2-[3-氰基呋喃-2(5H)-亚基]丙二腈衍生物的合成及其对Pd2+的识别

doi:10.6023/cjoc202008047

有机化学 ›› 2021, Vol. 41 ›› Issue (3): 1124-1130.DOI: 10.6023/cjoc202008047 上一篇下一篇

研究论文

2-[3-氰基呋喃-2(5H)-亚基]丙二腈衍生物的合成及其对Pd²⁺的识别

钟克利^a, 周璐璐^a, 陈琳^a, 汤立军^a^,^*(), 高雪^b, 刘秀英^b, 庞秀秀^c, 燕小梅^c^,^*()

a 渤海大学化学与材料工程学院辽宁锦州 121013
b 渤海大学食品科学与工程学院生鲜农产品贮藏加工及安全控制技术国家地合工程研究中心辽宁锦州 121013
c 大连医科大学检验医学院辽宁大连 116044

收稿日期:2020-08-25 修回日期:2020-11-03 发布日期:2020-11-12
通讯作者: 汤立军, 燕小梅
基金资助:
国家自然科学基金(21878023); 国家自然科学基金(U1608222); 辽宁省自然科学基金指导计划(2020-MS-289); 辽宁省自然科学基金指导计划(20180551195); 辽宁特聘教授支持计划资助项目.

Synthesis of 2-(3-Cyanofuran-2(5H)-ylidene)malononitrile Derivative and Its Recognition for Pd²⁺

Keli Zhong^a, Lulu Zhou^a, Lin Chen^a, Lijun Tang^a^,^*(), Xue Gao^b, Xiuying Liu^b, Xiuxiu Pang^c, Xiaomei Yan^c^,^*()

a College of Chemistry and Material Engineering, Bohai University, Jinzhou, Liaoning 121013
b National & Local Joint Engineering Research Center of Storage, Processing and Safety Control Technology for Fresh Agricultural and Aquatic Products, College of Food Science and Technology, Bohai University, Jinzhou, Liaoning 121013
c College of Laboratory Medicine, Dalian Medical University, Dalian, Liaoning 116044

Received:2020-08-25 Revised:2020-11-03 Published:2020-11-12
Contact: Lijun Tang, Xiaomei Yan
About author:
* Corresponding authors. E-mail: ljtang@bhu.edu.cn;
xmyan1978@sina.com
Supported by:
National Natural Science Foundation of China(21878023); National Natural Science Foundation of China(U1608222); Natural Science Foundation of Liaoning Province(2020-MS-289); Natural Science Foundation of Liaoning Province(20180551195); Program for Distinguished Professor of Liaoning Province.

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摘要/Abstract

通过两步反应合成了一种2-(3-氰基呋喃-2(5H)-亚甲基)丙二腈衍生物TCF-Pyn, 该化合物在MeCN/磷酸缓冲容溶液(PBS) (V∶V=2∶8, PBS 2×10^–2 mol/L, pH=7.4)混合溶液中能高选择性荧光“OFF-ON”识别Pd²⁺, 发射波长达到近红外区(653 nm). 该探针具有较好的抗干扰能力、较宽的pH适用范围(3~8)和较低的检测限(6.92 μmol/L). 应用研究表明, TCF-Pyn能检测真实水样中的Pd²⁺, 并可对活细胞中的Pd²⁺进行荧光成像.

关键词: 荧光探针, 近红外发射, 识别, Pd²⁺, 细胞成像

2-(3-Cyano-furan-2(5H)-methylene)malononitrile derivative (TCF-Pyn) was synthesized by a two-step reaction. Compound TCF-Pyn could recognize Pd²⁺ with a high selectivity, “OFF-ON” fluorescent response and the near-infrared emission (653 nm) in MeCN/PBS ( V∶V=2∶8, PBS 2×10^–2 mol/L, pH=7.4) solution. The probe possesses a good anti- interference capability, a wide pH range (3~8) and a low detection limit (6.92 μmol/L). The application research showed that TCF-Pyn could detect Pd²⁺ in real water samples and fluorescent image Pd²⁺in living cells.

Key words: fluorescent probe, near-infrared emission, recognition, Pd²⁺, cell imaging

引用此文

钟克利, 周璐璐, 陈琳, 汤立军, 高雪, 刘秀英, 庞秀秀, 燕小梅. 2-[3-氰基呋喃-2(5H)-亚基]丙二腈衍生物的合成及其对Pd²⁺的识别[J]. 有机化学, 2021, 41(3): 1124-1130.

Keli Zhong, Lulu Zhou, Lin Chen, Lijun Tang, Xue Gao, Xiuying Liu, Xiuxiu Pang, Xiaomei Yan. Synthesis of 2-(3-Cyanofuran-2(5H)-ylidene)malononitrile Derivative and Its Recognition for Pd²⁺[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1124-1130.

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图/表 12

图式1. 探针TCF-Pyn的合成路线

Scheme 1. Synthesis route of probe TCF-Pyn

图1. TCF-Pyn (10 μmol/L)的MeCN/PBS (V∶V=2∶8, pH=7.4)溶液中加入各种阳离子后的荧光光谱(λ ex=550 nm)

Figure 1. Fluorescence spectrum of TCF-Pyn (10 μmol/L) in MeCN/PBS (V∶V=2∶8, pH=7.4) solution upon addition of various metal cations (λ ex=550 nm)

图2. 不同浓度的Pd2+ (0~80 μmol/L)加入到TCF-Pyn (10 μmol/L)的MeCN/PBS (V∶V=2∶8, pH=7.4)溶液中的荧光光谱变化(λ ex=550 nm)

Figure 2. Fluorescence spectrum of TCF-Pyn (10 μmol/L) in MeCN/PBS (V∶V=2∶8, pH=7.4) solution upon addition different amounts of Pd2+ (0~80 μmol/L) (λ ex=550 nm)

图3. 探针TCF-Pyn的荧光比值对log{[Pd2+]/(mol?L–1)}的线性关系

Figure 3. Linear relationship of fluorescence ratio of TCF-Pyn against log{[Pd2+]/(mol?L–1)}

图4. 在各种阳离子(80 μmol/L)存在下TCF-Pyn (10 μmol/L)对Pd2+ (80 μmol/L)识别的抗干扰能力

Figure 4. Anti-interference ability of TCF-Pyn (10 μmol/L) recognition for Pd2+ (80 μmol/L) in the presence of various cations (80 μmol/L)

图5. 在365 nm手提式紫外灯照射下探针TCF-Pyn, TCF- Pyn+Pd2+及化合物TCF-OH薄层析色谱图

Figure 5. TLC chromatogram of TCF-Pyn, TCF-Pyn+Pd2+and TCF-OH under the irradiation of 365 nm portable UV lamp

图6. 探针TCF-Pyn+Pd2+在乙腈中的高分辨质谱

Figure 6. HRMS spectrum of compound TCF-Pyn+Pd2+ in MeCN

图式2. 探针TCF-Pyn识别Pd2+可能的机理

Scheme 2. Possible mechanism of TCF-Pyn sensing Pd2+

图7. TCF-Pyn和TCF-Pyn+Pd2+在不同pH下的荧光变化

Figure 7. Fluorescence changes of TCF-Pyn and TCF-Pyn+Pd2+ at different pH

图8. 在实际水样中探针TCF-Pyn (10 μmol/L)的荧光强度随Pd2+浓度(5~35 μmol/L)的变化

Figure 8. Linear fluorescence intensities of TCF-Pyn (10 μmol/L) upon addition of Pd2+ (5~35 μmol/L) in three real water samples

Sample	Added/ (μmol?L^–1)	Found/ (μmol?L^–1)	Recovery rate/%	CV (n=3)
Tap water	10	9.82	98.2	0.04
	20	20.33	101.6	0.22
	30	30.71	102.4	0.14
Lake water	10	9.74	97.4	0.32
	20	18.49	92.4	0.11
	30	30.50	101.7	0.07
River water	10	10.42	104.2	0.51
	20	21.48	107.4	0.20
	30	30.30	101.0	0.19

表1. 实际水样中Pd2+的检测结果a

Table 1. Detection results of Pd2+ in actual water samples

图9. 在MCF-7细胞中探针TCF-Pyn对Pd2+荧光成像

Figure 9. Fluorescence images of TCF-Pyn for Pd2+ in MCF-7 cells The cells were only incubated with probeTCF-Pyn (10 μmol/L) for 30 min. (a) 0, (b) 10, (c) 30, (d) 50, (e) 100 μmol/L of Pd2+ were added into the cells reincarnated with TCF-Pynand further incubated for 30 min. Images from left to right: bright field, fluorescence field and merged images

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2-[3-氰基呋喃-2(5H)-亚基]丙二腈衍生物的合成及其对Pd²⁺的识别

Synthesis of 2-(3-Cyanofuran-2(5H)-ylidene)malononitrile Derivative and Its Recognition for Pd²⁺

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