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研究生： 程紹奇
Cheng, Shao-Chi
論文名稱： 含偶氮苯超分子晶體之光熱誘導機械運動
Stimuli-induced Mechanical Motions of Azobenzene Containing Pseudorotaxane Crystals
指導教授： 堀江正樹
Masaki, Horie
口試委員: 蘇安仲
Su, An-Chung
游進陽
Yu, Chin-Yang
周鶴修
Chou, Ho-Hsiu
劉振良
Liu, Cheng-Liang
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： 2019
畢業學年度： 107
語文別： 英文
論文頁數： 237
中文關鍵詞： 超分子 、晶體 、偶氮苯 、光熱誘導
外文關鍵詞： pseudorotaxane, crystal, azobenzene, photo-responsive
相關次數： 點閱：2  下載：0 
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    • 本研究探討含偶氮苯超分子晶體之光熱致異構化機械性質及動力學
    　　第二章描述超分子晶體的合成與透過單晶繞射探討它們的分子排列。其中，環上具有溴分子取代基或是偶氮苯末端接上甲基之超分子擁有特殊的彎曲反式偶氮苯結構。以外，此類超分子晶體的異構化性質依據分子間/內的作用力來決定，例如晶體1與2在偶氮苯上有很強的分子間作用力，此一特性將導致異構化的困難性；對於偶氮苯末端取代基稍長的晶體3和4，雖然擁有和1一樣的晶體系統，卻失去原本偶氮苯之間的分子作用力，取而代之的是軸環本身的分子內作用力。因此，此一超分子晶體將具備更多異構化的彈性空間；然而在偶氮苯末端擁有很長乙基的晶體5則是因為分子的立體障礙導致分子之間沒有存在任何作用力，卻也提供很大的異構化特性。
    在第三章我們對於晶體1-8做了一系列紫外/可見光的照射實驗。重複且交替的紫外/可見光照射導致晶體不同方向的彎曲，且沒有明顯的衰退。在可見光的照射下，晶體可以在0.3秒內完成彎曲的行為，比其他含偶氮苯化合物的相關文獻還快速。此外，偶氮苯的順反轉化率也由UV-vis和1H NMR光譜來判斷。
    第四章闡述含二茂鐵超分子晶體在照射聚焦445奈米雷射光後產生的光致機械能效應。當使用強度低(4 mW)的445奈米雷射，晶體3和4產生蜷曲的機械行為。如果提高雷射強度到12 mW，更明顯的機械性質如翻轉、跳躍甚至輸送行為可以被觀察到。此章節亦探討光致機械能所產生的力，晶體6可以承受極高的雷射強度並提供將近9600倍自己晶體本身的重量值。這些超分子的異構化動力學可藉由一級反應速率公式推導出速率常數k以及異構化活化能Ea，相較於軸分子1，超分子1擁有更快的恢復率以及較低的活化能。
    第五章提及此類含偶氮苯超分子晶體的總結論和未來展望，相關的實驗細節收錄在第六章。

    This study investigates the dynamic thermally and photoinduced mechanical motions and kinetics of photoisomerization of azobenzene containing pseudorotaxane crystals.
    In Chapter 2, the synthesis and characterization of new pseudorotaxane crystals and their molecular packing structures observed in single-crystal X-ray crystallography are described. X-ray crystallography shows pseudorotaxanes with a methylazobenzene group and a dibromophenylene ring in the cyclic component to exhibit unique twisting of the trans-azobenzene groups at torsion angles. In addition, the isomerization mobility of crystals was predicted based on their intra- and intermolecular  interaction. single crystals of 1 and 2 have strong π-π stacking interaction between aromatic ring A-B’ and A’-B, which potentially increase difficulty in trans-to-cis isomerization of azobenzene groups. With the slight elongation in axle molecule of single crystals of 3 and 4, the crystal system remains the same as 1 yet there is only intramolecular π-π interaction between aromatic ring B-C. In this case, azobenzene groups are relatively flexible without any interaction. However, a single crystal of 5 having long axle length changes the molecular alignment as well as crystal system to monoclinic. There is no molecular interaction existing in 5, which may provide high mobility for cis-trans isomerization of azobenzene groups.
    In Chapter 3, the reversible laser-induced bending motions of pseudorotaxane crystals 1-8 using 360 nm/445 nm lasers are described. Repeated alternating laser irradiation of the crystals at 360 and 445 nm produces bending in opposite directions, with no evidence of decay. Under 445-nm irradiation, bending takes place within 0.3 seconds, which is much faster than that reported in the literature for organic azobenzene derivative crystals. Since the changes observed in the crystal shape are related to isomerization of the azobenzene groups under laser irradiation, the rate of photoisomerization conversion of the azobenzene groups are evaluated by UV-vis absorption spectra and 1H NMR spectra, separately.
    In Chapter 4, mechanical switching of crystals of ferrocene-containing pseudorotaxanes controlled by focused 445 nm laser light are investigated. Slim photomechanical motions such as thermal expansion and curling are observed in crystals of 3 and 4 under low power intensity (4 mW). When irradiated to the same crystals using 445 nm at 12 mW, obvious photosalient effect like flipping, jumping and transporting can be achieved. For 6 with larger ring molecule, the crystal eventually exhibits jumping motions at extremely high power intensity (43 mW). The forces produced by photo-induced molecular motions were also measured under variables of condition. Under same but weak laser intensity of 445 nm, a single crystal of 3 produced the most force compared to 1 and 6. However, 6 can endure under extremely high laser intensity (ca. 43 mW), which provide the most force among three crystals (ca. 9600 times crystal itself). On the other hand, kinetics of these [2]pseudorotaxanes are also discussed. Rate constant (k) and activation energy (Ea) can be derived from plot assuming first-order reaction for isomerization of azobenzene groups. Pseudorotaxane 1 showed the fastest recovery rate and lower Ea compared with 1-Axle. On the other hand, Tol-1 without ferrocenyl group has lower Ea yet slower recovery rate than 1.
    In Chapter 5, summary and future prospective regarding of these azobenzene containing pseudorotaxane crystals series is described.
    In Chapter 6, the experimental procedures and analysis data, such as 1H NMR, 13C NMR, elemental analysis, FD and ESI mass spectra are summarized.

    Table of contents Abstract I Table of contents III Acknowledgement VI Summary of pseudorotaxane complexes 1 Chapter 1 Introduction and aim 4 1.1 Supramolecular chemistry 4 1.2 Molecular machines 5 1.2.1 Mechanically interlocked molecular architectures 5 1.2.2 Molecular switches and motors 7 1.2.3 Switchable molecular shuttles 9 1.2.4 Recent molecular machines and switches 12 1.3 Azobenzene and its derivatives 15 1.3.1 Mechanism of cis-trans isomerization of an azobenzene 15 1.3.2 Kinetics of cis-trans isomerization of an azobenzene in solution 17 1.4 Molecular motions in solid state 19 1.4.1 Crystalline molecular machine 19 1.4.2 Mechanical motions of an azobenzene-containing component in solid state 22 1.4.3 Mechanical motions of an azobenzene-containing component in crystal state 24 1.5 Aim of the work 27 Chapter 2 Synthesis and characterization of an azobenzene containing pseudorotaxanes 31 2.1 Introduction 31 2.2 Synthesis of azobenzene-containing pseudorotaxanes 34 2.3 Optimization of synthesis 43 2.3.1 Optimization of azobenzene precursors via Mills reaction 43 2.3.2 Optimization of azobenzylamine synthesis 45 2.4 X-ray crystallography of crystals 47 2.4.1 Analogy of crystallographic data among crystals 47 2.4.2 Miller indices of crystals 54 2.4.3 Intra- and intermolecular interactions of crystals 56 2.5 Conclusion 63 Chapter 3 Rapid and reversible photo-induced bending of pseudorotaxane crystals 65 3.1 Introduction 65 3.2 Photoisomerization of [2]pseudorotaxane crystals 69 3.2.1 Bending motions of crystals induced by alternating 360-nm and 445-nm laser 69 3.2.2 Bending directions of crystals based on their molecular alignments and isomerization ability of azobenzene groups 72 3.2.3 Photoisomerization conversion of azobenzene groups determined by UV-vis absorption spectroscopy 75 3.2.4 Photoisomerization conversion of azobenzene groups determined by 1H NMR spectroscopy 77 3.3 Conclusion 88 Chapter 4 Photomechanical effect and kinetics of ferrocene and azobenzene containing pseudorotaxane crystals 91 4.1 Introduction 91 4.2 Photosalient effect of ferrocene and azobenzene containing pseudorotaxane crystals 96 4.3 Photoinduced force measurements of ferrocene and azobenzene containing pseudorotaxane crystals 101 4.4 Kinetics of cis-to-trans isomerization of azobenzene containing pseudorotaxanes in solution state 105 4.5 Conclusion 111 Chapter 5 Suggestions and future prospective 113 Chapter 6 Experimental section 116 6.1 General methods 116 6.2 Experimental methods 118 6.3 Synthesis of 1,1’-ferrocenedicarboxaldehyde 126 6.4 Synthesis of N-(ferrocenylmethyl)-4-(phenylazo)benzene methanamine hydrohexafluorophosphate, [(Fc-Azo)·H]+(PF6)- 128 6.5 Synthesis of N-(ferrocenylmethyl)-4-(tolylazo)benzene methanamine hydrohexafluorophosphate, [(Fc-Methylazo)·H]+(PF6)- 134 6.6 Synthesis of N-(ferrocenylmethyl)-4-(4-ethylphenylazo)benzene methanamine hydrohexafluorophosphate, [(Fc-Ethylazo)·H]+(PF6)- 143 6.7 Synthesis of N-(ferrocenylmethyl)-4-(methoxylazo)benzene methanamine hydrohexafluorophosphate, [(Fc-Methoxylazo)·H]+(PF6)- 149 6.8 Synthesis of N-(ferrocenylmethyl)-4-(hexoxylazo)benzene methanamine hydrohexafluorophosphate, [(Fc-Hexoxylazo)·H]+(PF6)- 155 6.9 Synthesis of N-(ferrocenylmethyl)-4-(4-hydroxyphenylazo)benzene methanamine hydrohexafluorophosphate, [(Fc-Hydroxylazo)·H]+(PF6)- 161 6.10 Synthesis of 1,1’-bis[(E)-4-(phenylazo)benzene methanamine hydrohexafluorophosphate, [(Fc-2N)·2H]2+(2PF6)2- 171 6.11 Synthesis of DB24C8 derivatives 173 6.12 Synthesis of pseudorotaxane crystals 179 6.13 X-ray single crystallography 209 References 231 Lists of publications 236 List of presentations 236 Honor/Achievements 237 Exchange experiences 237

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