Nghiên cứu tổng hợp vật liệu polymer in dấu phân tử (MIP) bằng phương pháp điện hóa, định hướng ứng dụng phát hiện dư lượng chất lượng kháng sinh

MINISTRY OF EDUCATION AND TRAINING HANOI UNIVERSITY OF SCIENCE AND TECHNOLOGY INTERNATIONAL TRAINING INSTITUTE FOR MATERIALS SCIENCE - VU VAN PHU ELECTROCHEMICAL SYNTHESIS OF MOLECULARLY IMPRINTED POLYMER (MIP), TOWARDS THE APPLICATION IN ANTIBIOTIC RESIDUE DETECTION MASTER THESIS OF MATERIALS SCIENCE Hanoi – 2018 MINISTRY OF EDUCATION AND TRAINING HANOI UNIVERSITY OF SCIENCE AND TECHNOLOGY INTERNATIONAL TRAINING INSTITUTE FOR MATERIALS SCIENCE - VU VAN PHU ELECTROCHEMICAL SYNTHESIS OF MOLECULARLY IMPRINTED POLYMER (MIP), TOWARDS THE APPLICATION IN ANTIBIOTIC RESIDUE DETECTION MASTER THESIS OF MATERIALS SCIENCE Batch ITIMS-2016 SUPERVISOR DR PHAM DUC THANH Hanoi – 2018 ACKNOWLEDGMENTS It is a pleasure to thank the many people who made this thesis possible First of all, I would like to express my sincere gratitude to my advisor Dr Pham Duc Thanh of the ITIMS Institute for the continuous support of my M.Sc study and research, for his patience, motivation, and immense knowledge I would also like to express my deepest thanks and sincere appreciation to Assoc Prof Mai Anh Tuan, MEMS/NEMS Laboratory – NACENTECH, for his valuable advice, constructive criticism, and his extensive discussions around my work, and lots of good ideas Especially, for the fantastic internship time he offered me at Tokyo University of Science - Japan, which brought me valuable experience and knowledge My sincere thanks also go to Dr Chu Thi Xuan, ITIMS for her untired help, and generous advice, and MSc Tran Quang Thinh of the MEMS/NEMS Laboratory – NACENTECH, for his support during my experimentation in the laboratory and contributed positively in the analysis and interpretation of data in my study I also thank MSc Nguyen Minh Hieu of the Nano and Energy Center for his devoted support and guidance during the fabrication process of electrochemical sensors in cleanroom, which helped me improve my skills very well I thank my fellow members in BIOMAT Group for the stimulating discussions, have made valuable comment suggestions on this thesis which gave me the inspiration to improve my assignment Last but not the least, I must express my very profound gratitude to members in my family for providing me with unfailing support and continuous encouragement throughout my years of study and through the process of researching this thesis This accomplishment would not have been possible without them Thank you! Hanoi, October 2018 i DECLARATION I hereby declare that matter embodied in this thesis entitled, “Electrochemical synthesis of molecularly imprinted polymer (MIP), towards the application in antibiotic residue detection” is a result of investigations carried out by me under the supervision and guidance of Dr Pham Duc Thanh of the International Training Institute for Materials Science (ITIMS), Hanoi University of Science and Technology I further declare that this thesis, to the best of my knowledge and belief, does not contain any data previously published by another person or submitted for the award of any degree or diploma at any other university or institute except where due reference is made in the text Author Vu Van Phu ii TABLE OF CONTENTS ACKNOWLEDGMENTS i DECLARATION ii LIST OF ABBREVIATIONS vi LIST OF TABLES viii LIST OF FIGURES ix INTRODUCTION .1 CHAPTER 1: THEORY & FUNDAMENTALS 1.1 Molecularly imprinted polymers 1.1.1 Types of imprinting mechanism 1.1.2 Removal of the imprinted template 1.1.3 Applications of MIPs 1.2 Polyaniline 1.2.1 Properties of PANi 12 1.2.1.1 Chemical properties 12 1.2.1.2 Optical properties .12 1.2.1.3 Thermal stability 12 1.2.1.4 Conductivity properties of PANi .12 1.2.2 Synthesis of PANi 14 1.3 Antibiotics: Chloramphenicol 16 1.4 Methods of electrochemical analysis 17 1.4.1 Cyclic voltammetry (CV) 17 1.4.2 Chronoamperometry (CA) .18 iii 1.4.3 Differential pulse voltammetry (DPV) .19 1.4.4 Fourier transform infrared spectroscopy (FT-IR) 19 CHAPTER 2: FABRICATION OF MIP-BASED ELECTROCHEMICAL SENSOR 21 2.1 Fabrication of electrochemical sensor 21 2.1.1 Photo-mask design 21 2.1.2 Fabrication processes of electrochemical sensors 22 2.1.3 Electrode surface pretreatment 27 2.2 Synthesis of CAP-imprinted PANi NWs 27 2.2.1 Chemical and instrumentation 27 2.2.2 Experimental schema .29 2.2.3 Electrochemical synthesis of PANi NWs .30 2.2.3.1 Synthesis of PANi NWs by CV method 30 2.2.3.2 Synthesis of PANi NWs by CA method 30 2.2.4 Synthesis of CAP-imprinted PANi NWs 30 2.2.5 Removal of CAP from CAP-imprinted PANi NWs 31 2.3 Detection of CAP by using MIP-based electrochemical sensor .31 CHAPTER 3: RESULTS AND DISCUSSIONS 32 3.1 Au electrode-based electrochemical sensor 32 3.2 Synthesis of PANI NWs 33 3.2.1 Synthesis of PANi NWs using CV technique 33 3.2.1.1 Effect of scanning potential ranges on CV-based polymerization 33 3.2.1.2 CV behavior of polymerization of aniline 35 iv 3.2.1.3 The effect of number of sweeps on the morphology of PANi 37 3.2.2 Synthesis of PANi NWs using CA technique 41 3.2.2.1 CA behavior of the polymerization of aniline 41 3.2.2.2 Effect of CA scanning time on the morphology of PANi 42 3.2.3 Choice of CA or CV for fabrication CAP-imprinted PANi NWs 45 3.3 MIP-based electrochemical sensor 47 3.3.1 CA behavior of synthesis of CAP-imprinted PANi NWs 47 3.3.2 The morphology of CAP-imprinted PANi .48 3.3.3 FT-IR spectrum of CAP-imprinted PANi 50 3.3.4 Removal of CAP from CAP-imprinted PANi 54 3.3.5 Electrochemical characteristics of the MIP-based sensor 56 3.3.5.1 CV behavior of the MIP-based sensor .57 3.3.5.2 DPV behavior of the MIP-based sensor 59 3.4 Detection of CAP-based on MIP sensor 61 CONCLUSIONS .64 REFERENCES 66 v LIST OF ABBREVIATIONS ANi Aniline CA Chronoamperometry CAP Chloramphenicol CE Counter electrode CPs Conductive polymers CV Cyclic voltammetry DPV Differential pulse voltammetry EB Emeraldine base ES Emeraldine salt FT-IR Fourier transform infrared microscopes GC-MS Gas chromatography-mass spectrometry HA Arbitrary acid HPLC High performance liquid chromatography LB Leucoemeraldine base LC-MS Liquid chromatography-mass spectrometry MIPs Molecularly imprinted polymers MRPL Minimum required performance limit NWs Nanowires PANi Polyaniline PANi NWs Polyaniline nanowires PB Pernigraniline base PR Photoresist vi PVD Physical vapor deposition RE Reference electrode SEM Scanning electron microscope TMAH Tetramethylammonium hydroxide UV Ultra violet WE Working electrode vii LIST OF TABLES Table 3.1 Data of the average diameter and length of PANi NWs by using CV .40 Table 3.2 Data of the average diameter and length of PANi NWs by using CA .45 Table 3.3 The CV parameters obtained from Figure 3.23 58 viii  The relationship between the peak currents and the CAP concentrations: The performance of the MIP-based electrochemical sensor was evaluated by determining CAP solution with a range of various concentration from 10-8 to 10-3 M The peak currents obtained from the DPVs corresponding to the concentration samples of CAP are expressed in the plot as shown in Figure 3.26 As seen in Figure 3.26, the peak current of the MIP-based sensor decreases when the concentration of CAP is diluted from 10-3 M to 10-8 M In this range of concentrations, the MIP-based sensor shows the linear relationship between Ipeak and log[CCAP] with the regression equation of Ipeak = 3.207 × log[CCAP] + 28.62 (R2 = 0.983) Figure 3.26 The calibration curve of the Ipeak with the CAP concentration The results also show that the minimum concentration of CAP, which was detected by the MIP-based electrochemical sensor, is experimentally determined at 10-8 M This concentration is converted to the ppb unit as equal to ppb 63 CONCLUSIONS This thesis reported the study of the MIP-based electrochemical sensor for the detection of chloramphenicol The main results were obtained as the following: Electrochemical sensors integrating three gold thin-film electrodes on the silicon wafer were fabricated by the cleanroom process The process produced 150 utilizable sensors, which show a success rate of 85% of 178 designed sensors on the mask The polymerization of aniline was investigated on the fabricated sensor by using cyclic voltammetry (CV) and chronoamperometry (CA) Both electrochemical techniques allow the deposition of polyaniline nanowires (PANi NWs) on the WE electrode CA was considered as a more advantageous technique for the PANi NWs synthesis, including short polymerization time and good surface morphology, in comparison with CV Using CA technique, the co-precipitation of chloramphenicol during the electro-polymerization of aniline was performed, which produced PANi NWs imprinting chloramphenicol molecules (MIP) The presence of chloramphenicol as the template molecule in MIP was demonstrated by FT-IR The results also shown that hydrogen bonding is the main interaction between chloramphenicol and PANi chains CA technique was also used for the removal of the template molecule to generate the cavities on the polymer matrix, which enables the specific recognition of chloramphenicol The removal of the template was demonstrated by electrochemical characterizations using CV and differential pulse voltammetry (DPV) The performance of the MIP-based electrochemical sensor was evaluated by determining CAP solution with concentrations vary from 10-8 to 10-3 M In this range of concentrations, the MIP-based sensor shows the linear relationship between 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bonding,... aquaculture includes compounds containing chloramphenicol (CAP) and restricted group residues including compounds in the tetracycline group (doxycycline, oxytetracycline, and tetracycline) So as