本研究中我們主要聚焦在四種主題，皆是關於合成帶有azobenzene和coumarin分子之高效能光感應型polybenzoxazine。Polybenzoxazine(PBZs)是一種典型的的熱塑型高分子，不需要任何催化劑便可在加熱的環境下開環形成高分子。我們經由縮合反應成功地製備出帶有azobenzene和pyridine分子及coumarin和pyrene分子地benzoxazine單體，azobenzene和coumarin分子扮演著以下角色：(i) 於光異構作用下azobenzene可以在平面的trans結構和非平面的cis結構間交互轉換，而coumarin分子可以經由〔2π＋2π〕形式做環加成反應，(ii) 並且做為一種催化劑可以加速benzoxazine開環且降低所需的curing溫度。之後，我們利用benzoxazinec單體可以和Zn(ClO4)2、MWCNTs或是SWCNTs間有非共價鍵作用力(金屬-配位鍵、分子間氫鍵和π-π堆疊作用力)，這些複合材料有著很高的熱穩定性和玻璃轉移溫度(Tg)，從DSC、TGA和DMA分析中得知因為交聯密度提升所致，並且從TEM結果得知可以有效地分散奈米碳管(CNTs)。

In this study, we focus on four major subjects which based on synthesis of high performance/photoresponsive polybenzoxazines containing azobenzene and coumarin units. As known Polybenzoxazines (PBZs) are class of thermosetting polymers which could be synthesized through thermally activated ring-opening polymerization of benzoxazine monomers in the absence of catalyst. In this study, we have successfully prepared benzoxazine monomers that features azobenzene, pyridine, coumarin, and pyrene units through the condensation reaction. The azobenzene, pyridine and coumarin units in the benzoxazine play the following roles: (i) allowing the photoisomerization between the planar trans and the nonplanar cis form for azobenzene units; formation the photodimerization of coumarin units through [2π+2π] cycloaddition and (ii) serving as catalyst to accelerate the ring-opening polymerization benzoxazine monomer to reduce the higher curing temperature. Then, we used the noncovalent interactions (such as, metal-ligand bonding mode, intermolecular hydrogen-bonding and π-π stacking interactions) between benzoxazine monomers and Zn(ClO4)2, MWCNTs and SWCNTs. Those hybrid materials exhibit higher thermal stability and glass transition temperatures (Tg) due to the increasing physical crosslinking density according to DSC, TGA, and DMA analyses, and well uniformly dispersed carbon nanotubes (CNTs) according to TEM images.

Pages
論文審定書 i
Acknowledgements ii
Abstract (in Chinese) iii
Abstract (in English) iv
Outline of Contents v
List of Schemes ix
List of Figures x

Chapter 1 Introduction 1
1.1 Overview on Benzoxazines and Polybenzoxazines 1
1.2 Effect of Intra and Intermolecular Hydrogen Bonding on Low Surface Free-Energy Materials 3
1.3 Catalytic Effect on the Ring-Opening Polymerization of 1,3-Benzoxazine monomer 4
1.4 Photoresponsive Groups 5
1.5 Carbon Nanotubes (CNTs) 6
1.6 Motivation 8
1.7 References 9

Chapter 2 Azopyridine-functionalized benzoxazine with Zn(ClO4)2 form high-performance polybenzoxazine stabilized through metal-ligand coordination 13
2.1 Background 13
2.2 Experimental 15
2.2.1 Materials 15
2.2.2 Synthesis of Azopy-OH 16
2.2.3 Synthesis of Azopy-BZ 16
2.2.4 Measurements 17
2.3 Results and Discussion 18
2.3.1 Synthesis of Azopy-BZ through Mannich reaction of Azopy-OH with aniline and paraformaldehyde 18
2.3.2 Thermal Polymerization of Azopy-OH 20
2.3.3 Photoisomerization of azopyridine chromophore in Azopy-BZ 21
2.3.4 Thermal Polymerization of Azopy-BZ blended with Zn(ClO4)2 22
2.4 Summery 26
2.5 References 27

Chapter 3 Supramolecular functionalized polybenzoxazines from azobenzene carboxylic acid/azobenzene pyridine complexes: synthesis, surface properties, and specific interactions 46
3.1 Background 46
3.2 Experimental 49
3.2.1 Materials 49
3.2.2 Measurements 49
3.2.3 Preparation of 4-(4-Hydroxphenylazo)benzoic acid (Azo-COOH) 50
3.2.4 Synthesis of Azo-COOH BZ 51
3.2.5 Preparation of Azo-COOH BZ/Azopy-BZ Complexes 52
3.3 Results and Discussion 52
3.3.1 Synthesis of Azo-COOH BZ through Mannich reaction of Azo-COOH with aniline and paraformaldehyde 52
3.3.2 Thermal Polymerization of Azo-COOH BZ 53
3.3.3 Photoisomerization of azobenzene chromophore in Azo-COOH BZ 55
3.3.4 Supramolecular azobenzene-containing benzoxazine complexes stabilized through carboxylic acid-pyridine hydrogen bonds 56
3.4 Summery 58
3.5 References 59

Chapter 4 High Performance Bifunctional Polybenzoxazine Nanocomposites from Photo-Induced Crosslinking Coumarin and Single-Walled Carbon Nanotube Stabilized through Non-Covalent Bonding Interactions 77
4.1 Background 77
4.2 Experimental 80
4.2.1 Materials 80
4.2.2 Synthesis of Pyrene-1-amine (Py-NH2) 80
4.2.3 Synthesis of 4-Methyl-7-hydroxycoumarin (Coumarin-OH) 81
4.2.4 Synthesis of (Coumarin-Py BZ) 81
4.2.5 Photodimerization of Coumarin-Py benzoxazine 82
4.2.6 Measurements 82
4.3 Results and Discussion 83
4.3.1 Preparation of Coumarin-Py BZ monomer 83
4.3.2 Thermal Polymerization of Coumarin-Py BZ 85
4.3.3 Photodimerization through [2π+2π] cycloaddition coumarin moiety 86
4.3.4 The preparation and thermal properties of coumarin-Py BZ/SWCNT nanocomposites 89
4.3.5 Thermal properties of di-coumarin-Py BZ/SWCNT nanocomposites 90
4.4 Summery 92
4.5 References 94

Chapter 5 Multifunctional Polybenzoxazine Nanocomposites Containing Photoresponsive Azobenzene Units, Catalytic Carboxylic Acid Groups, and Pyrene Units Capable Dispersing Carbon Nanotubes 122
5.1 Background 122
5.2 Experimental 125
5.2.1 Materials 125
5.2.2 Synthesis of Pyren-1-amine (Py-NH2) 125
5.2.3 Synthesis of 4-(4-Hydroxyphenylazo) benzoic acid (Azo-COOH-Py BZ) 126
5.2.4 Synthesis of Azo-COOH-Py BZ 127
5.2.5 Photoisomerization of Azo-COOH-Py BZ 127
5.2.6 Preparation of poly(AzoPy-COOH BZ) films 128
5.2.7 Azo-COOH-Py BZ/CNT Nanocomposites 128
5.2.8 Measurements 128
5.3 Results and Discussion 129
5.3.1 Synthesis of Azo-COOH-Py BZ Monomer 129
5.3.2 Thermal Curing Behavior of Azo-COOH-Py BZ Monomer 131
5.3.3 Photoisomerization of Azobenzene Chromophore in Azo-COOH-Py BZ Monomer 133
5.3.4 Poly(Azo-COOH-Py BZ)/CNTs Nanocomposites 134
5.4 Summery 138
5.5 References 140

Chapter 6 Conclusions 160

Resume 162

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