Fabrication of Electrochemical Sensor for Dopamine and Uric Acid Based on a Novel Dimeric Phthalocyanine-involved Quintuple-decker Modified Indium Tin Oxide Electrode

doi:10.7503/cjcu20210582

Abstract

Abstract:

Combination between the extending π-conjugated system in the longitudinal and transverse directions of Pc macrocycles， sandwich-type ethylthio substituted phthalocyaninato europium complex ［Pc（SC₂H₅）₈］₂Eu₂· ［BiPc（SC₂H₅）₁₂］Eu₂［Pc（SC₂H₅）₈］₂ was synthesized. The self-assembled film of the complex was prepared by means of the solution-based Quasi-Langmuir-Shäfer（QLS） method. The molecular arrangement of the complex in the film was characterized by various spectroscopic methods. It was found that the molecules of the complex in the film were arranged on the substrate surface in the J-aggregation mode and edge-on configuration. The film was revealed to be a good semiconductor with conductivity as high as 8.86×10^-5 S/cm. ITO electrode modified by the QLS film of the complex was successfully applied in electrochemical detection， resulting in sensitive detection of dopamine（DA） and uric acid（UA） with the good sensitivities of 110 and 185.6 mA·μL·mol^-1·cm^-2 and low detection limits of 1.35 and 1.64 μmol/L for DA and UA， respectively.

Key words: Sandwich type rare earth phthalocyanine complex, Dopamine, Uric acid, Electrochemical sensor

CLC Number:

O657

TrendMD:

WEI Chuangyu, CHEN Yanli, JIANG Jianzhuang. Fabrication of Electrochemical Sensor for Dopamine and Uric Acid Based on a Novel Dimeric Phthalocyanine-involved Quintuple-decker Modified Indium Tin Oxide Electrode[J]. Chem. J. Chinese Universities, 2022, 43(1): 20210582.

Figures/Tables 10

Fig.1 Schematic molecular structures of [Pc(SC2H5)8]2·Eu2[BiPc(SC2H5)12]Eu2[Pc(SC2H5)8]2

Fig.2 Different pulse voltammogram(DPV) of complex 1 in CH2Cl2 at a scan rate of 20 mV/s

Fig.3 UV?Vis absorption spectra of complex 1 in CH2Cl2 solution and QLS flm(A), polarized UV?Vis spectra for complex 1 QLS film(B), out?of?plane XRD pattern(C) and I?V curve of QLS film(D) of complex 1（B） A∥ and A⊥ represent the absorbance for light polarized with the electric vector parallel and perpendicular to the dipping direction. 0° and 45° represent the angle between the light and the normal of the substrate， respectively；（C） the inset is the schematic representation of the complex 1 in the QLS film.

Fig.4 QLS film modified ITO electrode of complex 1(named as film/ITO) in 0.1 mol/L PBS, bare ITO and film/ITO in 0.1 mol/L PBS containing 0.1 mmol/L DA(A) and 0.1 mmol/L UA(B)

Fig.5 CV curves at the film/ITO in PBS containing the mixture of 0.1 mmol/L DA(A) and 0.1 mmol/L UA(B), and the corresponding plots of peak current versus scan rate(C, D)

Scheme 1 Schematic illustration of the reactions occurring at the film/ITO electrode surface

Fig.6 DPV curves at film/ITO in PBS(pH=7.3) with varying concentrations for DA(A) and UA(C), the corresponding calibration plots peak current vs. concentration(B, D)

Fig.7 DPV curves at film/ITO in PBS(pH=7.3) in concentration of 100 μmol/L DA and 100 μmol/L UA(A), DPV curves at film/ITO in PBS(pH=7.3) with varying concentrations for DA and UA(B), and the corresponding calibration plots for DA and UA(C)

Fig.8 Peak current from CVs vs. the storage time for the film/ITO in PBS with 100 μmol/L DA and 100 μmol/L UA

Table 1 Determination of DA and UA at electrode in real samples

Urine	Added/（μmol·L^-1）		Found/（μmol·L^-1）		Recovery（%）		RSD（%）
Urine	DA	UA	DA	UA	DA	UA	DA	UA
1	40	40	39.4	39.8	98.5	99.5	3.2	2.6
2	50	50	50.3	50.2	100.6	100.4	1.8	3.7
3	60	60	60.9	60.8	101.5	101.3	3.6	3.3

References 31

1	Chen X.， Li D. D.， Ma W. N.， Yang T. F.， Zhang Y. M.， Zhang D. D.， Microchim Acta， 2019， 186（7）， 1―10
2	Alwarappan S.， Liu G. D， Li C. Z.， Nanomed⁃Nanotechnol.， 2010， 6（1）， 52―57
3	Kurzątkowska K.， Sayin S.， Yilmaz M.， Radecka H.， Radecki J.， Sensors， 2017， 17（6）， 1368
4	Pramoda K.， Moses K.， Maitra U.， Rao C. N. R.， Electroanal.， 2015， 27（8）， 1892―1898
5	Chao M. Y.， Ma X. Y.， Xia L.， Int. J.Electrochem. Sci.， 2012， 7， 2201―2213
6	Zhang W. H.， Wei M.， Long Y. T.， Anal. Chem.， 2016， 88（10）， 5131―5136
7	Feng J. J.， Zhao Y. M.， Wang H. Y.， Chem. J.Chinese Univerisites， 2015， 36（7）， 1269―1274（冯娟娟，赵祎曼，王海燕. 高等学校化学学报， 2015， 36（7）， 1269―1274）
8	Zhang L. Y.， Qv S. F.， Wang Z. L.， Cheng J. K.， J. Chromatogr. B， 2003， 792（2）， 381―385
9	Zhang X.， Zhang Y. C.， Ma L. X.， Sens. Actuators B， 2016， 227， 488―496
10	Deng X.， Fang Y. S.， Lin S.， Cheng Q.， Liu Q. Y.， Zhang X. M.， ACS Appl. Mater. Interfaces， 2017， 9（4）， 3514―3523
11	Tang X. J.， Liu Q.， Wei C. Y.， Lv X. H.， Jin Z. C.， Chen Y. L.， Jiang J. Z.， J. Rare Earths， 2021， 39， 113―120
12	Yu Z. N.， Zou L.， Chen Y. L.， Jiang J. Z.， ACS Appl. Mater.Interfaces， 2016， 8（44）， 30398―30406
13	Xu H. Y.， Xiao J. J.， Yan L.， Zhu L. N.， Liu B. H.， J. Electroanal. Chem.， 2016， 779， 92―98
14	Wei C. Y.， Lu G.， Guo C.， Lv X. H.， Tang X. J.， Liu Q.， Cai X.， Chen Y. L.， Jiang J. Z.， Org. Electron.， 2021， 93， 106151
15	Lu G.， Kong X.， Sun J. S.， Zhang L. L.， Chen Y. L.， Jiang J. Z.， Chem. Commun.， 2017， 53， 12754―12757
16	Huang C. H.， Zhang Y.， Sun J. S.， Bian Y. Z.， Arnold D. P.， J. Porphyrins Phthalocyanines， 2000， 4， 588―590
17	Chen Y. L.， Bouvet M.， Sizun T.， Gao Y. N.， Plassard C.， Lesniewska E.， Jiang J. Z.， Phys. Chem. Chem. Phys.， 2010， 12， 12851―12861
18	Wang H. L.， Wang B. W.， Bian Y. Z.， Gao S.， Jiang J. J.， Coord. Chem. Rev.， 2016， 306， 195―216
19	Tang M. L.， Reichardt A. D.， Wei P.， Bao Z. N.， J. Am. Chem. Soc.， 2009， 131（14）， 5264―5273
20	Chen Y. L.， Kong X.， Lu G. F.， Qi D. D.， Wu Y. L.， Li X. Y.， Bouvet M.， Sun D. F.， Jiang J. Z.， Mater. Chem. Front.， 2018， 2， 1009―1016
21	Kasha M.， Rawls H. R.， El⁃bayoumi M. A.， Pure Appl. Chem.， 1965， 11， 371―392
22	Markovitsi D.， Tran⁃Thi T.， Even R.， Simon J.， Chem. Phy. Lett.， 1987， 137（2）， 107―112
23	Yoneyama M.， Sugi M.， Saito M.， Ikegami K.， Kuroda S.， Iizima S.， Jpn. J. Appl. Phys.， 1986， 25（7R）， 961―965
24	Wang X. Y.， Wang H. Q.， Ding X. F.， Wang X. Y.， Li X.， Chen Y. L.， Org. Electron.， 2017， 50， 389―396
25	Ahn H.， Chandekar A.， Kang B.， Sung C.， Whitten J. E.， Chem. Mater.， 2004， 16， 3274―3278
26	Cai X.， Wei C. Y.， Dong J. R.， Liu Q.， Wu Y. L.， Lu G.， Chen Y. L.， Jiang J. Z.， J. Mater. Sci.： Mater. Electron.， 2019， 30， 1976―1983
27	Parra V.， Brunet J.， Pauly A.， Bouvet M.， Analyst， 2009， 134（9）， 1776―1778
28	Li Q.， Huo C. R.， Yi K.， Zhou L. L.， Su L.， Hou X. M.， Sens. Actuators B， 2018， 260， 346―356
29	Zeng Y. L.， Li C. X.， Tang C. R.， Zhang X. B.， Shen G. L.， Yu R. Q.， Electroanalysis， 2006， 18， 440―448
30	Liu Q.， Zou L.， Sun Q. Q.， Li X. Y.， Chen Y. L.， Enzyme Microb. Technol.， 2020， 139， 109578
31	Huang L.， Jiao S. F.， Li M. G.， Electrochim. Acta， 2014， 121， 233―239

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