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

doi:10.6023/cjoc202008047

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1124-1130.DOI: 10.6023/cjoc202008047 Previous Articles Next Articles

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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

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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Abstract

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

Cite this article

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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Fig. & Tab. 12

Scheme 1. Synthesis route of probe TCF-Pyn

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)

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)

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

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)

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

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

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

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

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

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

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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Fig. & Tab. 12

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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