臺灣博碩士論文加值系統

This thesis describes the oxygen, boronic acid functionalization of screen printed carbon electrode (SPCE) and utilization of those functional moieties for versatile sensor applications. In-situ generated oxygen functionalities along with edge/defect sites of preanodized SPCE (SPCE*) is used for metal free oxidation of poly aromatic hydrocarbons (PAHs). In later sections, we report preparation of stimuli responsive boronic acid based probes on SPCE via both electrochemical as well as chemical routes. In the electrochemical method, 4-Aminophenylboronic acid (4-APBA) has been dimerized and polymerized on SPCE and SPCE* with or without fluoride. The dimer-modified electrode possesses dual functionalities (R-N=N-R' and -B(OH)2) which makes its suitable for selective detection of hypochlorite (i.e., free chlorine), fluoride and sugar molecules, respectively. In chemical method, a new approach for rapid oxidative polymerization of aminophenylboronic acid is described via reduction of surface oxygen functional groups of SPCE* and boron-phosphate complexation. The resulting polymer possesses nanofiber morphology with multiple functional moieties such as imine, azo and boronic acid (-NH+-, -N=N- and -B(OH)2. This has been utilized for direct electro-catalytic detection of Free-Cl, NADH and indirect detection of fluoride ion and fructose by using Fe(CN)63-/4- as redox probe. In continuation of above studies, a voltammetric sensor for determination of phosphate anion (Pi) was developed on the screen printed carbon electrode/anthracene boronic acid (SPCE/ANBA) modified electrode. The complexation of ANBA with Pi through specific BA-Pi binding could cause the quinone formation, which was utilized for Pi detection.

CHAPTER 1 1
1.1. Research goals and thesis organization 1
1.2. General introduction of electrochemistry 5
1.3. Electrochemical cell 5
1.4. Thermodynamics of cell potentials 6
1.5. The faradaic and non-faradaic reaction 7
1.6. Voltammetry 8
1.7. Chemically modified electrodes (CMEs) 9
1.7.1. Electrode activation 10
1.7.2. Preanodization (Oxygen functionalization) 11
1.7.3. Effect of preanodization medium 11
1.7.4 Boronic acid functionalization 12
1.8. Experimental Section 15
1.8.1 Electrodes and instrumentation 15
CHAPTER 2 17
Role of defect sites and oxygen functionalities on preanodized screen printed carbon electrode for adsorption and oxidation of polyaromatic hydrocarbons 17
2.1. Introduction 17
2.2. Materials and methods 18
2.3. Results and discussion 18
2.4. Conclusion 28
CHAPTER 3 29
A dually functional 4-aminophenylboronic acid dimer for voltammetric detection of hypochlorite, glucose and fructose 29
3.1. Introduction 29
3.2. Experimental 30
3.2.1. Materials and methods 30
3.2.2. Electrode preparation 31
3.3 Results and discussion 31
3.3.1 Electropolymerization and dimerization of 4-aminophenylboronic acid 31
3.3.2 Scan rate and pH study 36
3.3.3 Detection of sugar molecules 37
3.3.4 Detection of hypochlorite 40
3.3.5 Real sample analysis 46
3.4 Conclusion 48
CHAPTER 4 49
Electrochemical detection of fluoride ions using 4-aminophenyl boronic acid dimer modified electrode. 49
4.1 Introduction 49
4.2 Chemicals and Instrumentation 51
4.3 Results and discussions 52
4.3.1 Electrode preparation and characterization by CV 52
4.3.2 Surface characterization of dimer and polymer on AuSPE by SEM and UV. 54
4.3.3 Functional group characterization by XPS 56
4.3.4 Detection of fluoride ions at SPCE*-APBAD modified electrode 56
4.3.5 Density Functional Theory (DFT) calculations 58
4.3.6 Mechanism of fluoride detection 60
4.3.7 FIA detection of Fluoride 61
4.3.8 Real sample analysis 64
4.4. Conclusions 66
CHAPTER 5 67
Fluoride-free synthesis of poly(aminophenylboronic acid) nanofiber on carbon electrode for sensor applications 67
5.1 Introduction 67
5.2 Materials and methods 69
5.2.1 Chemicals 69
5.2.2 Instrumentation 69
5.2.3 Electrode preparation 70
5.3. Results and discussion 70
5.3.1 Electrochemical behavior of APBA modified electrodes 70
5.3.2 Investigating role of oxygen functionalities 72
5.3.3 DFT calculations 75
5.3.4 Effect of preanodization time and phosphate concentration 77
5.3.5 Characterization of PAPBA modified electrode by SEM 78
5.3.6 Characterization by UV-visible and X-ray photoelectron spectroscopy 80
5.3.7 Method validation by using 3-APBA polymerization on SPCE* 81
5.3.8 Sensor applications 82
5.4 Conclusion 84
CHAPTER 6 85
Anthracene Boronic Acid Functionalization of Activated Carbon Electrode: A Strategy for Direct Phosphate Voltammetric Detection using Quinone Formation. 85
6.1 Introduction 85
6.2. Materials and methods 87
6.2.1 Chemicals 87
6.2.2 Instrumentation 88
6.2.3 Electrode preparation 88
6.2.4 Real sample preparation 89
6.3 Results and discussions 89
6.3.1 Electrochemical behavior of AN, ANBA and ANBA-Pi modified SPCE 89
6.3.2 The role of oxygen functionalities of electrode 90
6.3.3 Characterization of SPCE/AQBA-Pi complex by X-ray photoelectron spectroscopy 91
6.3.4 Density Functional Theory (DFT) calculations of ANBA and ANBA-Pi 92
6.3.5 Determination of Pi by SWV 94
6.3.6 Real sample analysis 96
6.4 Conclusions 97
Chapter 7 98
Over all conclusions 98
List of publications 100
References 101

 
List of Figures
Figure 1. 1 Schematic representation of AN oxidation on SPCE 2
Figure 1. 2 Schematic representation of APBA dimerization on SPCE* 2
Figure 1. 3 Schematic representation of fluoride detection by using APBAD modified SPCE 3
Figure 1. 4 Schematic representation of APBA polymerization on SPCE* 3
Figure 1. 5 Schematic representation of quinone formation in presence and absence of phosphate. 4
Figure 1. 6 The number of boronic acid based papers published from 2000 (data obtained from Reaxys) 13
Figure 1. 7 Screen printed carbon electrode 15
Figure 1. 8 Construction of SF100 flow cell with three electrode system Reference electrode (A), Working electrode (SPCE) (B), Counter electrode (C), Main body of SF100 (D), Inlet (E), Outlet (F) and pictorial representation of flow injection analysis system. 16

Figure 2. 1 Cyclic voltammograms of AN oxidation at SPCE (A), and PBS-SPCE* (B), Corresponding cyclic voltammograms after medium exchange in 0.1 M, pH 7 PBS (C&D). 19
Figure 2. 2 Cyclic voltammograms scan rate study in pH 7 PBS and pH study AQ modified SPCE* (A &C), corresponding graphs (B&D). 20
Figure 2. 3 Raman spectra of SPCE and SPCE* (A), Raman image of defect band intensity (B). 21
Figure 2. 4 Raman spectra of various SPCE* (A), Plots of amount of defect (ID/IG) generated from preanodization in various electrolytes versus their corresponding surface coverage (B). 21
Figure 2. 5 C1s-XPS for various preanodized SPCE electrodes in 0.1 M, HCl (A), pH 7 PBS (B), H2SO4 (C), HNO3 (D). 22
Figure 2. 6 Carbonyl group generated from preanodization in various electrolytes versus their corresponding surface coverage, comparison table and AQ surface coverage bar diagram of various SPCE*. 23
Figure 2. 7 Raman spectra (A), AN oxidation CVs (B), and plot of amount of defect (ID/IG) generated versus their corresponding surface coverage against different preanodization time (C). 24
Figure 2. 8 Raman spectra of SPCE* before and after ACN coating 24
Figure 2. 9 Cyclic voltammogram of electrochemical reduction of SPCE* (A), Raman and XPS spectra of (a) SPCE*, (b) ERSPCE* (B&C), CVs of AN electrochemical oxidation behavior on ER-SPCE* under the restricted and extended potential window in 0.1 M, pH 7 PBS (D). 25
Figure 2. 10 LC–MS spectrum of AN obtained before/after electro-oxidation from different electrodes. 26
Figure 2. 11 Cyclic voltammograms of naphthalene (Nph) and tetracene (TC) oxidation on SPCE (A&B), (dotted line) and SPCE* (solid line) after medium exchange in 0.1 M, pH 7 PBS , dashed line obtained on SPCE* without Nph and TC. 27

Figure 3. 1 Cyclic voltammograms of 4-aminophenylboronic acid in the absence/presence of 20 mM F ─ ions at SPCE and SPCE* in 0.1 M HCl (A), Resolved N1s XPS spectra of as-formed electrode in the absence of F ─ ions at SPCE* (B). 32
Figure 3. 2 Schematic representation of the dimer/polymer preparation of the proposed system. 33
Figure 3. 3 Electrochemical dimerization of 1 mM 4-aminophenylboronic acid in the 0.1 M, pH 7 PBS at SPCE* 34
Figure 3. 4 Stability of dimer modified SPCE* electrode in 0.1 M, pH 7 PBS. 35
Figure 3. 5 Scan rate study of dimer modified electrode in 0.1 M, pH 7 PBS, Scan rate varied between 0.01 and 0.25 V/s (A), Corresponding Laviron's plot (B), pH study of dimer modified electrode in range between pH 2 and pH 10 (C), Corresponding pH verses E1/2 plot (D). 37
Figure 3. 6 Cyclic voltammograms of the dimer-modified electrode in the absence/presence of 1 mM fructose in 5 mM Fe(CN)64–/3- containing 0.1 M phosphate buffer solution at pH 5 (A), pH 7.4 (B), pH 9 (C). 38
Figure 3. 7 Differential pulse voltammograms and the corresponding calibration plot obtained with the dimer-modified electrode upon addition of increasing concentrations fructose (A) and glucose (B) in 0.1 M, pH 7 PBS containing 5 mM Fe(CN)64–/3–, Observed current changes in presence of 100 µM fructose or Glucose with/without 200 µM common AA and UA interferents (C) [error bar diagram represents the standard deviations (n=3) of current change]. 39
Figure 3. 8 Differential pulse voltammograms of dimer-modified electrode in the presence of 100 µM fructose/glucose with/without 200 μM AA and UA. 40
Figure 3. 9 Cyclic voltammograms of the dimer-modified electrode in the absence/presence of 2 mM hypochlorite in 0.1 M pH 4.8 (A), pH 6 (B), pH 7 (C) and pH 8 (D) phosphate buffer solution. 42
Figure 3. 10 Chronoamperometric results with different concentration of hypochlorite in 0.1 M, pH 7 phosphate buffer. 43
Figure 3. 11 FIA system coupled with Zensor ECD 100 electrochemical detector and SF 100 flow cell for FIA responses of hypochlorite and the calibration curve at the dimer-modified electrode (A). FIA responses of (a) hypochlorite (b) H2O2, (c) EtOH, (d) urea, (e) Cl–, (f) NO2–, (g) S2O42–, (h) CO32–, (i) NO3–, (j) hypochlorite, (k) ClO4–, (l) SO42–, (m) Cu2+, (n) Zn2+, (o) Co2+, (p) Fe2+, (q) saturated-O2, (r) Na+, (s) K+, (t) hypochlorite and (u) F– (B). FIA responses of 40 continuous injections of 1 mM hypochlorite (C). 44
Figure 3. 12 Flow rate and applied potential optimization for FIA detection of hypochlorite 45
Figure 3. 13 Detection of hypochlorite in swimming pool water. 46
Figure 3. 14 Detection hypochlorite in swimming pool water by standard DPD colorimetric method (A), Corresponding calibration plot (B). 47

Figure 4. 1 Schematic representation of fluorophenylboronate complex formation in pH 3 phosphate electrolyte for FIA detection of fluoride ion. 51
Figure 4. 2 Cyclic voltammetry response of bare SPCE (a), SPCE-APBAD (b) in 5 mM ferric cyanide solution and inset electrodimerization of 4-APBA in 0.1 M, HCl at SPCE (a’), SPCE* (b’). 53
Figure 4. 3 Electrodimerization (A) and Electropolymerization (B) of 4-APBA on AuSPE. 54
Figure 4. 4 SEM images of AuSPE (A), AuSPE-APBAD (B), AuSPE-PAPBA (C). 55
Figure 4. 5 UV absorption spectrum of bare AuSPE and AuSPE-APBAD (A), APBA monomer and polymer in water (B). 55
Figure 4. 6 XPS spectrum of SPCE*-APBAD (inset deconvoluted B-1S spectrum). 56
Figure 4. 7 Potentiometric detection of fluoride ion in 0.1 M, pH 3 phosphate electrolyte, Each spike contains 1 mM (a-b), 2mM (b-c) and 5mM (c-d) (inset- calibration graph). 57
Figure 4. 8 Cyclic voltammogram responses of SPCE*-APBAD under different concentrations of fluoride ion in 0.1 M, pH 3 phosphate electrolyte. 57
Figure 4. 9 DFT optimized geometries for APBAD and APBAD+Fluoride (blue colour:N, dark grey:C, grey:H, red:O, pink:B, sky blue:F). 59
Figure 4. 10 HOMO and LUMO molecular orbital diagram of APBAD and APBAD+Fluoride complex. 59
Figure 4. 11 The total electronic density diagram of APBAD and APBAD+Fluoride complex 60
Figure 4. 12 Proposed mechanism for FIA detection of fluoride ion. 60
Figure 4. 13 Detection of fluoride ion by FIA method at SPCE-APBAD (A), SPCE*-APBAD (B). 62
Figure 4. 14 Flow rate and potential optimization of FIA fluoride ion detection. 62
Figure 4. 15 Interference (A) and repeatability study (B) at SPCE*-APBAD by FIA. 63
Figure 4. 16 Fluoride ion detection in real samples by FIA drinking water (A), tap water (B), tooth paste (C). 65

Figure 5. 1 Cyclic voltammograms of SPCE*/APBAHCl and SPCE*/APBAPBS in 0.1 M, pH 7 PBS (A&B) and dashed line represents CV of SPCE*, Corresponding reblank CVs in 0.1 M, HCl (C&D). 71
Figure 5. 2 Cyclic voltammograms of SPCE*/APBAH3PO4 (A), SPCE*/APBAPBS pH6 (B), SPCE*/APBAPBS pH8 (C) in 0.1 M, HCl at a scan rate 100 mVs-1. 72
Figure 5. 3 Electrochemical reduction CV of SPCE* in N2 saturated 0.1 M, pH 7 PBS (A), Raman spectra for SPCE* and ERSPCE* (B). 73
Figure 5. 4 Cyclic voltammograms of SPCE*/APBAPBS, ERSPCE*/APBAPBS and OPSPCE/APBAPBS in 0.1 M, pH 7 PBS (A&B). 74
Figure 5. 5 Cyclic voltammogram of SPCE/APBAPBS in 0.1 M, pH 7 PBS at a scan rate 100 mVs-1. 75
Figure 5. 6 The optimized structure and HOMO-LUMO molecular orbital diagram of 4-APBA and 4-APBA+phosphate complex. 76
Figure 5. 7 Total electron density image of APBA and APBA+phosphate complex. 76
Figure 5. 8 CVs of PAPBA formation at various preanodization time (A) and phosphate concentration (C) in 0.1 M, pH 7 PBS, between -0.5 V and + 0.5 V at a scan rate 50 mV/s, Their corresponding current verses preanodization time plot (B) and current verses phosphate concentration plot (D). 78
Figure 5. 9 SEM images of polished SPCE (A&B) and SPCE*/PAPBAPBS modified electrode at different resolutions (C&D). 79
Figure 5. 10 SEM image of SPCE*/APBAHCl modified electrode. 80
Figure 5. 11 UV-visible spectra of APBA monomer and ethanol extract of PAPBA (A), XPS spectra of SPCE*/APBAPBS modified electrode, corresponding N1s resolved spectra (inset) (B). 81
Figure 5. 12 Cyclic voltammograms of SPCE*/3-APBAHCl and SPCE*/3-APBAPBS in 0.1 M, pH 7 PBS (A) and after medium exchange to 0.1 M, HCl (B). 82
Figure 5. 13 Cyclic voltammograms of the SPCE*/ APBAPBS in the absence/presence of 2 mM Fructose in 0.1 M, pH 7 PBS containing 5 mM Fe(CN)64–/3–(A), in the absence/presence of 1 mM Fluoride in 0.1 M, pH 3 PBS containing 5 mM Fe(CN)64–/3– (B), Electrocatalytic detection CVs of 2 mM hypochlorite and 1 mM NADH Cyclic voltammograms in 0.1 M, pH 7 PBS respectively (C&D), scan rate 50 mVs-1. 83

Figure 6. 1 Schematic representation of SPCE/ANBA modified electrode in presence and absence of phosphate. 87
Figure 6. 2 Cyclic voltammogram (A) and Square wave voltammogram (B) of SPCE/ANBA (a), SPCE-AN (b) without phosphate and SPCE/ANBA (c) with 100 mM Phosphate in 0.1 M, pH 7 Acetate electrolyte. 90
Figure 6. 3 ANBA oxidation on SPCE* and ERSPCE* in 0.1 M, pH 7 Acetate electrolyte. 90
Figure 6. 4 XPS spectrum of SPCE/AQBA-Pi complex electrode (inset deconvoluted P-2P, B-1S and C-1S spectrums). 91
Figure 6. 5 DFT optimized geometries and molecular orbital diagrams of ANBA and ANBA-Pi complex. 93
Figure 6. 6 Total electron density diagram of ANBA and ANBA-Pi. 93
Figure 6. 7 Relative AQ current change in different electrolyte media. 94
Figure 6. 8 Square wave voltammogram (A) of (a) SPCE, (b) SPCE/ANBA, SPCE/ANBA with (c) 10 µM, (d) 30 µM, (e) 50 µM, (f) 100 µM, (g) 500 µM, (h) 1 mM, (i) 5 mM, (j) 10 mM, (k) 50 mM, (l) 100 mM phosphate in 0.1 M HCl, Corresponding calibration plot (B) and Interference study (C) at SPCE/ANBA with 1 mM Pi/ various interferants. 95
Figure 6. 9 Real sample analysis of Pi in tap water and lake water. 97

List of Tables
Table 3. 1 Comparison of hypochlorite detection at different chemically modified electrode. 45
Table 3. 2 Recovery in swimming pool water. 47

Table 4. 1 Comparison of fluoride ion detection with other reported boronic acid modified electrodes. 64
Table 4. 2 Real sample fluoride ion detection recovery data. 66

Table 6. 1 Real sample analysis of Pi in tap and lake water. 96

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