Systematically Control of Color-tunable Aggregation-Induced Emission (AIE) Indolizine core and bioapplication
- 주제(키워드) 형광체 , 인돌리진 , 응집유도발광
- 주제(DDC) 547
- 발행기관 아주대학교
- 지도교수 김은하
- 발행년도 2022
- 학위수여년월 2022. 2
- 학위명 박사
- 학과 및 전공 일반대학원 분자과학기술학과
- 실제URI http://www.dcollection.net/handler/ajou/000000031830
- 본문언어 영어
- 저작권 아주대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
Fluorescent materials, the spontaneous light emission of irradiated materials, have some features of high sensitivity, technical simplicity, and fast response time for attractive and versatile tools such as drug discovery, cellular imaging, environmental analysis, electronic devices, and various medical applications. Despite of its widespread application in various fields, only few are researching novel fluorescent scaffolds that are harsh and tedious work. Many researchers are focusing on understanding and manipulating the conventional fluorophores. But still, it is needed the systematic change and design of fluorophore that can emphasize the utility and applicability of fluorescent materials. In the whole research, we focused on developing the new indolizine based fluorescent molecular frame to understand and to control systematically that can change its photophysical property like a kaleidoscope, called Kaleidolizine. The unique features of Kaleidolizine give a great potential for developing imaging techniques: 1) predictable photophysical property based on computational calculation covering full visible-color range 2) strong fluorescence emission in solid state that can consider lots of possibilities to apply on devices, and 3) great potential for detection of analytes in biological systems.
more목차
Chapter I. Introduction 1
1.1. Organic fluorescent material 4
1.1.1. Fluorescein 5
1.1.2. Boron difluoride dipyrromethene (BODIPY) 9
1.1.3. Cyanine 11
1.1.4. Rhodamine 13
1.2. Aggregation-caused quenching (ACQ) & Aggregation-induced emission (AIE) 14
1.2.1. Aggregation-caused quenching (ACQ) 15
1.2.2. Aggregation-Induced emission (AIE) 16
a. Hexaphenylsilole (HPS) 17
b. Tetraphenylethylene (TPE) 18
c. Triphenylamine (TPA) 19
1.3. Objectives of a thesis 19
1.4. Reference 21
Chapter II. Design and development of color-tunable kaleidoscopic indolizine scaffold 29
Abstract 30
2.1 Introduction 31
2.2 Experimental section 32
2.2.1 Materials and compound characterization 32
2.2.2 Solution state photophysical property measurement 33
2.2.3 Solid state photophysical property measurement 33
2.2.4 Quantum mechanical calculations 33
2.3 Result and discussion 34
2.3.1 Synthesis and analysis of molecular structure 34
2.3.2 Photophysical properties of KIz compounds 36
2.4 Conclusion 40
2.5 References 42
Chapter III. The color-tunable Aggregation-Induced Emission (AIE) fluorescent scaffold based on indolizine scaffold 46
Abstract 47
3.1 Introduction 48
3.2 Experimental section 49
3.2.1 Materials and compound characterization 49
3.2.2 Solution state photophysical property measurement 50
3.2.3 Solid state photophysical property measurement 50
3.2.4 Quantum mechanical calculations 51
3.2.5 Photophysical Property Study Depending on Viscosity 51
3.2.6 Crystal Study 51
3.2.7 Fluorogenic Mitochondrial Live Cell Imaging with TPP-KIz 52
3.2.8. Cytotoxicity Test 52
3.3 Result and discussion 53
3.3.1 Aggregation-Induced Emission effect of Kaleidolizine 53
3.3.2 Aggregation-Induced Emission property of Kaleidolizine 55
3.3.3 Molecular structure analysis 56
3.3.4 Computational analysis of Kaleidolizine 57
3.3.5 The fluorescence mechanism of Kaleidolizine 59
3.4 Conclusions 62
3.5 References 64
Chapter IV. Tetrazine modified potential click chemistry Turn-on/off bioimaging probe kaleidolizine 69
Abstract 70
4.1 Introduction 71
4.2 Experimental section 74
4.2.1 Materials and compound characterization 74
4.2.2 Photophysical property measurement (Solution and Solid) 75
4.2.3 Quantum mechanical calculations 76
4.2.4 AIE Experiment 76
4.2.5 Live cell imaging experiment 76
4.3 Result and discussion 77
4.3.1 Molecular design and chemical analysis 77
4.3.2 Positional effect of tetrazine on indolizine core skeleton 78
4.3.3 Color-tuning of KIz-tetrazine 81
4.3.4 Study of the mechanism of action of KIz-tetrazine 83
4.3.5 Bioimaging application KIzTz 87
4.4 Conclusions 89
4.5 References 91
Chapter V. Systematically controllable Photodynamic therapy agent Kaleidolizine 98
Abstract 99
5.1 Introduction 100
5.2 Experimental section 101
5.2.1. Materials and compound characterization 101
5.2.2. Photophysical property measurement 102
5.2.3. Quantum mechanical calculations 102
5.2.4. Aggregation-induced emission property experiment 103
5.2.5. ROS generation experiment 103
5.2.6. Photodynamic Therapy with TPP-KIz 103
5.2.7. Cytotoxicity Test 104
5.2.8. Western-blot analysis 104
5.3. Result and discussion 105
5.3.1. Photodynamic therapy of KIz 105
5.3.2. Controlling Singlet-Triplet Energy Gap (△EST) 107
5.3.3. Molecular design and synthesis 109
5.3.4. Analysis of PDT effect 111
5.4. Conclusion 114
5.5. References 115
Chapter VI. Conclusion & Perspectives 118
6.1 Conclusion 119
6.2 Perspectives 120
Appendix 121
