Citation: Tiantian MA, Sumei LI, Chengyu ZHANG, Lu XU, Yiyan BAI, Yunlong FU, Wenjuan JI, Haiying YANG. Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351 shu

Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine

Tiantian MA ¹ ,
Sumei LI ¹ ,
Chengyu ZHANG ¹ ,
Lu XU ¹ ,
Yiyan BAI ² ,
Yunlong FU ¹ ,
Wenjuan JI ^1,, ,
Haiying YANG ^{1, 2,,}

1.
Key Laboratory of Magnetic Molecules and Magnetic Information Materials, College of Chemistry and Materials Science, Shanxi Normal University, Taiyuan 030032, China
2.
Department of Applied Chemistry, Yuncheng University, Yuncheng, Shanxi 044000, China

Corresponding author: Wenjuan JI, jiwj@sxnu.edu.cn Haiying YANG, hyyang@ycu.edu.cn
Received Date: 22 September 2023
Revised Date: 30 January 2024

Figures(11)

A Cd-based metal-organic framework (MOF) [Cd(BDC)(BPZ)(H₂O)]_n (1), where BPZ=3,3′,5,5′-tetramethyl-1H,1′H-4,4′-bipyrazole and H₂BDC=terephthalic acid, was designed and synthesized. Compound 1 possesses a 3D pore structure with —CH₃ groups and free carboxyl oxygen atoms on the pore walls. The presence of methyl groups significantly enhances the hydrophobicity and stability of MOF. Moreover, the methyl group and uncoordinated carboxyl oxygen atoms can interact with dopamine (DA) molecules through hydrogen bonding or van der Waals interactions, endowing in 1 with sensitive electrochemical sensing properties for DA. The differential pulse voltammetry (DPV) test of the prepared 1/GCE electrode showed that it had a wide linear range of 0.4 to 764.7 μmol·L^-1 for detecting DA, and the detection limit was as low as 56.8 nmol·L^-1. The DPV response current of the electrode remained unchanged in the presence of common interferents. When the electrode was applied for real sample analysis, the recovery rates ranged from 95.23% to 100.90%.
- metal-organic framework,
- electrochemical sensing,
- dopamine
1. [1]
  Vaishag P V, Mohandas S A, Mufeeda M, Gangadharan P, Rasheed P A. Conversion of electronic waste to an electrochemical sensor for dopamine: Using MXene-modified liquid crystal display panels[J]. ACS Sustain. Chem. Eng., 2023,11(34):12771-12779. doi: 10.1021/acssuschemeng.3c03173
2. [2]
  Hardiansyah A, Saputra G M A, Hikmat H, Kusfarida Y E, Septiani N L W, Randy A, Hermawan A, Yuliarto B, Liu T Y, Kida T. Electrochemical evaluation of magnetic reduced graphene oxide nanosheet-modified glassy carbon electrode on dopamine electrochemical sensor for Parkinson's diagnostic application[J]. J. Chin. Chem. Soc., 2023,70(8):1665-1682. doi: 10.1002/jccs.202300197
3. [3]
  Chellasamy G, Arumugasamy S K, Nam M J, Venkateswarlu S, Varathan E, Sekar K, Manokaran K, Choi M J, Govindaraju S, Yun K. Experimental and simulation studies of bioinspired Au-enhanced copper single atom catalysts towards real-time expeditious dopamine sensing on human neuronal cell[J]. Chem. Eng. J., 2023,471144842. doi: 10.1016/j.cej.2023.144842
4. [4]
  Balkourani G, Brouzgou A, Tsiakaras P. A review on recent advancements in electrochemical detection of dopamine using carbonaceous nanomaterials[J]. Carbon, 2023,213(25)118281.
5. [5]
  Al-Salahi N O A, Hashem E Y, Abdel-Kader D A. Spectrophotometric methods for determination of dopamine hydrochloride in bulk and in injectable forms[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2022,278121278. doi: 10.1016/j.saa.2022.121278
6. [6]
  Roychoudhury A, Francis K A, Patel J, Jha S K, Basu S. A decoupler-free simple paper microchip capillary electrophoresis device for simultaneous detection of dopamine, epinephrine and serotonin[J]. RSC Adv., 2020,10(43):25487-25495. doi: 10.1039/D0RA03526B
7. [7]
  Alhusban A A, Hammad A M, Alzaghari L F, Shallan A I, Shnewer K. Rapid and sensitive HPLC-MS/MS method for the quantification of dopamine, GABA, serotonin, glutamine and glutamate in rat brain regions after exposure to tobacco cigarettes[J]. Biomed. Chromatogr., 2022,37(1)e5513.
8. [8]
  Afsharipour R, Dadfarnia S, Haji Shabani A M. Chemiluminescence determination of dopamine using N, P-graphene quantum dots after preconcentration on magnetic oxidized nanocellulose modified with graphene quantum dots[J]. Microchim. Acta, 2022,189(5)192. doi: 10.1007/s00604-022-05251-3
9. [9]
  Amara U, Mehran M T, Sarfaraz B, Mahmood K, Hayat A, Nasir M, Riaz S, Nawaz M H. Perylene diimide/MXene-modified graphitic pencil electrode-based electrochemical sensor for dopamine detection[J]. Microchim. Acta, 2021,188(7)230. doi: 10.1007/s00604-021-04884-0
10. [10]
  Abu Shama N, Asir S, Ozsoz M, Gokturk I, Turkmen D, Yilmaz F, Denizli A. Gold-modified molecularly imprinted N-methacryloyl-(l)-phenylalanine-containing electrodes for electrochemical detection of dopamine[J]. Bioengineering-Basel, 2022,9(3)87. doi: 10.3390/bioengineering9030087
11. [11]
  CHAI H M, YAN J L, REN Y X, GAO L J, ZHANG G Q, ZHANG Y, HAO S Y. Heterometallic Ln(Na)-MOFs (Ln=Tb, Dy, Ho): Crystal structures, luminescent sensing for acetaldehyde, Fe³⁺, Cr₂O₇^2-, and electrochemical sensing for catechol[J]. Chinese J. Inorg. Chem., 2021,37(11):1913-1921.
12. [12]
  Sofi F A, Bhat M A, Majid K. Cu²⁺-BTC based metal-organic framework: A redox accessible and redox stable MOF for selective and sensitive electrochemical sensing of acetaminophen and dopamine[J]. New J. Chem., 2019,43(7):3119-3127. doi: 10.1039/C8NJ06224B
13. [13]
  Song J J, Zheng J Z, Yang A N, Liu H, Zhao Z Y, Wang N X, Yan F. Metal-organic framework transistors for dopamine sensing[J]. Mater. Chem. Front., 2021,5(8):3422-3427. doi: 10.1039/D1QM00118C
14. [14]
  Hira S A, Nagappan S, Annas D, Kumar Y A, Park K H. NO₂-functionalized metal-organic framework incorporating bimetallic alloy nanoparticles as a sensor for efficient electrochemical detection of dopamine[J]. Electrochem. Commun., 2021,125107012. doi: 10.1016/j.elecom.2021.107012
15. [15]
  Zhou K F, Shen D F, Li X, Chen Y H, Hou L, Zhang Y S, Sha J Q. Molybdenum oxide-based metal-organic framework/polypyrrole nanocomposites for enhancing electrochemical detection of dopamine[J]. Talanta, 2020,209120507. doi: 10.1016/j.talanta.2019.120507
16. [16]
  Tang J, Liu Y, Hu J Q, Zheng S B, Wang X C, Zhou H P, Jin B K. Co-based metal-organic framework nanopinnas composite doped with Ag nanoparticles: A sensitive electrochemical sensing platform for simultaneous determination of dopamine and acetaminophen[J]. Microchem. J., 2020,155104759. doi: 10.1016/j.microc.2020.104759
17. [17]
  Chang Y N, Shen C H, Huang C W, Tsai M D, Kung C W. Defective metal-organic framework nanocrystals as signal amplifiers for electrochemical dopamine sensing[J]. ACS Appl. Nano Mater., 2023,6(5):3675-3684. doi: 10.1021/acsanm.2c05402
18. [18]
  REN S F, LÜ R, WANG Z L, CAO L, GUO T, LIU X H, FENG J. Research progress of MOFs-based electrochemical sensors and their detection application in the field of heavy-metal[J]. Chemical Reagents, 2023,45(10):101-109.
19. [19]
  Zorainy M Y, Alalm M G, Kaliaguine S, Boffito D C. Revisiting the MIL-101 metal-organic framework: Design, synthesis, modifications, advances, and recent applications[J]. J. Mater. Chem. A, 2021,9:22159-22217. doi: 10.1039/D1TA06238G
20. [20]
  Ma J P, Liu X L, Zheng J B, Bai W S. Electrochemical dopamine sensor based on bi-metallic Co/Zn porphyrin metal-organic framework[J]. Microchim. Acta, 2021,189(1)20.
21. [21]
  Tarasi S, Tehrani A A, Morsali A. The effect of methyl group functionality on the host-guest interaction and sensor behavior in metal-organic frameworks[J]. Sens. Actuator B-Chem., 2020,305127341. doi: 10.1016/j.snb.2019.127341
22. [22]
  Wang H M, Zhang X L, Wang S J, Ma H Y, Shen Y L, Wang X. A multifunctional electrochemical sensor for the simultaneous detection of ascorbic acid, dopamine, uric acid, and nitrite[J]. J. AOAC Int., 2021,104(3):860-866. doi: 10.1093/jaoacint/qsaa157
23. [23]
  Azharudeen A M, Roy A, Karthiga R, Prabhu S A, Prakash M G, Badhusha A M I, Ali H, Katubi K M, Islam M R. Ultrasensitive and selective electrochemical detection of dopamine based on CuO/PVA nanocomposite-modified GC electrode[J]. Int. J. Photoenergy, 20228755464.
24. [24]
  Ding Y, Zhao X, Wu P, Wang R, Xie L, Li Z, Zhu Z, Zhao H, Lan M. ZIF-67 MOF derived Co-based CeO₂ electrochemical sensor for dopamine[J]. Electrochim. Acta, 2023,463142802. doi: 10.1016/j.electacta.2023.142802
25. [25]
  Zhou Z, Mukherjee S, Hou S, Li W, Elsner M, Fischer R A. Porphyrinic MOF film for multifaceted electrochemical sensing[J]. Angew. Chem. Int. Ed., 2021,60(37):20551-20557. doi: 10.1002/anie.202107860
26. [26]
  Ma Y Y, Wei Z Y, Wang Y, Ding Y H, Jiang L P, Fu X, Zhang Y, Sun J, Zhu W X, Wang J L. Surface oxygen functionalization of carbon cloth toward enhanced electrochemical dopamine sensing[J]. ACS Sustain. Chem. Eng., 2023,9(18):16063-16072.
27. [27]
  Sipuka D S, Arotiba O A, Sebokolodi T I, Tsekeli T R, Nkosi D. Gold‐dendrimer nanocomposite based electrochemical sensor for dopamine[J]. Electroanalysis, 2023. doi: 10.1002/elan.202200099
28. [28]
  Radha G, Kumar K S, Chappanda K N, Aggarwal H. Zr-NDI MOF based optical and electrochemical dual sensor for selective detection of dopamine[J]. J. Phys. Chem. C, 2023,127(18):8864-8872. doi: 10.1021/acs.jpcc.3c01377
29. [29]
  Nisar A, Khan M A, Hussain Z. Synthesis and characterization of PANI/MOF-199/Ag nanocomposite and its potential application as non-enzymatic electrochemical sensing of dopamine[J]. J. Korean Ceram. Soc., 2022,59(3):359-369. doi: 10.1007/s43207-021-00166-w
30. [30]
  Abdel-Aziz A M, Hassan H H, Badr I H A. Activated glassy carbon electrode as an electrochemical sensing platform for the determination of 4-nitrophenol and dopamine in real samples[J]. ACS Omega, 2022,7(38):34127-34135. doi: 10.1021/acsomega.2c03427
31. [31]
  ZHANG Z J, ZHANG Y H, YANG S H, MENG W, SANG Z H. Preparation of Fe₂O₃/CuO/C based on Fe-Cu-MOF and its electrochemical sensing behaviors for dopamine[J]. Chinese Journal of Analysis Laboratory, 2022,41(7):770-775.
32. [32]
  Zahed M A, Barman S C, Toyabur R M, Sharifuzzaman M, Xuan X, Nah J, Park J Y. Ex situ hybridized hexagonal cobalt oxide nanosheets and RGO@MWCNT based nanocomposite for ultra-selective electrochemical detection of ascorbic acid, dopamine, and uric acid[J]. J. Electrochem. Soc., 2019,166(6):B304-B311. doi: 10.1149/2.0131906jes
33. [33]
  Cheng J, Li Y F, Zhong J, Lu Z W, Wang G T, Sun M M, Jiang Y Y, Zou P, Wang X X, Zhao Q B, Wang Y Y, Rao H B. Molecularly imprinted electrochemical sensor based on biomass carbon decorated with MOF-derived Cr₂O₃ and silver nanoparticles for selective and sensitive detection of nitrofurazone[J]. Chem. Eng. J., 2020,398125664. doi: 10.1016/j.cej.2020.125664
34. [34]
  Ali M, Sharma S, Singh R, Sharma K, Majhi S, Guin D, Tripathi C S P. Barium titanate nanocubes as a dual electrochemical sensor for detection of dopamine and acetaminophen[J]. J. Electrochem. Soc., 2022,169(6)067512. doi: 10.1149/1945-7111/ac7a67
35. [35]
  Aparna T K, Sivasubramanian R, Dar M A. One-pot synthesis of Au-Cu₂O/rGO nanocomposite based electrochemical sensor for selective and simultaneous detection of dopamine and uric acid[J]. J. Alloy. Compd., 2018,741:1130-1141. doi: 10.1016/j.jallcom.2018.01.205
36. [36]
  Marsilia M, Susmel S. Free-standing plastic electrodes: Formulation, electrochemical characterization and application to dopamine detection[J]. Sens. Actuator B-Chem., 2018,255:1087-1096. doi: 10.1016/j.snb.2017.08.052
37. [37]
  Chen X L, Zhang G W, Shi L, Pan S Q, Liu W, Pan H B. Au/ZnO hybrid nanocatalysts impregnated in N-doped graphene for simultaneous determination of ascorbic acid, acetaminophen and dopamine[J]. Mater. Sci. Eng. C, 2016,65:80-89. doi: 10.1016/j.msec.2016.03.106
38. [38]
  Zhang Q L, Feng J X, Wang A J, Wei J, Lv Z Y, Feng J J. A glassy carbon electrode modified with porous gold nanosheets for simultaneous determination of dopamine and acetaminophen[J]. Microchim. Acta, 2015,182:589-595. doi: 10.1007/s00604-014-1363-x
1. [1]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
2. [2]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
3. [3]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
4. [4]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
5. [5]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
6. [6]
  Jiahong ZHENG , Jingyun YANG . Preparation and electrochemical properties of hollow dodecahedral CoNi₂S₄ supported by MnO₂ nanowires. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1881-1891. doi: 10.11862/CJIC.20240170
7. [7]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
8. [8]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
9. [9]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
10. [10]
  Shasha Ma , Zujin Yang , Jianyong Zhang . Facile Synthesis of FeBTC Metal-Organic Gel and Its Adsorption of Cr₂O₇²⁻: A Physical Chemistry Innovation Experiment. University Chemistry, 2024, 39(8): 314-323. doi: 10.3866/PKU.DXHX202401008
11. [11]
  Kun Xu , Xinxin Song , Zhilei Yin , Jian Yang , Qisheng Song . Comprehensive Experimental Design of Preferential Orientation of Zinc Metal by Heat Treatment for Enhanced Electrochemical Performance. University Chemistry, 2024, 39(4): 192-197. doi: 10.3866/PKU.DXHX202309050
12. [12]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
13. [13]
  Jiarong Feng , Yejie Duan , Chu Chu , Dezhen Xie , Qiu'e Cao , Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016
14. [14]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
15. [15]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
16. [16]
  Jie ZHANG , Xin LIU , Zhixin LI , Yuting PEI , Yuqi YANG , Huimin LI , Zhiqiang LIU . Assembling a luminescence silencing system based on post-synthetic modification strategy: A highly sensitive and selective turn-on metal-organic framework probe for ascorbic acid detection. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 823-833. doi: 10.11862/CJIC.20230310
17. [17]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
18. [18]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
19. [19]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
20. [20]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(136)
HTML views(22)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142