Thermo- and photo-driven crystalline molecular switches comprising pseudorotaxanes

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研究生：	蔡雅晴
論文名稱：	Thermo- and photo-driven crystalline molecular switches comprising pseudorotaxanes
指導教授：	堀江正樹
口試委員:	蘇安仲游進陽
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2013
畢業學年度：	101
語文別：	英文
論文頁數：	113
中文關鍵詞：	Supermolecule 、Molecular switch 、Thermo-responsive 、Photoresponsive 、Pseudorotaxane
相關次數：	點閱：2 下載：0
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This thesis describes the thermo- and photo-driven molecular switches comprising ferrocene-containing pseudorotaxanes in the solid state. Chapter 1 presents an overview of supermolecular chemistry as well as the purpose of this project. Chapter 2 describes the reversible mechanical deformations of the single crystals of the pseudorotaxanes caused by a combination of temperature control and light-irradiation. Laser irradiation to the ferrocenyl group of the pseudorotaxane induces molecular structural changes in the crystals: it triggers a crystal-to-crystal thermal phase transition deforming the crystal shape at 124 ºC; it causes rapid and reversible expansion of the crystal at room temperature. In addition, the local laser irradiation to a part of the single crystal enables selective transport of micro-particles. Chapter 3 describes the preparation and morphological studies of the thermally responsive pseudorotaxane films. The thin films of the pseudorotaxane molecule can be prepared on a glass or SiO2 substrates by a solution casting method, which affords the polycrystalline films without dissociation of the pseudorotaxane molecule. Obtained films are characterized by X-ray diffraction, differential scanning calorimetry (DSC), polarized optical microscopy, and grazing incident wide-angle X-ray scattering (GIWAXS) measurement with temperature control. The pseudorotaxane film on the substrate exhibits the reorganization of the molecule to give a large crystal face with 50-100 μm on heating, followed by the reversible solid-to-solid thermal phase transition on heating and cooling. GIWAXS analysis can conduce to the molecular alignment of the pseudorotaxane in the film; the pseudorotaxane adopts edge-on orientation, in which one-side of oligo-ethylene glycol group -(CH2CH2O)n- of the dibenzocrown ether molecule in the pseudorotaxane lies on the substrate, probably due to the molecule-surface interaction and formation of the bulky interlocked structure. Chapter 4 described the synthesis and characterization of a new pseudorotaxane composed of 4,4’,5,5’-tetrabromodibenzo[24]crown-8 ether as a ring molecule and ferrocene-containing ammonium cation as an axle molecules. The optical properties of the pseudorotaxane are observed and related to the molecular alignment in the single crystal state. Chapter 5 presents the conclusions of the project and gives forecast of this research. Finally chapter 6 presents the experimental conditions.

Abstract    I
Table of contents    III
Chapter 1     Introduction and aim    1
1    Introduction of supermolecular chemistry    1
1.1    Supermolecules    1
1.2    Supermolecular chemistry    2
1.3    Shape of supermolecules    4
2    Molecular switches and machines    6
2.1    Artificial molecular switches (AMSs)    8
2.2    Artificial molecular machines (AMMs)    11
3    Movement of molecules in solid state: metal–organic frameworks (MOFs)    13
4    Conversion of molecular motion into macroscopic motion    17
4.1 Thermo-induced movement of molecules    17
4.2 Photo-induced movement of matters caused by molecular motions    21
5    Application of rotaxanes    25
6    Aim of the work    29
Chapter 2     Photo-induced mechanical motion of pseudorotaxane crystals        31
1    Introduction    31
2    Photo-induced mechanical motion of single crystal of pseudorotaxane    34
3    Transportation of micro-particles    40
4    Multi stimuli-responsive pseudorotaxane crystal    43
5    Conclusion    49
Chapter 3     Preparation and characterization of pseudorotaxane film    50
1    Introduction    50
2    Preparation of film    55
3    Characterization of film    56
4    Thermal and optical properties    64
5    Morphological characterization    67
6    Conclusion    74
Chapter 4     Synthesis and characterization of pseudorotaxane composed of crown ether with ferrocene-containing axle molecule    76
1    Introduction    76
2    Synthesis of pseudorotaxanes    77
3    X-ray single crystallography    82
4    Optical properties    84
5    Thermal properties    87
6    Conclusion    91
Chapter 5     Conclusion    92
Chapter 6     Experimental section    94
1    General methods    94
2    Birefringence measurement    95
3    Optical setup with laser light    99
4    Preparation of p-xylyl(ferrocenylmethyl)ammonium hexafluorophosphate, [F-H]+(PF6)-    102
5    Preparation of pseudorotaxane: [F•DB24C8](PF6)    105
6    Preparation of pseudorotaxane: [F•DB24C8-Br4](PF6)    107
7    X-ray single crystallography    109
References    111

                                

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