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Effect of Alkyl Chain Length in Pyridinium-based Ionic Liquids on Electrochemical Behavior of Carbon Ionic Liquid Electrode And Spectrofluorimetric Determination of Doxycycline in Honey Based on the Plasmonic Interaction between its Europium Complex and Silver Nanoparticl

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MSc. Thesis in Analytical Chemistry

Effect of Alkyl Chain Length in Pyridinium-based Ionic Liquids on Electrochemical Behavior of Carbon Ionic Liquid Electrode

And

Spectrofluorimetric Determination of Doxycycline in Honey Based on the Plasmonic Interaction between its Europium Complex and Silver Nanoparticles

ABSTRACT

In this study, six pyridinium-based ionic liquids were synthesized in order to use them as binder in fabrication of carbon ionic liquid electrode (CILE). The physical properties such as wetting angle, resistance and electrochemical behavior of ionic liquids (ILs) were studied. We have shown that increasing the hydrocarbon chain length increase hydrophobic character of electrode surface as well as resistance and peak separation (ΔEp) and decrease π- π interaction between ILs and graphite particles so that the electric current in the system reduced.

A new spectrofluorimetric method is described for the determination of doxycycline (DOXY), based on plasmonic interaction between silver nanoparticles (AgNPs) and lanthanide luminescence. The procedure has been demonstrated to be sensitive, selective, accurate and precise simple and rapid, and has been successfully applied for the determination of DOXY in honey sample with minimal sample pretreatment. Recovery percent for the real sample was 93.21-107.05% under the optimum conditions. The calibration graph was linear over the range of 0.18 –3.30 µg mL−1 with good reproducibility, 1.35-3.43 %. (n=5) and the limit of detection was 0.013 µg mL−1.

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List of Contents

CHAPTER ONE INTRODUCTION.. 1

1.1. Effect of Alkyl Chain Length in Pyridinium-based Ionic Liquids on Electrochemical Behavior of Carbon Ionic Liquid Electrode. 2

1.1.1. Carbon Electrodes. 2

1.1.1.1. Carbon Paste Electrodes. 3

1.1.2 Ionic Liquid. 4

1.1.2.1 Application of ILs as Electrolyte in Electrochemistry. 4

1.1.2.2. Ionic Liquids as Electrode Modifier 5

1.1.2.3. ILs as Binder for Construction of Carbon Paste Electrodes. 6

1.1.3. Carbon Ionic Liquid Electrodes. 6

1.1.4. Contact Angle and Wetting Properties. 7

1.1.5. Four-Point Probe Measurement of Semiconductor Sheet Resistance. 9

1.2. Spectrofluorimetric Determination of Doxy-cycline in Honey Based on the Plasmonic Interaction between its Europium Complex and Silver Nanoparticles. 12

1.2.1. Lanthanide-Sensitized Fluorescence. 12

1.2.2. Optical Properties of Metal Nanoparticles. 13

1.2.3. Metal-Enhanced Fluorescence (MEF) 14

1.2.4. Surface Plasmon-Enhanced Luminescence. 15

1.2.4.1.Lanthanide Complex Enhanced Luminescence by Silver Nanoparticles. 15

1.2.5. Doxycycline hyclate. 17

CHAPTER TWO LITERATURE REVIEW… 20

2.1. Effect of Alkyl Chain Length in Pyridinium-based Ionic Liquids on Electrochemical Behavior of Carbon Ionic Liquid Electrode. 21

2.2. Spectrofluorimetric Determination of Doxycycline in Honey Based on the Plasmonic Interaction between its Europium Complex and Silver Nanoparticles. 24

2.2.1. Lanthanide Complexes as Fluorescent Probes. 24

2.2.2. Enhanced Fuorescence by Silver Nanomaterials. 28

2.2.3. Determination of Doxycycline. 28

2.2.3. Objective. 29

CHAPTER THREE EXPERIMENTAL. 30

3.1. Effect of Alkyl Chain Length in Pyridinium-based Ionic Liquids on Electrochemical Behavior of Carbon Ionic Liquid Electrode. 31

3.1.1. Materials. 31

3.1.2. Apparatus and Software. 31

3.1.3. Synthesis of Ionic Liquids. 33

3.1.4. Electrode Preparation. 35

3.2. Spectrofluorimetric Determination of Doxy-cycline in Honey Based on the Plasmonic Interaction between its Europium Complex and Silver Nanoparticles. 36

3.2.1. Chemicals. 36

3.2.2. Apparatus. 36

3.2.3. Solutions. 37

3.2.4. General Analytical Procedure. 38

3.2.5. Assay Procedure for Honey Sample. 39

CHAPTER FOUR RESULTS AND DISCUSSION.. 40

4.1. Effect of Alkyl Chain Length in Pyridinium-based Ionic Liquids on Electrochemical Behavior of Carbon Ionic Liquid Electrode. 41

  1. 1. 1. Selection of Ionic Liquid. 41

  2. 1. 2. Physical Characteristics of Carbon Ionic Liquid Electrode (CILE) 42

4.1.2.1. Ohmic Resistance. 42

  1. 1. 2. 2. Electrode Wettability. 43

  2. 1. 3. Electrochemical Characteristics of CILEs. 45

4.1.3.1. Weight Ratio of IL/ Graphite and Background Current 45

  1. 1. 4 Electrochemical Behaviors. 50

4.1.4.1. Electrochemistry of Potassium hexacyanoferrate (K4Fe (CN)6) 50

4.1.4.2. Electrochemistry of Catechol 51

4.1.4. Conclusions. 53

4.2. Spectrofluorimetric Determination of Doxy-cycline in Honey Based on the Plasmonic Interaction between its Europium Complex and Silver Nanoparticles. 54

4.2.1. Spectral Characteristics. 54

4.2. pH and Buffer Types. 56

4.2.3. Effect of Europium Concentration. 58

4.2.4. Effect of AgNanoparticle Solution Volume. 59

4.2.5. Effect of Reagent Addition Order and Time Stability Test 60

4.2.5.1. Effect of Reaction Time. 60

4.2.6. Effect of Temperature. 62

4.2.7. Influence of Coexisting Substances. 63

4.2.8. Characteristics of the Analytical Method. 65

4.2.9. Determination of DOXY in Honey Sample. 68

4.2.10. Possible Mechanism.. 69

4.2.10. Conclusion. 70

References. 71

List of Tables

  Table                                                                                                        Page

Table 3.1. The results of NMR spectrum ……………………………………………………………… 35

Table 4.1.Some physical characteristics of the constructed carbon ionic liquid electrodes.   43

Table 4. 2. Result of cyclic voltammetry of 1.0 mM Fe(CN)64− in 0.1 M KCl. 49

Table 4.3.Results of cyclic voltammetry of 1.0 mM catechol in 0.1 M phosphate buffer (pH=7) on CILEs with differently-alkyl chain ILs…………………………………………………………………………………. 52

Table 4.4. Effect of the order of addition of reagents on the fluorescence intensity of DOXY-Eu(III)-AgNPs system at room temperature ………………………………………………………………………………. 61

Table 4.5. Effect of coexisting substances in the determination of DOXY.  ……………. 64

Table 4.6.The results of the measurements of ten blank solution. …………………………… 66

Table 4.7. Comparison of other methods for determination of Doxycycline…………….. 67

Table 4.8. Determination of DOXY in honey sample by the developed method. …….. 68

 

 

 

 

List of Figures

Figure…………………………………………………………………………………………..Page

Figure 1.1. Illustration of contact angles formed by liquid drops on a smooth homogeneous solid surface   8

Figure 1.2. Four-point probe measurement of semiconductor sheet resistance. 10

Figure 1.3. Chemical structure of tetracycline………………………………………………………. 17

Figure 1.4. Chemical structure of doxycycline hyclate. 19

Figure 3.1.Structure of n-alkylpyridinium-PF6. …………………………………………………….. 34

Figure 3.2. NMR spectrum of  octylpyridinium hexaflourophosphate (OPy-PF6) ionic liquid (H-NMR (250 MHz, CDCl3)) 34

Figure 3.3.UV–Vis spectrum of the solution of synthesized AgNPs……………………….. 38

Figure 4.1.Photographs of 1 µL drop of water on CILE surfaces. 44

Figure 4.2. Cyclic voltammograms of 0.1 M KCl (A), and 0.1 M phosphate buffer (pH=7), (B).    47

Figure 4.3. Cyclic voltammograms of 1.0 mM Fe(CN)64− in 0.1 M KCl (A) and 1.0 mM Catechol in 0.1 M phosphate buffer solution (pH=7.0) (B); at CILEs with different percentages of IL (hexylpyridinum-PF6) and graphite (IL/graphite, w/w)………………………………………………………………………………… 48

Figure 4.4. Cyclic voltammograms of 1.0 mM Fe(CN)64− in 0.1 M KCl on different CILE electrodes.       51

Figure 4.5. Absorption, (a) and fluorescence,(b) spectra of Eu(III), (1); DOXY, (2); DOXY–Eu(III), (3); DOXY–Eu(III)–AgNPs, (4) and AgNPs,(5). ……………………………………………………… 55

Figure 4.6. Effect of pH on the fluorescence intensity of DOXY- Eu(III)-AgNPs system at room temperature. ………………………………………………………………………………………………………………………. 56

Figure 4.7. Effect of buffer type on the fluorescence intensity of DOXY- Eu(III)-AgNPs system at room temperature. ……………………………………………………………………………………………………. 57

Figure 4.8.The effect of Tris-HCl buffer concentration on the fluorescence intensity of DOXY- Eu(III)-AgNPs system at room temperature. ……………………………………………………………………………… 58

Figure 4.9. Effect of europium concentration on the fluorescence intensity of DOXY- Eu(III)-AgNPs system at room temperature………………………………………………………………………………………….. 58

Figure 4.10. Effect of AgNPs solution volume on the fluorescence intensity of DOXY-Eu(III)-AgNPs system at room temperature. ………………………………………………………………………………………… 59

Figure 4.11.Effect of time on the fluorescence intensity of DOXY-Eu(III)-AgNPs system at room temperature……………………………………………………………………………………………………………………….. 62

Figure 4.12. Effect of temperature on the fluorescence intensity of DOXY-Eu(III)-AgNPs system.          63

Figure 4.13. Calibration curve. ………………………………………………………………………….. 65

List of Schemes

 

Scheme. 1.1. Obtaining doxycycline monohydrate and doxycycline hydrochloride from the way hyclate. 19

Scheme. 3.1. Four point probe setup. 32

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