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研究生:曾璟薇
研究生(外文):Jing Ching-Wei Tseng
論文名稱:含酯基與羧酸基之碳烯金屬錯合物
論文名稱(外文):Ester- and Carboxylate- functionalized N-Heterocyclic Carbene Complexes: Liquid Crystals and Photoluminescence.
指導教授:林志彪林志彪引用關係
指導教授(外文):Ivan J. B. Lin
學位類別:博士
校院名稱:國立東華大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2016
畢業學年度:104
論文頁數:370
中文關鍵詞:離子性液晶咪唑鹽金屬碳烯發光材料
外文關鍵詞:Ionic Liquid crystalimidazolium saltMetal N-heterocyclic carbeneLuminescence materials
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本論文以酯基或羧酸酯基之官能化含氮雜環為主軸,涵蓋了離子性液晶 (ionic liquid crystals,ILCs) 與金屬碳烯化合物 (N-Heterocyclic Carbene complexes(NHCs)),進行一系列具有液晶性質材料的應用研究。利用調整咪唑基上碳鏈端或酯基端的碳鏈長度可有效調控結構之不對稱性,間接造成液晶相範圍的大幅轉變。酯基咪唑鹽類兼具熱致型及液致型液晶特性,在有機溶劑中能形成LC凝膠。分析發現,此化合物在溶液中隨濃度漸增,分子會由層狀聚集成微胞,並分別形成Lamellar 與Cubic mesophase。進一步在含酯基之咪唑鹽類中引入鋰鹽,可得到具方向性之離子傳導物質。此外,摻雜鋰鹽之混合物亦有成膠性質,具有出色的離子導電率。延伸咪唑鹽連接基位置之側鏈長度可有效降低融點溫度,得到一系列室溫型液晶。將其應用為固相微萃取塗覆材料,利用塗材進入液晶相後軟度增加可幫助吸附,澄清相亂度變高以幫助脫附的特性,可有效提升偵測效果。此外,這些咪唑鹽均表現出不錯的抗微生物活性。含酯基之金屬碳烯化合物兼具液晶與發光特性,藉由銀碳烯化合物置換金屬,可得到陰離子為AgBr2-之金碳烯化合物。有趣的是,調整碳鏈長度可調控化合物的放光顏色,推測是由於碳鏈長度的改變影響Energy Gap所導致。利用醯酸基咪唑鹽作為起始物,可藉由改變兩性銀碳烯化合物之碳鏈長度或配位之金屬陽離子大小(Li+, Na+, and K+)輕易調控其液晶性質,碳鏈較短或陽離子較小時,會有立方體液晶的形成;當碳鏈增長或陽離子較大時,則轉變為層狀結構。
This thesis describes the synthesis and characterization of ester- and carboxylate- functionalized imidazolium salts and their corresponding N-Heterocyclic carbene (NHC) complexes. Ester-functionalized imidazolium salts show liquid crystalline properties and form LC gels in several organic solvents. When doping with Li salts, these salts exhibit excellent ionic conductivities in the LC and LC gel states. Extending the side chain length of the imidazolium salts on the linker of ester group will give rise to room-temperature ILCs. These imidazolium salts are also found to enhance the extraction of concentration in the sample preparation of solid-phase microextraction (SPME). Furthermore, these imidazolium salts exhibit antimicrobial activity. Ester functionalized NHC complexes of [Ag/Au(NHC)2][AgBr2] type display mesophase and photoluminescence properties. When incorporating a small cation of Li+ to carboxylate-functionalized AgI- NHCs to bridge two intramolecular carboxylate NHCs, cubic phase is observed. On the other hand, with larger cations of Na+ or K+ SmA phase is found. Furthermore, Ag complexes with one Li+/Na+/K+ carboxylated and one carboxylic acid NHCs only show SmA phase.
Chapter 1. General Introduction 3
Chapter 2. Thermotropic Ionic liquid crystals of Ester-functionalized imidazolium salts. 9
2.1 Abstract 9
2.2 Introduction 11
2.3. Results and discussion 13
2.3.1 Synthesis 13
2.3.2. Crystal structures 15
2.3.3. General LC properties 21
2.3.4. Effect of the N-alkyl chains 27
2.3.5. Effect of Functional Group 31
2.3.6. Effect of the Counterion 33
2.4. Conclusion 39
2.5. Experimental 41
Chapter 3. The Roles of Betaine – Ester Analogues of 1-N-alkyl-3-N’-methyl Imidazolium Salts: As Amphotropic Ionic Liquid Crystals and Organogelators 73
3.1 Abstract 73
3.2 Introduction 75
3.3 Results and discussion 77
3.3.1 Synthesis 77
3.3.2 Crystal structures 79
3.3.3 Liquid-crystalline properties 83
3.3.4 Lyotropic liquid crystal (LLC) phases in CHCl3 91
3.3.5 Gelation study 95
3.3.6 Preparation of silver nanoparticles (Ag-NPs). 103
3.4 Conclusion 107
3.5 Experimental 109
Chapter 4. Mesophase Properties and Gel Formation of LiBr Doped Ester-functionalized Imidazolium Salts. 121
4.1 Abstract 121
4.2 Introduction 123
4.3 Results and discussion 125
4.3.1 Liquid-crystalline properties of the mixtures 125
4.3.2 Gelation study of the mixture 135
4.3.3 Ionic Conductivity 137
4.4 Conclusion 143
4.5 Experimental 145
Chapter 5. Applications of Imidazolium-based Room-temperature Ionic Liquid Crystals. 147
5.1 Abstract 147
5.2 Introduction 149
5.3 Results and discussion 151
5.3.1. Synthesis and characterization 151
5.3.2. Crystal structures 153
5.3.3. Thermtropic liquid crystal properties 157
5.3.4. Powder X-ray study 165
5.3.5. FT-IR study 169
5.4 Imidazolium-Based Ionic Liquid Crystals SPME Fibers 171
5.4.1. Method 171
5.4.2. Result and discussion 173
5.5 Antibacterial activity. 191
5.6 Conclusion 193
5.7 Experimental 195
Chapter 6. Ester Functionalization Induced and Chain Length Tuned Liquid Crystals and Photoluminescence of Gold (I) N-heterocyclic Carbene Complexes. 221
6.1. Abstract 221
6.2. Introduction 223
6.3. Results and Discussion 225
6.3.1 Synthesis 225
6.3.2 Disproportionation of double salts bis-NHC AuI complexes 227
6.3.3 X-ray Crystallography 231
6.3.4. Thermotropic liquid crystal properties 237
6.3.5 Photophysical Study 249
6.4. Conclusion 259
6.5. Experimental 261
Chapter 7. Metallomesogens Based on Zwitterionic and Ionic N-Heterocyclic Carbene AgI Complexes 283
7.1 Abstract 283
7.2 Introduction 285
7.3 Reults and Discussion 287
7.3.1 Synthesis and characterization 287
7.3.2 Crystal structures 289
7.3.3 Thermotropic liquid-crystalline properties. 295
7.3.4 Powder X-ray study 301
7.3.5 Variable-temperature FT-IR studies 309
7.3.6 Ionic Conductivity Studies 311
7.3.7 Antibacterial Studies 314
7.4 Conclusion 317
7.5 Experimental Section 319
Chapter 8. Reference 331

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