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論文名稱 Title |
樟腦磺酸錯合對雙苯喹啉有機分子及高分子發光增益 Complexation of camphor sulfonic acid to affect the emission behavior of organic compound and polymer with quinoline moiety |
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系所名稱 Department |
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畢業學年期 Year, semester |
語文別 Language |
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學位類別 Degree |
頁數 Number of pages |
99 |
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研究生 Author |
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指導教授 Advisor |
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召集委員 Convenor |
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口試委員 Advisory Committee |
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口試日期 Date of Exam |
2010-07-14 |
繳交日期 Date of Submission |
2010-07-28 |
關鍵字 Keywords |
微胞、聚集誘導螢光 micelle, aggregation induced emissiom |
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統計 Statistics |
本論文已被瀏覽 5718 次,被下載 19 次 The thesis/dissertation has been browsed 5718 times, has been downloaded 19 times. |
中文摘要 |
螢光有機小分子及高分子在高濃度溶液態或固態時,會因為發色團靠近導致 π-π作用力而降低螢光量子效率,因此,發展出具有聚集時螢光強度增強之小分子或高 分子有其實用上之價值。本實驗室合成出具有旋轉自由度的雜環喹啉有機小分子(2,4-Diphenylquinoline, DPQ) 和 具 雜 環 喹 啉 側 基 之 螢 光 高 分 (poly(vinyl diphenylquinoline), PVQ),以探討其聚集誘導螢光增強效應 (aggregation induce emission, AIE)。為了論證文獻上所述抑制分子轉動(restriction of intramolecular rotation, RIR)是導致 AIE 的觀點,我們進一步在 DPQ 及 PVQ 內摻雜具有巨大基團的樟腦磺酸(camphor sulfonic acid, CSA),經由質子轉移作用使樟腦磺酸經由離子鍵鍵結於 DPQ 及 PVQ 的氮原子上,所得之 DPQ-CSA 及 PVQ-CSA 複合物具有較 DPQ 及 PVQ 更強之 AIE 現象,此結果可間接證實 RIR 為形成 AIE 現象的機構。延續研究 嵌 段 高 分 子 在 微 胞 方 面 之 AIE 應 用 , 所 選 用 的 嵌 段 高 分 子 是poly(styrene-block-tertbutylstyrene) (PS-b-PBS),經過合成方法合成出 PVQ-b-PBS,再混摻 CSA 而得到 PVQ-b-PBS-CSA,透過不同溶液的選擇,可以形成不同形貌的微胞,進而探討不同形貌的微胞對發光之影響,最後用原子力顯微鏡和穿透式電子顯微鏡來分析微胞的組成和外貌。 |
Abstract |
Many chromophoric organics and polymers are highly emissive in their dilute solutions but become weakly luminescent in the high concentration and solid film states due to the induced π−π interactions of the intimately-contact chromophores. Therefore, it is practically important to develop fluorescent organic and polymeric materials with enhanced emission in their aggregated states (so called aggregated-induced emission, AIE). In this study, organic compound 2,4-diphenylquinoline (DPQ) with inherent quinoline ring and polymeric poly(vinyl diphenylquinoline) (PVQ) with pendant quinoline group were prepared and their AIE-phenomena were characterized. To prove the reported point that restriction of intramolecular rotation (RIR) is the main cause for AIE effect, DPQ and PVQ were further incorporated with organic strong acid of camphorsulfonic acid (CSA). Through the favorable acid-base interaction between the sulfonic acid in CSA and the nitrogen atom of the quinoline ring in DPA (or CSA), ionic complex of DPQ-CSA (and PVQ-CSA) was easily prepared and their response toward AIE properties were studied. Through the enhanced RIR by the complexation of bulky CSA with the central quinoline ring, the resulting DPQ-CSA (and PVQ-CSA) complex was proved to have better AIE-effect compared to the pristine DPQ (and PVQ). RIR mechanism can be indirectly proved in this case. We study the AIE on micelle topics of the block copolymer. We choose the poly(styrene-block-tertbutylstyrene) (PS-b-PBS) as our block copolymer. To synthesize the PS-b-PBS, we can successfully get the new block copolymer PVQ-b-PBS. PVQ-b-PBS was similarly blended with the CSA. In the block copolymer micelles, choose the selective solvent to get the different micelles and observe the diverse on the luminescence. Finally, we analyzed compositions and conformations by atomic force microscopy (AFM) and transmission electron microscopy (TEM). |
目次 Table of Contents |
Outline of Contents Outline of Contents I List of Tables IV List of Schemes V List of Figures VI Abstract (in Chinese) X Abstract (in English XI Chapter 1 Introduction of the aggregation-caused quenching and aggregation-induced emission 1 1.1 Fluorescence and phosphorescence 1 1.2 Aggregate and excimer 2 1.3 Aggregates of organic molecules 4 1.4 Aggregation-induced emission phenomenon 5 1.4.1 Small-molecules siloes compounds 6 1.4.1.1 Viscochromism 12 1.4.1.2 Thermochromism 13 1.4.1.3 Piezochroism 15 1.4.1.4 Fluorescent decay dynamics 16 1.5 Applications of HPS 18 1.5.1 Chemical sensors 18 1.5.2 Detection of critical micelle concentration 20 1.6 New AIE systems 21 1.6.1 AIE-active silole-containing polymers 23 1.7 Motivation 25 1.8 References 28 Chapter 2 Studies on AIE properties of model compound DPQ, PVQ, DPQ-CSA and PVQ-CSA 31 2.1 Abstract 31 2.2 Introduction 32 2.3 Experimental 33 2.3.1 Materials 33 2.3.2 Instrumentations 35 2.4 Results and discussion 36 2.4.1 Primary spectral characterizations of different solution mixtures37 2.4.2 Molecular rotation from the cooling experiment 47 2.4.3 Lifetime measurements from the time-resolved fluorescence spectra 48 2.4.4 Comparison of molecular rotations of model DPQ and DPQ-CSA 51 2.5 Conclusions 54 2.6 References 55 Chapter 3 AIE effects of block copolymer of PVQ-PBS and its CSA-complexed PVQ(CSA)-PBS 58 3.1 Abstract 58 3.2 Introduction 59 3.3 Experimental 61 3.3.1 Materials 61 3.3.2 Instrumentations 61 3.3.3 Synthesis of poly((styrene)-block-tertbutylstyrene)62 3.3.4 Synthesis of poly((4-acetylstyrene)-block-4-tert-butylstyrene 62 3.3.5 Synthesis of poly((vinyl-diphenylquinoline)-block-4-tert-butylstyrene 63 3.4 Result and discussion 63 3.4.1 Synthesis and Characterization of block copolymers 63 3.4.2 AIE effect of PVQ-PBS and PVQ(CSA)-PBS 68 3.4.3 Morphology of block copolymer PVQ-PBS and PVQ(CSA)-PBS 73 3.4.4 Topography of PVQ(CSA)-PBS by TM-AFM 78 3.5 Conclusions 80 3.6 References 81 Chapter 4 Conclusions 83 List of Table Table 1-1 Fluorescence decay parameters of HPS solutions 17 Table 2-1 The appearance and the UV-vis absorption maxima of all samples in solvent/non-solvent mixtures 40 Table 2-2 PL quantum efficiency (ΦPL) measured from the solution mixtures and the solid samples41 Table 2-3 Data calculated from the fluorescent decay curves 51 Table 3-1 GPC test of block copolymer PS-b-PBS, PAS-b-PBS, and PVQ-b-PBS 67 Table 3-2 PL quantum efficiency (ΦPL) measured from the solution mixtures and the solid samples of PVQ-b-PBS and PVQ(CSA)-b-PBS 72 List of Schemes Scheme 1-1 Chemical structure of HPS and its synthetic route 8 Scheme 1-2 Schematic illustration of AIE mechanism 12 Scheme 1-3 Illustration of CMC detection in aqueous surfactant solution containing AIE-active amphiphile and structures of A 2 HPS and H2A2HPS2 21 Scheme 1-4 Synthesis of hyperbranched poly(2,5-silolylphenylene)s by homopolycyclotrimerization of diyne monomer 25 Scheme 3-1 Fabrication of the PVQ-b-PBS/CSA micelle 64 List of Figures Figure 1-1 The Jablonski diagram illustrates the general process involved during light absorption and emission of organic molecules 2 Figure 1-2 a) Excimer formation with the corresponding monomer and excimer emission ; and b) schematic diagrams for aggregate formation between fluorophore segments of inter- chain and intra-chain 4 Figure 1-3 Schematic representations of the H- and J- aggregates 5 Figure 1-4 Schematic illustration of ACQ and AIE 7 Figure 1-5 HPS in the acetonitrile/water mixtures containing different volume fractions of water; photographs taken under UV illumination 9 Figure 1-6 a) PL spectra of HPS in acetonitrile/water mixtures with different water fractions. b) Quantum yield (Φ F ) of HPS versus solvent composition of acetonitrile/water mixture 10 Figure 1-7 a) Absorption spectra of HPS in acetonitrile/water mixtures with different water fractions b),c) Size distributions of the nanoparticles of HPS 10 Figure 1-8 PL peak intensity of HPS versus composition of glycerol/methanol mixtures ; [HPS] = 10 -5 M 13 Figure 1-9 a) PL spectra of HPS in THF at different temperatures; [HPS] = 10 -5 M. b) NMR peaks of phenyl protons of HPS in dichloromethane-d2 at different temperatures 14 Figure 1-10 Switching the emission of HPS by a heating–cooling cycle. Photographs taken under UV illumination at a) room temperature (original solid powder) b) ~200 o C (melt liquid), and c) room temperature 14 Figure 1-11 Effect of externally applied pressure on the PL intensity of HPS films 16 Figure 1-12 Time-resolved fluorescence of HPS in DMF/water mixtures 17 Figure 1-13 Photos of the HPS spots on the TLC plates placed in the Petri dishes in the a) absence and b) presence of organic vapors. Photos in column c) were taken after the solvent had evaporated. All the photos were taken under UV illumination 19 Figure 1-14 Effects of acetone vapor on the PL spectra of the films of a) MPPS and b) HPS on quartz cell c) structure of MPPS 19 Figure 1-15 AIE-active of small phenylenes compounds 22 Figure 1-16 Chemical structures of pyran derivative and photographs of the nanoaggregates suspended in the THF/water mixtures with water contents 40, 90, and 99%, which emit green, yellow, and red lights, respectively, under illumination of a handheld UV lamp 23 Figure 1-17 Substituted polyacetylenes bearing silole pendant group 24 Figure 1-18 Photograph of polysilole in THF (10 mg/L, left) and polysilole nanoaggregates in water-THF mixture (90 : 10 by volume, 10 mg/L, right) under black light 24 Figure 1-19 The molecular structures of model compound (DPQ), polymer (PVQ) and block copolymer (PVQ-b-PBS) 27 Figure 2-1 1 H NMR spectra of DPQ in CDCl3 34 Figure 2-2 1 H NMR spectra of poly(4-acetylstyrene) (PAS) in CDCl 3 and of PVQ in CD2Cl2 35 Figure 2-3 Chemical structures of DPQ, PVQ, DPQ-CSA and PVQ-CSA 36 Figure 2-4 Solution (10 -4 M) UV absorption spectra of DPQ in the solvent mixtures of THF/water with various compositions 42 Figure 2-5 Solution (10 -4 M) UV absorption spectra of PVQ in the solvent mixtures of THF/water with various compositions 42 Figure 2-6 Solution (10 -4 M) UV absorption spectra of DPQ-CSA in the solvent mixtures of THF/hexane with various compositions 43 Figure 2-7 Solution (10 -4 M) UV absorption spectra of PVQ-CSA in the solvent mixtures of THF/hexane with various compositions 43 Figure 2-8 Dilute-solution (10 -4 M) emission spectra of a) DPQ and b) PVQ in the solvent mixtures of THF/hexane with various compositions 44 Figure 2-9 Dilute-solution (10 -4 M) emission spectra of a) DPQ-CSA and b) PVQ-CSA 45 Figure 2-10 Changes in the PL peak intensities of DPQ/PVQ and DPQ-CSA/PVQ-CSA with different poor solvent in poor solvent/good solvent mixtures 46 Figure 2-11 Integrated emission intensity from the solutions (10 -3 M) of DPQ, PVQ,DPQ-CSA and PVQ-CSA in chloroform at various temperatures 48 Figure 2-12 Fluorescence decay cures of the solid samples of DPQ. PVQ, DPQ-CSA ,PVQ-CSA 50 Figure 2-13 Simulated molecular structures of DPQ (right) and DPQ-CSA with minimum energy 53 Figure 2-14 The rotational energy barrier as the function of the rotational angle of the C2-phenyl rings in the model DPQ and DPQ-CSA 53 Figure 3-1 Representation of different copolymer architectures 59 Figure 3-2 Schematic representation of aggregation structures formed by block copolymers in solution 59 Figure 3-3 1 H NMR spectra of PS-b-PBS, PAS-b-PBS and PVQ-b-PBS in CDCl 3 65 Figure 3-4 FT-IR spectra of PS-b-PBS, PAS-b-PBS and PVQ-b-PBS in KBr 65 Figure 3-5 DSC scans of PS-b-PBS, PAS-b-PBS and PVQ-b-PBS 66 Figure 3-6 TGA scans of PS-b-PBS, PAS-b-PBS and PVQ-b-PBS 76 Figure 3-7 The UV-vis absorption spectra of a) PVQ-b-PBS and b) PVQ-b-PBS-CSA solution (10 -4 M) with mixed solvents 70 Figure 3-8 The PL emission spectra of a) PVQ-b-PBS and b) PVQ(CSA)-b-PBS solution (10 -4 M) with mixed solvents71 Figure 3-9 PVQ-b-PBS-CSA solutions in THF-hexane mixtures containing different volume fractions of Hexane; photographs taken under illumination of a UV lamp 71 Figure 3-10 Changes in the PL peak intensities of PVQ-PBS and PVQ(CSA)-PBS with different water fractions in the hexane/THF mixtures72 Figure 3-11 TEM images of the morphologies of the polymeric micelles prepared from 10 -5 M PVQ-b-PBS copolymers in THF/hexane (10:90 v%) a) cluster b) micelles75 Figure 3-12 TEM images of the morphologies of the polymeric micelles prepared from 10 -5 M PVQ-b-PBS-CSA copolymers in THF/hexane (10:90 v%) Cryo-TEM b) HF-2000 TEM 75 Figure 3-13 The size distribution of a)PVQ-b-PBS and b)PVQ(CSA)-b-PBS (concentration: 10 -5 M ,THF: hexane=10:90v%) 76 Figure 3-14 The phase lag varies in response to the mechanical properties of the sample surface 78 Figure 3-15 TM-AFM images a) topography image b) phase image 79 |
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