臺灣博碩士論文加值系統

本論文主要是研究二苯胺－鄰胺基苯甲酸共聚導電性高分子的電化學合成機構、電化學、光電化學行為及其導電度的研究。論文可分作三部分，首先將針對二苯胺－鄰胺基苯甲酸共聚導電性高分子的電化學共聚合進行研究，接著探討胺－鄰胺基苯甲酸共聚導電性高分子的光電化學行為。
二苯胺－鄰胺基苯甲酸共聚導電性高分子的電化學合成是在4 M H2SO4水溶液中，以循環伏安法在0.0 V ∼0.7 V的電位區間，掃瞄速率為100 mV/s，以不同的二苯胺/鄰胺基苯甲酸進料比進行聚合。並以相同的條件對二苯胺進行電化學聚合。相對於純二苯胺聚合的循環伏安圖，共聚合的循環伏安掃瞄的電流有抑制的現象。利用聚合時的陰極電流的電荷總量代表其高分子的量，以非線性迴歸可以推導出高分子聚合的速率式：QG = k [DPA]2.0 [AA]-0.2 Cn1.2。高分子的組成的鑑定則是利用X射線光電子光譜所得到。由所得知的高分子組成，利用Fineman-Ross及Kelen-Tüdös可以計算出各單體的反應性比(reactivity ratio)。其中二苯胺的反應性比為10.02，而鄰胺基苯甲酸的反應性比則為0.02。
在電化學共聚反應的過程中，使用紫外光－可見光光譜以便對二苯胺－鄰胺基苯甲酸共聚進行光電化學的研究。電化學的合成是在2 M H2SO4的水溶液下，以定電位的方式，在鍍有indium tin oxide的導電玻璃上進行。在此單體的濃度比在電化學分析實驗中來得低的原因是為了使吸收度在紫外光－可見光光譜可以分析的範圍。在共聚合的過程中可以看到二種陽離子自由基，分別代表苯胺型式的（anilinium type）及二苯胺型式的（N,N’-diphenylbenzidine type）陽離子自由基。由紫外光－可見光光譜所得到資訊可以發現，二苯胺型式的陽離子自由基的吸收峰位置和反應時溶液中的鄰胺基苯甲酸的濃度有關係，也因此得知由於鄰胺基苯甲酸單元併入高分子結構中所造成的氧化狀態的改變。而由傅利葉轉換紅外線光譜分析亦可得知鄰胺基苯甲酸併入高分子結構中。此外，亦由熱重分析實驗中，可以到因鄰胺基苯甲酸的併入高分子主鏈，使得高分子熱穩定性得到提昇。

Conducting copolymers of diphenylamine (DPA) and anthranilic acid (AA) were synthesized by electrochemical and chemical oxidative polymerization methods. Cyclic voltammetry was used for concomitant synthesis and electrochemical characterization of the copolymers. In situ UV-Visible spectroelectrochemical studies were performed to identify the intermediates generated during the electrochemical copolymerization. Copolymers of DPA and AA were synthesized for various DPA feed ratios in 4 M H2SO4 aqueous solution using K2S2O8 as oxidized agent. The synthesized copolymers were characterized for composition of the monomeric units, structure, and thermal properties through X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA).
Electrochemical copolymerization of diphenylamine with anthranilic acid was performed in aqueous 4 M H2SO4 solution for different feed ratios of DPA using cyclic voltammetry at a scan rate of 100 mV/s. The copolymer films were grown for different number of cycles, Cn, and molar feed ratios of comonomers. Electrochemical homopolymerization of DPA was also carried out under identical conditions and compared. The cyclic voltammograms (CVs) recorded for the copolymerization revealed that the peak potentials and peak current values are different from those of homopolymerization of DPA. The peak current was found to be suppressed for copolymerization on increasing the molar feed ratio of AA in comparison with homopolymerization of DPA. A growth equation for the deposition of copolymer film was established correlating to concentrations of DPA and AA and Cn as QG = k [DPA]2.0 [AA]-0.2 Cn1.2 by utilizing the charge associated for film deposition. XPS results clearly indicates the presence of increasing proportion of AA units in the copolymer with increase in the molar ratio of AA in the feed. The compositions of the two monomer units in the copolymer determined by X-ray photoelectron spectroscopy were used to determine the reactivity ratios of DPA ad AA by using Fineman-Ross and Kelen-Tüdös methods. DPA was found to have higher reactivity ratio (10.02) than AA (0.02).
The electrochemical behaviors of the copolymer films were studied by recording the CVs of copolymer films in monomer free background electrolyte (4 M H2SO4). The CV patterns of the stabilized copolymer films showed similarity to the CV patterns obtained in copolymerization signifying the deposition of copolymer during copolymerization. The linear relation obtained between square root of scan rate and the peak current for the copolymer films indicates the diffusion controlled behavior of the films.
In situ UV-Visible spectroelectrochemical studies were carried out on the polymerization of diphenylamine (DPA) and copolymerization of DPA with anthranilic acid (AA). Electropolymerization was performed in aqueous 2 M H2SO4 by applying a constant potential (0.80 V) on indium tin oxide (ITO) coated glass electrode. The concentrations of the monomers were kept lower than that used for electrochemical studies for the purpose of recording the UV-Visible spectrum with suitable absorption intensity. Spectral characteristics were followed for various feed ratios of the comonomers (DPA and AA) at different polymerization time. Two types of cation radicals corresponding to anilinium type and N,N’-diphenylbenzidine type (DPB+•) could be identified for the electropolymerization with mixture of DPA and AA, respectively. UV-Visible spectra recorded for copolymerization inform that the peak position corresponding to DPB+• showed clear dependence on AA concentration in the feed, signifying the changes in the overall oxidation states of the polymer as a result of incorporation of AA units in the copolymer.
The FTIR spectral analysis of the copolymer reveals the incorporation of AA units into the polymer backbone during polymerization. The presence of a band at 1650 cm-1 in FTIR spectra of the copolymers corresponding to the —C=O group of AA units and the improvement in thermal stability of the copolymer as observed from TGA results clearly support the incorporation of AA units in the copolymer.
Abstract ii
中文摘要 v
Symbols and Abbreviations vii
Contents xii
List of Figures xv
List of Schemes xviii
List of Tables xix
Chapter 1 Introduction 1
1-1 Conducting polymer 1
1-1-1 Development 2
1-1-2 Classification 3
1-1-3 Conducting mechanism 4
1-1-4 Applications 6
1-1-4-1 Photoconductivity 6
1-1-4-2 Electrochromic display 7
1-1-4-3 Electroluminescent display devices 8
1-1-4-4 Light emitting electrochemical cell (LEC) 9
1-1-4-5 Solid-state rechargeable batteries 10
1-1-4-6 Electrochemical supercapacitors 11
1-2 Synthesis of conducting polymer 13
1-2-1 Chemical method 13
1-2-2 Electrochemical method 15
1-2-3 Other methods 15
1-3 Polyaniline and its derivatives 17
1-3-1 Polymerization of aniline 18
1-3-2 Processability 22
1-3-3 Electrochemistry 24
1-3-4 Polyaniline derivatives 25
1-3-4-1 Substituted polyanilines 25
1-3-4-2 Sulfonated polyanilines 26
1-3-4-3 Other soluble conducting PANI derivatives 30
1-3-5 Determination of intermediates 30
1-4 Research motivation 33
Chapter 2 Electrocopolymerization of diphenylamine and anthranilic acid 46
2-1 Introduction 46
2-2 Experimental 49
2-2-1 Chemicals 49
2-2-2 Electrochemical copolymerization/homopolymerization. 49
2-2-3 Electrochemical behavior of copolymer/homopolymer films 50
2-2-4 X-ray Photoelectron Spectroscopy 50
2-3 Results and discussion 51
2-3-1 Electrochemical copolymerization/homopolymerization 51
2-3-2 Deducing the Growth Equation 54
2-3-3 XPS analysis 57
2-3-4 Copolymer composition and reactivity ratios 59
2-4 Conclusion 63
Chapter 3 Spectroelectrochemical study on copolymerization of diphenylamine and anthranilic acid 78
3-1 Introduction 78
3-2 Experimental 82
3-2-1 Chemicals 82
3-2-2 Spectroelectrochemical analysis 82
3-2-3 Synthesis of polymer/copolymer 83
3-2-4 Thermal analysis 83
3-2-5 Infrared Spectroscopy 83
3-3 Results and discussion 84
3-4 Conclusion 90
Chapter 4 Overall Conclusion 99
Appendix 102
A. Derivation of the copolymer composition equation 102
B. Determination of sequence length 105
References 107
Publication List 121
Conference Paper 121
Curriculum Vitae 122

封面
Acknowledgement
Abstract
中文摘要
Symbols and Abbreviations
Contents
List of Figures
List of Schemes
List of Tables
Chapter 1 Introduction
1-1 Conducting polymer
1-1-1 Development
1-1-2 Classification
1-1-3 Conducting mechanism
1-1-4 Applications
1-1-4-1 Photoconductivity
1-1-4-2 Electrochromic display
1-1-4-3 Electroluminescent display devices
1-1-4-4 Light emitting electrochemical cell (LBC)
1-1-4-5 Solid-state rechargeable batteries
1-1-4-6 Electrochemical supercapacitors
1-2 Synthesis of conducting polymer
1-2-1 Chemical method
1-2-2 Electrochemical method
1-2-3 Other methods
1-3 Polyaniline and its derivatives
1-3-1 Polymerization of aniline
1-3-2 Processability
1-3-3 Electrochemistry
1-3-4 Polyaniline derivatives
1-3-4-1 Substituted polyanilines
1-3-4-2 Sulfonated polyanilines
1-3-4-3 Other soluble conducting PANI derivatives
1-3-5 Determination of intermediates
1-4 Research motivation
Chapter 2 Electrocopolymerization of diphenylamine and anthranilic acid
2-1 Introduction
2-2 Experimental
Chemicals
2-2-2 Electrochemical copolymerization/homopolymeriztion
2-2-3 Electrochemical behavior of copolymer/homopolymer films
2-2-4 X-ray Photoelectron Spectroscopy
2-3 Results and discussion
2-3-1 Electrochemical coplymerization/homopolymerization
2-3-2 deducing the Growth Equaton
2-3-3 XPS analysis
2-3-4 Copolymer composition and reactivity ratios
2-4 Conclusion
Chapter 3 Spectroelectrochemical study on copolymerization of diphenylamine and anthranilic acid
3-1 introduction
3-2 Experimental
3-2-1 Chemicals
3-2-2 Spectroelectrochemical analysis
3-2-3 Synthesis of polymer/copolymer
3-2-4 Thermal analysis
3-2-5 Infrared Spectroscopy
3-3 Results and discussion
3-4 Conclusion
Chapter 4 Overall conclusion
Appendix
A Derivation of the copolymer comosition equation
B Determination of sequence length
References
Publicaion List
Conference Paper
Curriculum Vitae

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