICATION logic gate

Figure 12. Fluorescence response in logic gates

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基于Au³⁺和I^–构建的单-(6-二乙烯三胺-6-去氧)-β-环糊精超分子荧光开关

Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin Supramolecular Fluorescent Switch Constructed Based on Au³⁺ and I^–

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