臺灣博碩士論文加值系統

Abstract
Organic compounds have been used extensively to construct photo luminescent materials, solar cells and chemosensors. Its significance can be attributed to easy synthesis, inexpensive staring materials, easy to tune photo physical properties and easy to link with other supporting materials. Fluorescence sensing is a process in which interaction between species is detected by change in the fluorescence intensity of system. Organic dyes are ideally suited to be used as probes for fluorescence sensing. This work therefore is focused on synthesis of organic fluorophores and their applications in bioimaging.
Chapter 1 describes importance of chemosensors, mechanism of signal transduction, and parameters needed to optimize in every sensor. How organic dyes been used as fluorescent sensors is further explained in following chapters.
Chapter 2 describes the synthesis of BODIPY based fluorescent probes (HCS and HCS2) for hypochlorite sensing. Both probes exhibited highly sensitive to hypochlorite over other reactive oxygen species and reactive nitrogen species. HCS and HCS2 are virtually non-fluorescent as photo-induced electron transfer taking place from sulfur to BODIPY. Hypochlorite induced oxidation of sulfur to sulfoxide which inhibited the PET process and generates turn-on fluorescence in a molecule. This mechanism was further supported by DFT calculations (B3LYP/6-31G (d)). Both probes are shown their ability to map external addition and internal secretion of hypochlorite in RAW 264.7 cells.
Chapter 3 reports design, synthesis and characterization of hydrogen peroxide sensing probes HP1 and HP2. Both probes exhibited highly sensitive to hydrogen peroxide over other reactive oxygen species and reactive nitrogen species. Hydrogen peroxide triggers cleavage of boronic ester and followed by intramolecular nucleophilic attack of the phenolic oxygen to the nitrile group resulting cyclized iminocoumarin-benzothiazoles and iminocoumarin, respectively. HP1 and HP2 are shown their ability to map intercellular accumulation of hydrogen peroxide in HeLa cells.
iii
Chapter 4 reports engineering boron-dipyrromethene (BODIPY) scaffold for chemosensing. A new boron–dipyrromethene (BODIPY) derivative (FS1) containing two triazole units exhibits an enhanced fluorescence in the presence of Hg2+ ions and a high selectivity for Hg2+ ions over competing metal ions in methanol: Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe2+, Fe3+, K+, Mg2+, Mn2+, Ni2+, Pb2+, and Zn2+ produced only minor changes in the fluorescence of FS1. The apparent dissociation constant (Kd) of FS1–Hg2+ was found to be 62 μM. Moreover, fluorescence microscopy experiments showed that FS1 can be used as a fluorescent probe for detecting Hg2+ ions in living cells.
Chapter 5 discusses a new monostyryl boron dipyrromethene derivative (MS1) which is appended with two triazole units and indicates the presence of Hg2+ among other metal ions with high selectivity by color change and red emission. Upon Hg2+ binding, the absorption band of MS1 is blue-shifted by 29 nm due to the inhibition of the intramolecular charge transfer from the nitrogen to the BODIPY, resulting in a color change from blue to purple. Significant fluorescence enhancement is observed with MS1 in the presence of Hg2+; the metal ions Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe2+, Fe3+, K+, Mg2+, Mn2+, Ni2+, Pb2+, and Zn2+ cause only minor changes in the fluorescence of the system. The apparent association constant (Ka) of Hg2+ binding in MS1 is found to be 1.864 × 105 M−1. In addition, fluorescence microscopy experiments show that MS1 can be used as a fluorescent probe for detecting Hg2+ in living cells.
Chapter 6 describes colorimetric detection of Hg2+ ion by an NBD dye. Upon Hg2+ recognition, the absorption band of CS1 is red-shifted by 39 nm and caused color change from orange to red. The absorption of CS1 is red sifted only in the presence of Hg2+; the metal ions Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe2+, V2+, Mg2+, Mn2+, Ni2+, and Zn2+ cause only minor changes in the absorbance spectra. The apparent association constant (Ka) of Hg2+-CS1 is found to be 1.71 × 104 M−1. In addition, NMR spectrometric titrations were also carried out to demonstrate Hg2+ binding event with CS1.

Abstract
Organic compounds have been used extensively to construct photo luminescent materials, solar cells and chemosensors. Its significance can be attributed to easy synthesis, inexpensive staring materials, easy to tune photo physical properties and easy to link with other supporting materials. Fluorescence sensing is a process in which interaction between species is detected by change in the fluorescence intensity of system. Organic dyes are ideally suited to be used as probes for fluorescence sensing. This work therefore is focused on synthesis of organic fluorophores and their applications in bioimaging.
Chapter 1 describes importance of chemosensors, mechanism of signal transduction, and parameters needed to optimize in every sensor. How organic dyes been used as fluorescent sensors is further explained in following chapters.
Chapter 2 describes the synthesis of BODIPY based fluorescent probes (HCS and HCS2) for hypochlorite sensing. Both probes exhibited highly sensitive to hypochlorite over other reactive oxygen species and reactive nitrogen species. HCS and HCS2 are virtually non-fluorescent as photo-induced electron transfer taking place from sulfur to BODIPY. Hypochlorite induced oxidation of sulfur to sulfoxide which inhibited the PET process and generates turn-on fluorescence in a molecule. This mechanism was further supported by DFT calculations (B3LYP/6-31G (d)). Both probes are shown their ability to map external addition and internal secretion of hypochlorite in RAW 264.7 cells.
Chapter 3 reports design, synthesis and characterization of hydrogen peroxide sensing probes HP1 and HP2. Both probes exhibited highly sensitive to hydrogen peroxide over other reactive oxygen species and reactive nitrogen species. Hydrogen peroxide triggers cleavage of boronic ester and followed by intramolecular nucleophilic attack of the phenolic oxygen to the nitrile group resulting cyclized iminocoumarin-benzothiazoles and iminocoumarin, respectively. HP1 and HP2 are shown their ability to map intercellular accumulation of hydrogen peroxide in HeLa cells.
iii
Chapter 4 reports engineering boron-dipyrromethene (BODIPY) scaffold for chemosensing. A new boron–dipyrromethene (BODIPY) derivative (FS1) containing two triazole units exhibits an enhanced fluorescence in the presence of Hg2+ ions and a high selectivity for Hg2+ ions over competing metal ions in methanol: Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe2+, Fe3+, K+, Mg2+, Mn2+, Ni2+, Pb2+, and Zn2+ produced only minor changes in the fluorescence of FS1. The apparent dissociation constant (Kd) of FS1–Hg2+ was found to be 62 μM. Moreover, fluorescence microscopy experiments showed that FS1 can be used as a fluorescent probe for detecting Hg2+ ions in living cells.
Chapter 5 discusses a new monostyryl boron dipyrromethene derivative (MS1) which is appended with two triazole units and indicates the presence of Hg2+ among other metal ions with high selectivity by color change and red emission. Upon Hg2+ binding, the absorption band of MS1 is blue-shifted by 29 nm due to the inhibition of the intramolecular charge transfer from the nitrogen to the BODIPY, resulting in a color change from blue to purple. Significant fluorescence enhancement is observed with MS1 in the presence of Hg2+; the metal ions Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe2+, Fe3+, K+, Mg2+, Mn2+, Ni2+, Pb2+, and Zn2+ cause only minor changes in the fluorescence of the system. The apparent association constant (Ka) of Hg2+ binding in MS1 is found to be 1.864 × 105 M−1. In addition, fluorescence microscopy experiments show that MS1 can be used as a fluorescent probe for detecting Hg2+ in living cells.
Chapter 6 describes colorimetric detection of Hg2+ ion by an NBD dye. Upon Hg2+ recognition, the absorption band of CS1 is red-shifted by 39 nm and caused color change from orange to red. The absorption of CS1 is red sifted only in the presence of Hg2+; the metal ions Ag+, Ca2+, Cd2+, Co2+, Cu2+, Fe2+, V2+, Mg2+, Mn2+, Ni2+, and Zn2+ cause only minor changes in the absorbance spectra. The apparent association constant (Ka) of Hg2+-CS1 is found to be 1.71 × 104 M−1. In addition, NMR spectrometric titrations were also carried out to demonstrate Hg2+ binding event with CS1.

Contents Page No
ABSTRACT i
DEDICATION iii
ACKNOWLEDGEMENT iv
DECLARATION v
ACRONYMS vi
CONTENTS viii
CONTENT OF FIGURES xiii
CONTENT OF TABLES xx
CONENT OF SCEMES xxi
Chapter 1 Theoretical Features of Fluorescence Sensing
1.1 Importance of Chemosensors 01
1.2 Classical design of Fluorescent sensors 01
1.3 Mechanism of Signal Transduction 01
1.3.1 Chemosensors 01
1.3.2 Chemodosimeter 02
1.4 Photo-induced Electron Transfer 03
1.5 Intra Molecular Charge Transfer 04
1.5.1 ICT mechanism 05
1.6 Detection Mechanism 05
1.6.1 Fluorophore having inert substituent 06
1.6.2 Fluorophore with electron donating and withdrawing
groups (OFF state) 06
1.6.3 Metal ion sensing (ON state) 07
1.7 References 07
Chapter 2
Development of BODIPY-Based Fluorescence Probes Selective for Hypochlorite and Their Applications for Biological Imaging
2.1 Introduction 08
2.2 Fluorogenic probes for ROS in bioimaging 09
2.2.1 Hydrogen peroxide sensing probes. 09
2.2.2 Hydroxyl radical detecting fluorescent and luminescent probes 10
2.2.3 Fluorescent probes for singlet oxygen 11
2.2.4 Probes for superoxide radical 12
2.2.5 Probes for hypochlorous acid/hypochlorite 12
2.2.6 Probes for ozone 13
2.3 Fluorescent probes to detect RNS 13
2.3.1 Probes for nitric oxide 13
2.3.2 Probes for peroxynitrite 14
2.4 A Highly Selective Green Light Emitting Probe for Hypochlorite..…16
2.4.1 Importance of Hypochlorite Sensors 16
2.4.2 Objectives 16
2.4.3 Synthesis 17
2.4.4 Photo physical properties 17
2.4.5 Selectivity 18
2.4.6 Reaction kinetics 19
2.4.7 Effect of pH 20
2.4.8 Electrochemical study 21
2.4.9 Crystal Structure 25
2.4.10 Detection of intracellular generation of HOCl in RAW 264.7 cells …27
2.4.11 Metal ion selectivity 28
2.4.12 Calculation of fluorescence quantum yield 29
2.5 Synthesis and characterization of hypochlorite sensing probe HCS2 …31
2.5.1 Introduction 31
2.5.2 Synthesis 31
2.5.3 Photo physical properties 32
2.5.4 Selectivity 32
2.5.5 Effect of pH 34
2.5.6 Electrochemical study 34
2.5.7 Crystal Structure 38
2.5.8 Bioimaging 40
2.6. Conclusion 41
2.7. Experimental Section 41
2.8 References 44
Chapter 3 Fluorogenic Probes for detection of Hydrogen peroxide in HeLa cells
3.1 Introduction 48
3.2 Synthesis 48
3.3 Photo Physical properties 49
3.4 Selectivity 51
3.5 Bioimaging 55
3.6 Conclusion 56
3.7 Experimental section 56
3.8 References 59
Chapter 4 Engineering Boron-dipyrromethene Scaffold (BODIPY) for Chemosensing
4.1 Introduction to BODIPY Fluorophores 60
4.2 Substituent effect on pyrrole units of BODIPY core 61
4.3 Electrophilic substitution 61
4.4 Substituent effect on 3, 5 position of BODIPY core 62
4.5 Substituent effect on Boron atom of BODIPY core 62
4.6 Chemosensors 63
4.6.1 Sensors for redox active molecules 64
4.6.2 pH probes 65
4.6.3 Metal-chelators 65
4.6.4 Logic gates 66
4.6.5 Labeling Biomolecule 67
4.7 Selective Detection of Neurofibrillary Tangles in the Brains of Alzheimer’s disease Patients 67
4.8 Bifunctional Reporter for Hybrid Optical/Positron Emission Tomography Imaging 68
4.9 A BODIPY based Highly Selective Turn-on Fluorescent Chemosensor
for Hg2+ Ions and Its Application to Live Cell Imaging 69
4.9.1 Synthesis of FS1 70
4.9.2 Cation sensing selectivity 71
4.9.3 Competitive test 73
4.9.4 Stoichiometry and Dissociation constant 74
4.9.5 Limit of Detection 75
4.9.6 NMR titration 76
4.9.7 Live Cell Imaging 76
4.9.8 Conclusion 78
4.9.9 Experimental section 78
4.9.10 Non-Linear Regression Analysis 80
4.9.11 Procedure for Fluorescence imaging 81
4.9.12 References 81
Chapter 5
Synthesis of Styryl group functionalized BODIPY Fluorophore and Its Applications
5.1 Introduction 84
5.2 Synthesis of near IR emitters by Knoevenagel condensation reactions 84
5.3 Metal ion sensors 85
5.4 Labeling of biological significant amines by BODIPY probes 86
5.5 Photodynamic therapy (PDT) sensitizers 86
5.6 BODIPY-Metal complex conjugates 87
5.7 pH Sensors 88
5.8 Metal Catalyzed Coupling Reactions at the 3- and 5-Positions 89
5.9 Design Strategies for Ratio metric Chemosensors 89
5.10 Molecular Probe for Imaging of Cerebral β-Amyloid Plaques 90
5.11 Glucagon imaging 91
5.12 A Colorimetric and Fluorometric detection of Hg2+ Ions by based BODIPY probe 92
5.12.1 Outline of Design 92
5.12.2 Synthesis of MS1 93
5.12.3 Photo physical properties 94
5.12.4 Cation sensing selectivity 95
5.12.5 Competitive test 98
5.12.6 Stoichiometry and Apparent association constant 98
5.12.7 Limit of Detection 100
5.12.8 Effect of pH 101
5.12.9 NMR Titration 102
5.12.10 Living cell imaging 104
5.12.11 Conclusion 104
5.12.12 Experimental procedures 105
5.12.13 Determination of the binding stoichiometry and the apparent dissociation constants for the binding of Hg(II) to MS1 107
5.12.14 Fluorescence imaging 108
5.13 References 108
Chapter 6
Fluorogenic and Chromogenic Chemosensors for Biomolecules Detection by a NBD Dye
6.1 Introduction 111
6.2 Salient features of NBD Fluorophore 111
6.3 Colorimetric sensor for Hg2+ based on NBD dye 111
6.3.1 Synthesis of CS1 112
6.3.2 Result and discussion 113
6.3.3 NMR Titration 117
6.3.4 Conclusion….. 118
6.3.5 Experimental procedure 118
6.3.6 Metal ion binding study by UV-vis spectroscopy 119
6.3.7 Determination of the binding stoichiometry and the association constant (KA) 119
6.4 References 119
Chapter 7 Supplementary Information 122

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