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研究生：	邱逸閎 Chiu, Yi-Hong
論文名稱：	自組裝功能性單體及高分子之合成及特性研究 Study on the Synthesis and Characterization of Self-Assembled Functional Monomers and Polymers
指導教授：	劉瑞祥 Liu, Jui-Hsiang
學位類別：	博士 Doctor
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2010
畢業學年度：	98
語文別：	英文
論文頁數：	129
中文關鍵詞：	自組裝、奈米銀線、環糊精、包容錯合物、活性自由基聚合、兩嵌段式共聚物
外文關鍵詞：	elf-assembly, silver nanowire, cyclodextrin, inclusion complexes, atom transfer radical polymerization, diblock copolymer
相關次數：	點閱：103 下載：4
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自組裝技術在製備奈米材料上，因具備了成本低、可適用於廣泛材料上等優勢，而引起廣大的注意。本研究為了瞭解不同化學結構對自組裝行為的影響，設計且合成了一系列新穎性的單體及高分子，在結構中分別導入了具有光學活性、光敏感性或發光性官能基。而研究中所合成的化合物均以1H-NMR, 13C-NMR 和FTIR鑑定其化學結構，並利用DSC, TGA, UV-vis和POM測量其熱性質、光學性質和光異構化反應，最後以POM, SEM, TEM和AFM觀察自組裝所形成之微結構。

本研究依所製備超分子之特性不同而分為四個部分，在第一部分利用兩性分子以逆微胞技術製備銀奈米粒子，所製備的奈米銀粒子可藉由界面活性劑長碳鏈段間的凡得瓦力作用，在適當條件下，可自組裝誘導出中空銀奈米管的生成，由於奈米級銀粒子具有低熔點之特性，故自組裝的銀奈米管可於500℃下燒結得到銀奈米線，並完全移除有機模板。本實驗以octanoic acid 和甲基丙烯酸甲酯作為界面活性劑及有機相，硝酸銀和硼氫化鈉為銀奈米粒子的前驅物和還原劑，藉由改變水和界面活性劑的莫耳比 (w)、硝酸銀水溶液的濃度及不同的有機相，探討不同變因對銀奈米粒子自組裝行為的影響。實驗中所製備之奈米銀粒子經UV-vis、XRD及EDXA鑑定；而自組裝奈米管之微結構可藉由TEM、SEM及AFM量測。

光學活性化合物一般會表現出特有之立體排列及特殊之分子間引力關係，因而形成在立體結構上具有非常特殊之物性。故在研究的第二部分，合成出一個新穎性光學活性單體，在末端導入膽固醇基團，並將此單體與β-環糊精形成包容錯合物。經1H-NMR分析結果顯示，平均約有一到二個β-環糊精分子與光學活性單體形成包容錯合物，可誘導出螺旋結構。此自組裝包容錯合物的形成可以藉由SEM以及TEM來鑑定其微結構。此自組裝包容錯合物具有單體的性質，因此可利用benzoyl peroxide作為光起始劑將其聚合。經聚合後的自組裝的超分子，經POM和圓光色差光譜儀(circular dichrosim, CD)證實其高秩序性排列及其螺旋結構的存在。本研究提供了一個簡易製備具螺旋結構之高分子的方法。甚至將聚合後包容錯合物超分子當中的β-環糊精去除後，經POM和CD證實失去β-環糊精的高分子，可藉由高分子鏈的纏繞以及側鏈膽固醇基團間的作用力維持其螺旋結構。

在研究的第三部分，嘗試合成具有共軛鏈段的發光基團衍生物 (phenyl- [1,3,4]-oxadiazolyl group) ，並將此單體與β-環糊精形成包容錯合物。經1H-NMR分析結果顯示，平均約有一到二個β-環糊精分子與此單體形成包容錯合物，並可誘導出高次序性的纖維狀結構，此自組裝之包容錯合物在POM下展現具有異方性排列特性。而此自組裝之包容錯合物在螢光(photoluminescence, PL)光譜下，展現了光致誘導螢光增強的效應，推測應是β-環糊精可與發光基團產生分子間的作用力，進而抑制了發光基團將能量以震動或轉動的方式釋放，而有效的將能量以放光的形式釋出。另外，環糊精腔體的疏水性，也減少發光基團與極性溶液發生外部轉換，而造成螢光強度減弱的機會。

在論文的最後一個部分，嘗試合成具有光敏感性偶氮苯衍生物單體，並利用活性自由基聚合法製備兩嵌段式共聚物，以甲基丙烯酸甲酯做為第一個鏈段；而第二鏈段則是由光敏性偶氮苯衍生物高分子所組成，此兩嵌段式共聚物(PMMA- b-PAzoMA)在濃度為2 wt %的混合溶液中(THF/H2O mixture of 1:2)，可自組裝形成奈米微球，若進一步將此結構經紫外光照射後，可觀察到奈米棒的生成，此構形上的變化主要是因為偶氮苯衍生物鏈段，經紫外光照射後，會誘導光異構化反應的發生，此時不僅僅是偶氮苯分子化學結構發生變化，也改變了分子的偶極矩和極性，因而影響了自組裝構形在溶液中的改變。奈米微球和奈米棒的構形變化可藉由紫外光與可見光的交替照射，為一可逆的變化過程。

Self-assembly has become a very effective and promising approach to synthesize a wide range of novel nanoscale materials. In our research work, a series of novel monomers and polymers containing chiral, photosensitive, chromophore groups were designed and synthesized to investigate the structure-property relation to self- assembled supramolecules. The chemical structures of synthesized compounds were identified using 1H-NMR, 13C-NMR and FTIR. The thermal, optical, photo-induced properties of these compounds were analyzed using DSC, TGA, UV-vis and POM. The morphologies of self-assembled supramolecules were analyzed using POM, SEM, TEM and AFM.

This dissertation consists of four parts. In the first part, we provide a novel method for the fabrication of silver nanowires under controlled conditions. Silver nanoparticles were synthesized using a surfactant of octanoic acid via a reverse micelle technique. Hollow nanotubes were formed under various controlled conditions through self-assembly of surfactant clusters of reversed micelles containing silver nanoparticles. These organized nanotubes were used as a structure-directing template for the preparation of silver nanowires. Self-assembled nanotube construction and the cross section of the nanotubes were investigated using SEM and TEM. Further sintering treatment at 500 oC burned away the organic compounds and left silver nanowires. The construction of the nanowires was confirmed using SEM, XRD, and EDXA.

In the second part, in order to investigate chiral effect on formation of inclusion complex, two kinds of novel chiral monomer end-capped with a cholesteryl group and achiral monomer end-capped with a phenyl-[1,3,4]oxadiazolyl group were synthesized. As results, the chiral monomer containing a cholesteryl group [cholesteryl-4-(6-acryloyloxyhexyloxy) benzoate (CAHB)] threaded with β-cyclo- dextrin was synthesized in order to induce the formation of a helical polymer. 1H-NMR studies revealed that one or two cyclodextrin molecules were threaded onto the synthesized chiral monomer, leading to the formation of a helical construction of self-assembled inclusion complexes. The monomeric self-assembled inclusion complex was further polymerized using benzoyl peroxide as a photoinitiator. Both the highly ordered alignment and the helical structure of self-assembled supramolecules were confirmed using polarized optical microscopy and circular dichroism spectroscopy, respectively.

In the third part, achiral monomer containing a chromophore group (phenyl-[1,3,4]-oxadiazolyl group) threaded with one or two β-cyclodextrin was synthesized, leading to the formation of fibrous construction of self-assembled inclusion complexes. The highly ordered alignment of self-assembled supramolecules was confirmed using polarized optical microscopy. The self-assembled inclusion complex revealed enhancement of photo-induced fluorescence due to significant interaction between the phenyl-[1,3,4]-oxadiazolyl moiety of monomer and β-cyclodextrins.

In the final part, a novel monomer, ethyl 4-[4-(11-methacryloyloxyundecyloxy) phenyl azobenzoyl-oxyl] benzoate, containing a photoisomerizable N=N group was synthesized. The monomer with methyl methacrylate was further diblock copolymerized. Amphiphilic diblock copolymer poly(methyl methacrylate-block -ethyl 4-[4-(11-methacryloyloxy-undecyloxy) phenyl azobenzoyl-oxyl] benzoate (PMMA-b-PAzoMA) was synthesized using atom transfer radical polymerization. The reverse micelles with spherical construction were obtained with 2 wt % of the diblock copolymer in a THF/H2O mixture of 1:2. Under alternating UV and visible light illumination, reversible changes of micellar structure between sphere and rod-like particles took place as a result of the reversible E-Z photoisomerization of azobenzene segments in PMMA-b-PAzoMA. Due to upon UV irradiation, the hydrophilicity of PAzoMA segment may be increased (trans-form into cis-form) leading to the aggregation of nanoparticles. The increase of solubility of PAzoMA in water may increase the mobility of the PAzoMA segment moving to the surface of the rod-like nanoparticle. Microphase separation of the amphiphilic diblock copolymer in thin films was achieved through thermal and solvent aligning methods. The microphases of the annealed thin films were investigated using AFM and SEM analyses.

Abstract………………………………………I
中文摘要………………………………………III
Acknowledgments………………………………………V
Table of Contents………………………………………VII
List of Figures………………………………………XIII
List of Schemes………………………………………XIX
List of Tables………………………………………XXI

Chapter 1. General Introduction……………………………………….1
1-1 INTRODUCTION OF NANOMATERIAL	1
1-2 MICROFABRICATION	1
1-3 RESEARCH MOTIVATIONS	3

Chapter 2. Review And Theoretical Background …………………….7
2-1 SELF-ASSEMBLY	7
2-1.1 Definition of self-assembly	7
2-1.2 Self-assembly of amphiphilic molecules	7
2-1.3 Surfactants: packing-directed self-assembly	8
2-2 SYNTHESIS OF SILVER NANOPARTICLES	9
2-2-1 Synthesis of silver nanoparticles by reverse micelle method	10
2-2.2 Introduction of reverse micelle[12]	10
2-2.3 Reaction dynamics in reverse micelle	11
2-2.4 Synthesis of silver nanoparticles by surfactant reverse micelles	12
2-2.5 Self-assembly of silver nanoparticles	14
2-3 AMPHIPHILIC BLOCK POLYMER	16
2-3.1 Amphiphilic block copolymers self-assembly in solution	18
2-3.2 Photoresponsive block copolymers	19
2-3.3 Synthesis of amphiphilic diblock copolymer	24
2-4 CYCLODEXTRIN	29
2-4.1 Properties of cyclodextrins	30
2-4.2 CD inclusion complexes	30
2-4.3 Fabrication of inclusion complexes	32
2-4.4 Self-assembly of CD inclusion complexes	33
2-4.5 Application of CD inclusion complexes	35

Chapter 3.	The Fabrication of Polycrystalline Silver Nanowires via Self-Assembled Nanotubes at Controlled Temperature …………….37
3-1 INTRODUCTION	37
3-2 EXPERIMENTAL SECTION	39
3-2.1 Instruments	39
3-2.2 Preparation of silver nanoparticles and formation of silver nanotubes	40
3-3 RESULTS AND DISCUSSION	41
3-3.1 Effect of the factor w on the formation of silver nanotubes	41
3-3.2 Effect of the organic phase on the formation of silver nanotubes	44
3-3.3 Effect of the concentration on the formation of silver nanaotubes	47
3-3.4 The construction of silver nanotubes	48
3-3.5 The thermal properties of silver nanoparticles	50
3-3.6 The existence of silver nanoparticles	52
3-3.7 Mechanism for the formation of silver nanowires	54
3-4 SUMMARY	56

Chapter 4. Fabrication and Characterization of Self-Assembled β-Cyclodextrin Threaded Monomers and Induced Helical Polymer…………………………………………………………………………..57
4-1 INTRODUCTION	57
4-2 EXPERIMENTAL SECTION	58
4-2.1 Instruments	58
4-2.2 Monomer and inclusion complex preparation	59
4-2.3 Polymerization of self-assembled monomers	62
4-3 RESULTS AND DISCUSSION	62
4-3.1 Synthesis of monomers threaded with β-cyclodextrin	62
4-3.2 Polymerization of β-cyclodextrin threaded monomers	69
4-4 SUMMARY	71

Chapter 5. Polymerization and Characterization of Self-Assembled β-Cyclodextrin-Threaded Chiral Monomers……………………..	73
5-1 INTRODUCTION	73
5-2 EXPERIMENTAL SECTION	74
5-2.1 Instruments	74
5-2.2 Monomer and inclusion complex preparation	75
5-2.3 Polymerization of the self-assembled monomers	77
5-2.4 Removal of β-cyclodextrin from the inclusion complex polymer	77
5-3 RESULTS AND DISCUSSION	78
5-3.1 Solvent effect on the self-assembly of the inclusion complexes	78
5-3.2 Characterization of polymerized self-assembled inclusion complexes	79
5-3.3 Removal of the threaded β-cyclodextrin from pendant groups of polymers	82
5-4 SUMMARY	84

Chapter 6. The Spectrophotometric Study of a Fluorescence- Enhanced Inclusion Complex Threaded with β-Cyclodextrin: Synthesis and Characterization……………………………………….85
6-1 INTRODUCTION	85
6-2 EXPERIMENTAL SECTION	87
6-2.1 Instruments	87
6-2.2 Monomer preparation	87
6-2.3 Preparation of monomer threaded with β-cyclodextrin	89
6-3 RESULTS AND DISCUSSION	90
6-3.1 Synthesis of inclusion complex	90
6-3.2 Spectrophotometric Analysis	91
6-3.3 Supramolecular Properties	95
6-3.4 Polymerization of the Self-Assembled Inclusion Complex	97
6-4 SUMMARY	97

Chapter 7.	Behaviors of Self-Assembled Diblock Copolymer with Pendant Photosensitive Azobenzene Segments ……………………...99
7-1 INTRODUCTION	99
7-2EXPERIMENTAL SECTION	101
7-2.1 Instruments	101
7-2.2 Materials	101
7-2.3Monomer preparation	101
7-2.4 Synthesis of diblock copolymers	103
7-2.5 Self-assembly of diblock copolymer PMMA-b-PAzoMA	104
7-3 RESULTS AND DISCUSSION	105
7-3.1 Synthesis of diblock copolymer PMMA-b-PAzoMA	105
7-3.2 Self-assembly of diblock copolymer PMMA-b-PAzoMA in solvent	108
7-3.3 Thermal annealing of diblock copolymer	111
7-3.4 Solvent annealing of diblock copolymer films	113
7-4 SUMMARY	115

Chapter 8. Conclusions	…………………………………………...…117

References……………………………………………………………..119

Appendix……………………………………………………………...127
                                    

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