A Highly Stable Multi-response Zirconium(IV) Metal-Organic Frameworks for Fluorescence Sensing of Fe3+, Cr2O72- and Organic Small Molecules

doi:10.6023/cjoc202005010

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2938-2948.DOI: 10.6023/cjoc202005010 Previous Articles Next Articles

多响应锆基金属有机框架荧光传感器对Fe³⁺,Cr₂O₇^2-离子和有机小分子的识别

马学林^a,b, 韩利民^a, 张骁勇^b, 郝占忠^b, 杨威^b, 张玉恒^b, 王丽^b

a 内蒙古工业大学化工学院呼和浩特 010051;
b 包头师范学院化学学院内蒙古包头 014030

收稿日期:2020-05-05 修回日期:2020-07-01 发布日期:2020-07-17
通讯作者: 张骁勇, 韩利民 E-mail:66123@bttc.edu.cn;hanlimin@imut.edu.cn
基金资助:
国家自然科学基金（No.51964041）、内蒙古自然科学基金（Nos.2018BS02009，2019MS02031）、内蒙古教育厅项目（No.NJZY19187）和包头市青年创新人才（No.30324001）资助项目.

A Highly Stable Multi-response Zirconium(IV) Metal-Organic Frameworks for Fluorescence Sensing of Fe³⁺, Cr₂O₇^2- and Organic Small Molecules

Ma Xuelin^a,b, Han Limin^a, Zhang Xiaoyong^b, Hao Zhanzhong^b, Yang Wei^b, Zhang Yuheng^b, Wang Li^b

a Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051;
b Department of Chemistry, Baotou Teachers'College, Baotou, Inner Mongolia 014030

Received:2020-05-05 Revised:2020-07-01 Published:2020-07-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51964041), the Natural Science Foundation of Inner Mongolia (Nos. 2018BS02009, 2019MS02031), the Education Department Project of Inner Mongolia (No. NJZY19187), and the Young Innovative Talents in Baotou City (No. 30324001).

1. cjoc202005010.pdf(586KB)

Abstract

A new zirconium(IV) metal-organic framework (Zr-MOF) based on tricarboxylate ligands, namely ZrL▪2H₂O (L=2,2',2''-([1,3,5]-triazine-2,4,6-triimino)tribenzoic acid)) has been designed and synthesized. It can be served as a platform of multi-responsive fluorescence sensor for Fe³⁺ and Cr₂O₇^2- in water. The Stern-Volmer constants (K_SV) are 9.54×10⁴, 1.75×10⁴ L·mol^-1, and the limits of detection are 3.78×10^-8, 9.12×10^-7 mol/L, respectively. Meanwhile, it can also be used as a multi-response fluorescence probe to detect acetone, CCl₄ and xylene in N,N-dimethylformamide (DMF) solution. The Stern-Volmer constants (K_SV) are 6534.3, 4325.7, 4025.1 mL^-1, and the limits of detection are 1.09×10^-6, 2.73×10^-5, 3.17×10^-5 mL, respectively. The Zr-MOF was characterized by FTIR,¹H NMR, powder X-ray diffraction (PXRD), thermo gravimetric analysis (TGA) and elemental analysis. Interestingly, the Zr-MOF has the high water stability and pH stability, but its fluorescence intensity will show certain change law in the range of pH 0~14. Water and urine sample application test showed that Zr-MOF had high sensitive detection for Fe³⁺, and simulated organic solvents test showed that Zr-MOF has high sensitivity and selectivity to acetone, CCl₄ and xylene.

Key words: Zr-MOF, fluorescence sensor, Fe³⁺, Cr₂O₇^2-, acetone, CCl₄, xylene

Cite this article

Ma Xuelin, Han Limin, Zhang Xiaoyong, Hao Zhanzhong, Yang Wei, Zhang Yuheng, Wang Li. A Highly Stable Multi-response Zirconium(IV) Metal-Organic Frameworks for Fluorescence Sensing of Fe³⁺, Cr₂O₇^2- and Organic Small Molecules[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2938-2948.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Qiao, W. Z.; Song, T. Q.; Zhao, B. Chin. J. Chem. 2019, 37, 474.
[2] Zeng, J. Y.; Wang, X. S.; Zhang, X. Z.; Zhuo, R. X. Acta Chim. Sinica 2019, 77, 1156(in Chinese). (曾锦跃, 王小双, 张先正, 卓仁禧, 化学学报, 2019, 77, 1156.)
[3] Wang, X.; Zhang, Y.; Chang, Z.; Huang, H.; Liu, X. T.; Xu, J. L.; Bu, X. H. Chin. J. Chem., 2019, 37, 871.
[4] Liu, Z. L.; Li, W.; Liu, H.; Zhuang, X. D.; Li, S. Acta Chim. Sinica 2019, 77, 323(in Chinese). (刘治鲁, 李炜, 刘昊, 庄旭东, 李松, 化学学报, 2019, 77, 323.)
[5] Wang, B.; Yang, Q.; Guo, C.; Sun, Y. X.; Xie, L. H.; Li, J. R. ACS Appl. Mater. Interfaces 2017, 9, 10286.
[6] Li, L. N.; Shen, S. S.; Lin, R. Y.; Bai, Y.; Liu, H. W. Chem. Commun. 2017, 53, 9986.
[7] Luo, J.; Liu, B. S.; Cao, C.; Wei, F. Inorg. Chem. Commun. 2017, 76, 18.
[8] Guo, H.; Wu, N.; Xue, R.; Liu, H.; Li, L.; Wang, M. Y.; Yao, W. Q.; Li, Q.; Yang, W. Colloids Surf. A 2020, 585, 124094.
[9] Lv, R.; Chen, Z. H. Y.; Fu, X.; Yang, B. Y.; Li, H.; Su, J.; Gu, W.; Liu, X. J. Solid State Chem. 2018, 259, 67.
[10] Zhang, M. F.; Han, J.; Wu, H. P.; Wei, Q.; Xie, G.; Chen, S. P.; Gao, S. L. RSC Adv. 2016, 6, 94622.
[11] Wang, X.; Fan, W. D.; Zhang, M.; Shang, Y. Z.; Wang, Y. T.; Liu, D.; Guo, H. L.; Dai, F. N.; Sun, D. F. Chin. Chem. Lett. 2019, 30, 801.
[12] Huang, W. H.; Ren, J.; Yang, Y. H.; Li, X. M.; Wang, Q.; Jiang, N.; Yu, J. Q.; Wang, F.; Zhang, J. Inorg. Chem. 2019, 58, 1481.
[13] Tang, Y. Y.; Wang, C. J.; Chen, S.; Dai, H. Y. J. Coord. Chem. 2018, 70, 3996.
[14] Zhang, C. H.; Shi, H. Z.; Sun, L. B.; Yan, Y.; Wang, B. L.; Liang, Z. Q.; Wang, L.; Li, J. Y. Crys. Growth Des. 2018, 18, 7683.
[15] Wang, J. H.; Fan, Y. D.; Lee, H. W.; Yi, C. Q.; Cheng, C. M.; Zhao, X.; Yang, M. ACS Appl. Nano Mater. 2018, 1, 3747.
[16] Wang, B.; Yang, Q.; Guo, C.; Sun, Y. X.; Xie, L. H.; Li, J. R. ACS Appl. Mater. Interfaces 2017, 9, 10286.
[17] Gogoi, C.; Yousufuddin, M.; Biswas, S. Dalton Trans. 2019, 48, 1766.
[18] Jia, P.; Wang, Z. H.; Zhang, Y. F.; Zhang, D.; Gao, W. C.; Su, Y.; Li, Y. B.; Yang, C. L. Spectrochim. Acta. Part A 2020, 230, 118084.
[19] Su, Y.; Yu, J. H.; Li, Y. B.; Phua, S. F. Z.; Liu, G. F.; Lim, W. Q.; Yang, X. Z.; Ganguly, R.; Dang, C.; Yang, C. L.; Zhao, Y. L. Commun. Chem. 2018, 54, 1.
[20] Wen, G. X.; Wu, Y. P.; Dong, W. W.; Zhao, J.; Li, D. S.; Zhang, J. Inorg. Chem. 2016, 55, 10114.
[21] Xu, X. Y.; Yan, B. ACS Appl. Mater. Interfaces 2015, 7, 721.
[22] Zhu, S. Y.; Yan, B. Dalton Trans. 2018, 47, 1674.
[23] Chen, J.; Chen, H. Y.; Wang, T. S.; Li, J. F.; Wang, J.; Lu, X. Q. Anal. Chem. 2019, 91, 4331.
[24] Luo, J.; Liu, B. S.; Zhang, X. R.; Liu, R. T. J. Mol. Struct. 2019, 1177, 444.
[25] Gao, X. H.; Gao, Y. Y.; Qi, R. L.; Han, L. M. New J. Chem. 2019, 43, 18377.
[26] Hao, J. N.; Yan, B. Chem. Commun. 2015, 51, 7737.
[27] Wei, N.; Zhang, Y. R.; Han, Z. B. CrystEngComm 2013, 15, 8883.
[28] Wang, X. Q.; Feng, D. D.; Tang, J.; Zhao, Y. D.; Li, J.; Yang, J.; Kim, C. K.; Su, F. Dalton Trans. 2019, 48, 16776.
[29] Yang, S. L.; Yuan, Y. Y.; Sun, P. P.; Lin, T.; Zhang, C. X.; Wang, Q. L. New J. Chem. 2018, 42, 20137.
[30] Yi, K. Y.; Zhang, L. J. Hazard. Mater. 2020, 389, 122141.
[31] Zhang, Q. S.; Wang, J.; Kirillov, A. M.; Dou, W.; Xu, C.; Xu, C. L.; Yang, L. Z.; Fang, R.; Liu, W. S. ACS Appl. Mater. Interfaces 2018, 10, 23976.
[32] Huang, N. H.; Li, R. T.; Fan, C.; Wu, K. Y.; Zhang, Z.; Chen, J. X. J. Inorg. Biochem. 2019, 197, 110690.
[33] Zhao, S. L.; Xiao, J. N.; Zheng, T. X.; Liu, M. Y.; Wu, H. N.; Liu, Z. L. ACS Omega 2019, 4, 16378.
[34] Fan, C.; Lv, X. X.; Tian, M.; Yu, Q. C.; Mao, Y. Y.; Qiu, W. W.; Wang, H.; Liu, G. D. Microchim. Acta 2020, 187, 84.
[35] Ji, G. F.; Gao, X. C.; Zheng, T. X.; Guan, W. H.; Liu, H. T.; Liu, Z. L. Inorg. Chem. 2018, 57, 10525.
[36] Su, Y.; Zhang, D.; Jia, P.; Gao, W. C.; Li, Y. B.; Bai, Z. Y.; Liu, X.; Deng, Q. Y.; Xu, J.; Yang, C. L. Spectrochim. Acta. Part A 2019, 217, 86.
[37] Yang, C. L.; Xu, J.; Zhang, R.; Zhang, Y. F.; Li, Z. X.; Li, Y. W.; Liang, L. Y.; Lu, M. G. Sens. Actuators. B. 2013, 177, 437.
[38] Tang, S. F.; Hou, X. M. Cryst. Growth Des. 2019, 19, 45.
[39] Ding, B.; Liu, S. X.; Cheng, Y.; Guo, C.; Wu, X. X.; Guo, J. H.; Liu, Y. Y.; Li, Y. Inorg. Chem. 2016, 55, 4391.
[40] Sun, N. N.; Yan, B. Dyes Pigm. 2017, 142, 1.
[41] Li, C. R.; Hai, J.; Li, S. L.; Wang, B. D.; Yang, Z. Y. Nanoscale 2018, 10, 8667.
[42] He, H. M.; Zhu, Q. Q.; Li, C. P.; Du, M. Crys. Growth Des. 2019, 19, 694.
[43] Fan, K.; Bao, S. S.; Nie, W. X.; Liao, C.; Zheng, L. M. Inorg. Chem. 2018, 57, 1079.
[44] Tang, Y. L.; Chen, J. M.; Wu, H. F.; Yu, J. P.; Jia, J. L.; Xu, W.; Fu, Y. Y.; He, Q. G.; Cao, H. M.; Cheng, J. G. Dyes Pigm. 2020, 172, 107798.
[45] Cui, Y.; Chen, F.; Yin, X. B. Biosens. Bioelectron. 2019, 135, 208.
[46] Wu, J. X.; Yan, B. J. Colloid Interface Sci. 2017, 504, 197.
[47] Wang, T.; Liu, Q. H.; Gao, Y.; Yang, X. Y.; Yang, W. T.; Dang, S.; Sun, Z. M. Chin. Chem. Lett. 2016, 27, 497.
[48] Weng, H.; Yan, B. Sens. Actuators. B 2016, 28, 702.
[49] Wang, J.; Zha, Q. Q.; Qin, G. X.; Ni, Y. H. Talanta 2020, 2011, 120742.
[50] Xing, P. C.; Wu, D.; Chen, J. S.; Song, J. M.; Mao, C. J.; Gao, Y. H.; Niu, H. L. Analyst 2019, 144, 2656.
[51] Xu, Y. L.; Liu, Y.; Liu, X. H.; Zhao, Y.; Wang, P.; Wang, Z. L.; Sun, W. Y. Polyhedron 2018, 154, 350.
[52] Du, Q. Z.; Wu, P.; Dramou, P.; Chen, R.; He, H. New J. Chem. 2019, 43, 1291.
[53] Ji, S. J.; Ma, W.; Li, X. S.; An, J. D.; Zhang, H. M.; Li, Y.; Du, G. X.; Fei, L.; Lacoste, J. D.; Liu, J. J.; Wu, X. X.; Liu, Y. Y.; Yu, Z. Q.; Ding, B. Dyes Pigm. 2019, 167, 51.
[54] Zhao, X. X.; Wang, S. L.; Zhang, L. Y.; Liu, S. Y.; Yuan, G. Z. Inorg. Chem. 2019, 58, 2444.
[55] Lu, S. Q.; Liu, Y. Y.; Duan, Z. M.; Wang, Z. X.; Li, M. X.; He, X. Cryst. Growth Des. 2018, 18, 4602.
[56] Ye, Y. X.; Huang, C. J.; Yang, J.; Li, Y. S.; Zhuang, Q. X.; Gu, J. L. Microporous Mesoporous Mater. 2019, 284, 36.
[57] Zheng, H. Y.; Lian, X.; Qin, S. J.; Yan, B. ACS Omega 2018, 3, 12513.
[58] Zhang, X.; Xia, T. F.; Jiang, K.; Cui, Y. J.; Yang, Y.; Qian, G. D. J. Solid State Chem. 2017, 253, 277.
[59] El-Sewify, I. M.; Shenashen, M. A.; Shahat, A.; Yamaguchi, H.; Selimm, M. M.; Khalil, M. M. H.; El-Safty, S. A. J. Lumin. 2018, 198, 438.
[60] Li, Y. P.; Zhang, X.; Zhang, L.; Jiang, K.; Cui, Y. G.; Yang, Y.; Qian, G. D. J. Solid State Chem. 2017, 255, 97.
[61] Dalapati, R.; Balaji, S. N.; Trivedi, V.; Khamari, L.; Biswas, S. Sens. Actuators. B 2017, 245, 1039.
[62] SK, M.; Biswas, S. CrystEngComm 2016, 18, 3104.
[63] Xia, C.; Xu, Y.; Cao, M. M.; Liu, Y. P.; Xia, J. F.; Jiang, D. Y.; Zhou, G. H.; Xie, R. J.; Zhang, D. F.; Li, H. L. Talanta 2020, 212, 120795.
[64] Ma, X. L.; Han, L. M.; Zhang, X. Y.; Zhang, Y. H.; Wang, L.; Yang, K.; Ji, J. Chin. J. Org. Chem. 2020, 40, 1745(in Chinese). (马学林, 韩利民, 张骁勇, 张玉恒, 王丽, 杨坤, 冀婕, 有机化学, 2020, 40, 1745.)
[65] Wang, X. Q.; Feng, D. D.; Tang, J.; Zhao, Y. D.; Li, J.; Yang, J.; Kim, C. K.; Su, F. Dalton Trans. 2019, 48, 16776.

多响应锆基金属有机框架荧光传感器对Fe³⁺,Cr₂O₇^2-离子和有机小分子的识别

A Highly Stable Multi-response Zirconium(IV) Metal-Organic Frameworks for Fluorescence Sensing of Fe³⁺, Cr₂O₇^2- and Organic Small Molecules

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Chuntian Shi, Mei Yu, Aibin Wu, Jiangxiong Luo, Xiaojun Li, Ningchen Wang, Wenming Shu, Weichu Yu. A Water-Soluble Naphthalimide-Based Fluorescent Probe for Specific Sensing of Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2806-2813.
[2]	Shan Li, Lüqi Jiang. PhSO₃CH₂F: A New Reagent for O-Monofluoromethylation of Acetylacetone Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3798-3804.
[3]	Rongnan Yi, Dongxian Liu, Qilin Wu, Mingming Zhao, Yong Wang, Zheng Wang. Electrochemical Oxidated-Iodide Promoted α-H Aryl(alkyl)selenation of Acetone for the Preparation of α-Aryl(alkyl)selenoacetones [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3726-3732.
[4]	Fang Guo, Jun You, Wenju Wu, Yanchao Yu, Bin Jing, Bo Liu. Study on the Cyanide Substitution Reaction of Acetone Cannolhydrin as Cyanogen Source [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1968-1973.
[5]	Fang Guannian, You Jun, Yu Yanchao, Jing Junkai, Liu Bo, Wu Wenju. Study on the Reaction of Acetone Cyanohydrin with 3,5-Dimethyl-N-α,β-unsaturated Acyl Pyrazole [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2871-2878.
[6]	Liu Lingling, Yang Shan, Han Yi, Dai Chenyang, Shi Daqing, Huang Zhibin, Zhao Yingsheng. Rhodium-Catalyzed ortho-Alkenylation of Phenols Directed by Acetone Oxime Ether [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2394-2401.
[7]	Liu Xing, Tao Peng, Yang Jingjing, Liu Wen, Wang Hua, Wang Xuening, Zhao Qiang, Wong Wai-yeung, Xu Bingshe. Hydrophilic Fluorescent Probes for Fe³⁺ Ions Based on Nanoparticles of Twisting D-π-A Type Compound Derived from Benzylidenemalononitrile [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1588-1597.
[8]	Ma Xuelin, Han Limin, Zhang Xiaoyong, Zhang Yuheng, Wang Li, Yang Kun, Ji Jie. Triazine Derivative for Fluorescence Sensing of Zr⁴⁺, Fe³⁺ Ions and Acetone [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1745-1751.
[9]	Shen Jingru, Li Lihong, Wang Xiaogang, Zhang Jia'nan, Jiang Zhenglin. Green Synthesis of 2,2'-Bibenzazole and Its Polymers by Using Hexachloroacetone as C2 Synthon [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4322-4327.
[10]	Cao Xiying, Luo Shihe, Yang Chongling, Xiao Ying, Li Xiaoyan, Zhang Junru, Wang Zhaoyang. Research Progress of Organic Polymer Fluorescence Sensor [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4046-4059.
[11]	He Yuqian, Zhao Bing, Kan Wei, Wang Liyan, Song Bo, Yin Guangming, Bi Ye, Chen Shuwen. An Excited-State Intramolecular Proton Transfer (ESIPT) Plus Ag-gregation Induced Emission (AIE) Phenanthro[9, 10-d]imidazole-Based Fluorescence Probe for Detection of Fe³⁺ in Living Cells [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3250-3257.
[12]	Zhu Wenbo, Zhu Wei, Ding Jindong, Ma Xiaoqiang, Yao Hong, Zhang Youming, Lin Qi, Wei Taibao. A Novel Fluorescent Sensor Based on Aryl-furfural Functionalized Barbituric Acid for Recognition and Separation of Hg ²⁺/Fe ³⁺ [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2829-2834.
[13]	Jia Qifang, Zhu Lijuan, Fan Minghui, Li Quanxin. Catalytic Pyrolysis of Lignin for Directional Production of p-Xylene over Metal Oxides-Modified HZSM-5 Catalysts [J]. Chin. J. Org. Chem., 2018, 38(8): 2101-2108.
[14]	Zhang Youming, Han Bingbing, Lin Qi, Mao Pengpeng, Chen Jinfa, Yao Hong, Wei Taibao. Synthesis and Fe³⁺ Sensing Properties of the Chemosensor Based on Functionalized Naphthalimide Schiff Base Derivative [J]. Chin. J. Org. Chem., 2018, 38(7): 1800-1805.
[15]	Fu Yi, Tang Hui, Liu Ze, Zhang Wanxuan, Ren Jun. Synthesis and Properties of a Fluoride Ion Fluorescence Chemosensor [J]. Chin. J. Org. Chem., 2018, 38(7): 1806-1810.

多响应锆基金属有机框架荧光传感器对Fe3+,Cr2O72-离子和有机小分子的识别