The syntheses of octasubstituted and unsusbstitituted Gallium(III) chloride and indium(III) chloride phthalocyanines (GaPc and InPc), their photophysical, photochemical and nonlinear optical parameters are hereby presented. The photocatalytic oxidation of 1-hexene using the synthesized GaPc and InPc complexes as well as electrochemical characterization is also presented in this thesis. Fluorescence quantum yields do not vary much among the four Ga complexes, except for complex 21c; therefore it was concluded that the effect of substituents is not significant among them. Solvents however, had an effect on the results. Lower Φ[subscript F] values were obtained in low viscosity solvents like toluene, relative to highly viscous solvents, such as DMSO. The triplet quantum yields were found to be lower in DMSO than in DMF and toluene. The rate constants for fluorescence, intersystem crossing and internal conversion as well as fluorescence and triplet lifetimes are reported. Photodegradation and singlet oxygen quantum yields have also been reported. There was no clear correlation between the latter parameters. It was however established that the four gallium MPcs were stable, within the allowed stability range for phthalocyanines. High quantum yields of triplet state (Φ[subscript T] ranging from 0.70 to 0.91 in dimethysulfoxide, DMSO) and singlet oxygen generation (Φ[subscript greek capital letter delta], ranging from 0.61 to 0.79 in DMSO) were obtained. Short triplet lifetimes 50 to 60 μs were obtained in DMSO). Calculated non-linear parameters of these complexes are compared with those of the corresponding GaPc derivatives and tetrasubstituted GaPc and InPc complexes. The optical limiting threshold intensity (I[subscript lim]) values for the InPc and GaPc derivatives were calculated and compared with those of corresponding tetrasubstituted InPc and GaPc complexes. The octasubstituted were found to be better optical limiters. Photocatalytic oxidation of 1-hexene by GaPc (21a-c) and InPc (22a-c) derivatives is also presented. The photocatalytic oxidation products for 1-hexene were 1,2- epoxyhexane and 1-hexen-3-ol. The % conversion values of 1-hexene and % selectivity of 1,2-epoxyhexane were generally higher for InPc derivatives. Even though InPc derivatives showed better photocatalytic results than GaPc derivatives, the former were less stable relative to the latter. Both type I and type II mechanism were implicated in the photocatalysis mechanism.

Four different trivalent and tetravalent metal phthalocyanine systems (chlorogallium, chloroindium, vanadyl, and titanyl phthalocyanines) were used singly to prepare thin films (0.05-2.0 micron thickness) on gold, optically transparent substrates. The photoelectronic properties of these electrodes could be modified either by altering the growth conditions (i.e. rate of sublimation, cleanliness of substrate) or by dosing the thin films with either hydrogen or oxygen at elevated temperatures (150°C). The properties of these thin films were monitored by electron microscopy, UV-visible spectrophotometry, X-ray and Ultra-violet surface spectroscopies, and a variety of electrochemical and photoelectrochemical techniques. All four systems behaved in a manner similar to a p-type semiconductor when prepared at rapid rates (10-20 A/min) on gold substrates. In the dark, for contacting redox couples with Eᵒ’ values negative of +0.6V, the phthalocyanine electrodes showed negligible dark currents. Upon illumination, the photoelectrodes only produced positive photopotentials. Chlorogallium phthalocyanine thin films could be made to produce both positive and negative photopotentials when grown at slow rates (1-5 A/min) on clean, gold substrates. These chlorogallium phthalocyanine electrodes regained the properties of a p-type semiconductor after being dosed with oxygen for 48 hours at 150°C. X-ray Photoelectron Spectroscopy confirmed the presence of a high concentration of oxygen at the surface of all of the p-type phthalocyanine electrodes. The oxygen may accept electron density from the phthalocyanine macrocycle to cause the Fermi level to move down in energy toward its valence band edge. Dosing the film with hydrogen caused the electrode to exhibit its original intrinsic characteristics. This variability in electrical properties as a function of gas dopant may lead to the development of a sensitive gas sensing device. Ultra-violet Photoelectron Spectroscopy, as well as molecular orbital calculations, were applied to the chlorogallium phthalocyanine system to determine the molecular orbital contributions to its valence and conduction bands. Photoelectrochemical cells made from electrodes of chlorogallium and vanadyl phthalocyanines exhibited power conversion efficiencies in excess of 0.1%. The vanadyl and titanyl phthalocyanine electrodes were also effective catalysts for the photoreduction of H⁺ to H₂.

by Michael Tsang Ming Choi. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1999. / Includes bibliographical references (leaves 85-90). / Abstracts in English and Chinese. / ACKNOWLEDGMENT --- p.i / TABLE OF CONTENTS --- p.ii / LIST OF FIGURES --- p.iv / LIST OF TABLES --- p.vi / ABBREVIATIONS --- p.vii / ABSTRACT --- p.viii / 摘要 --- p.ix / Chapter PART I. --- "SYNTHESIS, SPECTROSCOPIC PROPERTIES AND AGGREGATION BEHAVIOR OF SUBSTITUTED 2,3- NAPHTHALOCYANINES" / Chapter 1 --- INTRODUCTION --- p.2 / Chapter 1.1 --- "Synthesis of 2,3 -Naphthalocyanines" --- p.6 / Chapter 1.2 --- Aggregation Phenomena of Phthalocyanines --- p.14 / Chapter 1.3 --- Phthalocyanines with Crown Ether Voids --- p.20 / Chapter 2 --- RESULTS AND DISCUSSION --- p.26 / Chapter 2.1 --- "Synthesis of Substituted 2,3-Naphthalocyanines" --- p.26 / Chapter 2.2 --- Synthesis of Substituted Phthalocyanines --- p.29 / Chapter 2.3 --- "Characterization of 2,3-Naphthalocyanines and Phthalocyanines" --- p.31 / Chapter 2.4 --- "Aggregation Behavior of Octasubstituted 2,3-Naphthalocyanines and Phthalocyanines" --- p.34 / Chapter 2.5 --- Liquid Crystalline Properties of64 --- p.43 / Chapter 2.6 --- "Synthesis of a Crown Ether-Substituted 2,3-Naphthalocyanine" --- p.45 / Chapter 2.7 --- Conclusion --- p.48 / Chapter 3 --- EXPERIMENTAL SECTION --- p.49 / Chapter 3.1 --- Materials --- p.49 / Chapter 3.2 --- Physical Measurements --- p.49 / Chapter 3.3 --- General Procedure for the Preparation of Dinitriles --- p.50 / Chapter 3.4 --- General Procedure for the Cyclization of Dinitriles --- p.53 / Chapter PART II. --- SYNTHETIC STUDIES OF SUBSTITUTED DICYANO-ANTHRACENES AND TETRACENES / Chapter 1 --- INTRODUCTION --- p.57 / Chapter 2 --- RESULTS AND DISCUSSION --- p.63 / Chapter 2.1 --- Synthesis of Substituted Anthracenes --- p.63 / Chapter 2.2 --- Synthesis of Substituted Tetracenes --- p.72 / Chapter 2.3 --- Conclusion --- p.77 / Chapter 3 --- EXPERIMENTAL SECTION --- p.78 / REFERENCES --- p.85 / Chapter APPENDIX --- Crystallographic data of dimer of anthracene118 --- p.91

by Chi-Hang Lee. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2002. / Includes bibliographical references (leaves 71-80). / Abstracts in English and Chinese. / ABSTRACT --- p.i / ACKNOWLEDGMENT --- p.iv / TABLE OF CONTENTS --- p.v / LIST OF SCHEMES --- p.vii / LIST OF FIGURES --- p.viii / LIST OF TABLES --- p.x / ABBREVIATIONS --- p.xi / Chapter 1 --- Introduction --- p.1 / Chapter 1.1 --- Discovery of Phthalocyanines --- p.1 / Chapter 1.2 --- Synthesis of Phthalocyanines --- p.4 / Chapter 1.2.1 --- Metal-Free Phthalocyanines --- p.4 / Chapter 1.2.2 --- Metallophthalocyanines (MPcs) --- p.5 / Chapter 1.2.3 --- Sandwich Complexes (MPc2) --- p.7 / Chapter 1.2.4 --- Tetra-Substituted Phthalocyanines --- p.8 / Chapter 1.2.5 --- "2,3,9,10,16,17,23,24-Octa-substituted Phthalocyanines" --- p.11 / Chapter 1.2.6 --- "1,4,8,11,15,18,22,25-Octa-substituted Phthalocyanines" --- p.12 / Chapter 1.3 --- Mechanism for Phthalocyanine Formation --- p.14 / Chapter 1.4 --- Purification of Phthalocyanines --- p.16 / Chapter 1.5 --- Characteristics of Phthalocyanines --- p.17 / Chapter 1.5.1 --- Electronic Structure --- p.17 / Chapter 1.5.2 --- Absorption Spectra --- p.17 / Chapter 1.5.3 --- X-Ray Diffraction Studies --- p.19 / Chapter 1.6 --- Applications of Phthalocyanines --- p.20 / Chapter 1.6.1 --- Colorants --- p.20 / Chapter 1.6.2 --- Photodynamic Therapy --- p.21 / Chapter 1.6.3 --- Catalysis --- p.22 / Chapter 2 --- Results and Discussion --- p.23 / Chapter 2.1 --- "Preparation, Spectroscopic Properties, and Structure of Phthalocyanines Substituted with Four 2,4-Dimethyl-3- pentyloxy Moieties" --- p.23 / Chapter 2.1.1 --- Synthetic Studies --- p.24 / Chapter 2.1.2 --- UV-Vis Spectra --- p.28 / Chapter 2.1.2.1 --- Effects of Metal Center --- p.28 / Chapter 2.1.2.2 --- Effects of Substituents --- p.30 / Chapter 2.1.2.3 --- Effects of Concentration --- p.30 / Chapter 2.1.2.4 --- Absorption Spectra of MnClPc(OC7H15)4 (10) --- p.34 / Chapter 2.1.3 --- 1H NMR Spectra --- p.35 / Chapter 2.1.4 --- Structural Studies --- p.38 / Chapter 2.1.4.1 --- Molecular Structures of ZnPc(OC7H15)4 (3) and CoPC(OC7H15)4 (5) --- p.39 / Chapter 2.1.4.2 --- Molecular Structure of MnClPc(OC7H15)4 (10) --- p.41 / Chapter 2.2 --- Formation and Crystal Structures of Novel Inclusion Complexes of Phthalocyanines and Oxalic Acid --- p.43 / Chapter 2.2.1 --- 1:1Complex with Metal-free Phthalocyanine (8) --- p.43 / Chapter 2.2.2 --- 1:1Complexes with Palladium Phthalocyanine (4) --- p.49 / Chapter 2.2.3 --- Conclusion --- p.51 / Chapter 2.3 --- Cerium Promoted Formation of Metal-Free Phthalocyanines --- p.52 / Chapter 2.3.1 --- Introduction --- p.52 / Chapter 2.3.2 --- Preparation of Metal-free Phthalocyanines --- p.52 / Chapter 2.3.3 --- Conclusion --- p.58 / Chapter 3 --- Experimental --- p.59 / Chapter 3.1 --- General --- p.59 / Chapter 3.2 --- "Synthesis of 3-(2,4-dimethyl-3-pentyloxy)phthalonitrile (2)" --- p.60 / Chapter 3.3 --- "Synthesis of ZnPc(OC7H,5)4 (3 and 6)" --- p.61 / Chapter 3.4 --- Synthesis of PdPc(OC7H15)4 (4 and 7) --- p.62 / Chapter 3.5 --- Synthesis of CoPc(OC7H15)4 (5) --- p.64 / Chapter 3.6 --- Synthesis of H2Pc(OC7H15)4 (8) --- p.64 / Chapter 3.7 --- Synthesis of MnClPc(OC7H15)4 (10) --- p.66 / Chapter 3.8 --- General Procedure for the Cerium-Promoted Cyclization of Phthalonitriles --- p.67 / Chapter 3.9 --- X-ray Crystallographic Analyses --- p.69 / Chapter 4 --- REFERENCES --- p.71 / APPENDIX A lH and13 C̐ưث1H} NMR spectra / APPENDIX B X-ray Crystallographic Data

by Man-Wai Woo. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2002. / Includes bibliographical references (leaves 77-81). / Abstracts in English and Chinese. / ABSTRACT --- p.i / ACKNOWLEDGMENT --- p.iii / CONTENTS --- p.iv / LIST OF FIGURES --- p.vi / LIST OF TABLES --- p.ix / ABBREVIATIONS --- p.x / Chapter 1. --- INTRODUCTION / Chapter 1.1 --- General Background of Phthalocyanines --- p.1 / Chapter 1.2 --- Previous Examples of Phthalocyanine-containing Polymers --- p.5 / Chapter 1.2.1 --- Poly(phthalocyanines) Linked Via Peripheral Substituents --- p.5 / Chapter 1.2.2 --- Poly(phthalocyanines) Linked Via Axial Ligation --- p.7 / Chapter 1.2.3 --- Poly(phthalocyanines) Attached Laterally to a Polymer Backbone --- p.11 / Chapter 1.3 --- Ring Opening Metathesis Polymerization (ROMP) --- p.15 / Chapter 1.4 --- ROMP of Norbornene Substituted Porphyrazine --- p.18 / Chapter 2. --- RESULTS AND DISCUSSION / Chapter 2.1 --- Phthalocyanines Substituted with Four Poly(norbornene)s --- p.20 / Chapter 2.1.1 --- Preparation of Tetra(norbornene) Phthalocyanines --- p.20 / Chapter 2.1.2 --- Polymerization of Tetra(norbornene) Phthalocyanines --- p.30 / Chapter 2.1.3 --- Characterization of Polymers --- p.39 / Chapter 2.1.4 --- Photophysical Properties of the Polymers --- p.43 / Chapter 2.2 --- Phthalocyanines Substituted with One Poly(norbornene) --- p.49 / Chapter 2.2.1 --- Preparation and Polymerization of Mono(norbornene) Phthalocyanines --- p.49 / Chapter 2.2.2 --- Characterization of the Polymers 41 - 44 --- p.56 / Chapter 2.2.3 --- Fluorescence Quenching of 40 Polymers 41 -44 --- p.61 / Chapter 2.2.4 --- Preparation of Water-soluble Poly(7-oxanorbornene) --- p.63 / Chapter 2.3 --- Conclusion --- p.65 / Chapter 3 --- EXPERIMENTAL SECTION --- p.66 / Chapter 3.1 --- General Methods --- p.66 / Chapter 3.2 --- Photophysical Measurements --- p.67 / Chapter 3.3 --- Synthesis of Phthalocyanines with Four Poly(norbornene) Substituents --- p.68 / Chapter 3.4 --- Synthesis of Phthalocyanines with One Poly(norbornene) Substituent --- p.74 / Chapter 4. --- REFERENCES --- p.77

by Roger Chun Wang Liu. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1996. / Includes bibliographical references (leaves 98-108). / ACKNOWLEDGEMENTS --- p.i / CONTENTS --- p.ii / ABBREVIATIONS --- p.v / LIST OF FIGURES --- p.vi / LIST OF TABLES --- p.vii / Chapter I. --- THE CHEMISTRY OF METALLO-PHTHALOCYANINES AND -NAPHTHALOCYANINES --- p.1 / ABSTRACT --- p.2 / Chapter 1. --- SANDWICH-LIKE BIS(PHTHALOCYANINATO)LANTHANIDE COMPLEXES / Chapter 1.1. --- Introduction --- p.3 / Chapter 1.2. --- Preparation of Substituted Phthalonitriles --- p.8 / Chapter 1.3. --- Condensation of Phthalonitrile --- p.9 / Chapter 1.4. --- Condensation of Substituted Phthalonitriles --- p.10 / Chapter 1.5. --- Spectroscopic and Electrochemical Properties --- p.12 / Chapter 1.6. --- Conclusion --- p.21 / Chapter 2. --- "SUBSTITUTED 2,3-NAPHTHALOCYANINES" / Chapter 2.1. --- Introduction --- p.22 / Chapter 2.2. --- Preparation of Alkyl-Substituted Dicyanonaphthalenes --- p.26 / Chapter 2.3. --- Preparation of Halo-Substituted Dicyanonaphthalenes --- p.30 / Chapter 2.4. --- Condensation of Alkyl-Substituted Dicyanonaphthalenes --- p.30 / Chapter 2.5. --- Condensation of Halo-Substituted Dicyanonaphthalenes --- p.35 / Chapter 2.6. --- Conclusion --- p.38 / Chapter 3. --- EXPERIMENTAL SECTION / Chapter 3.1. --- General Directions --- p.39 / Chapter 3.2. --- Preparation of Substituted Phthalonitriles --- p.40 / Chapter 3.3. --- Condensation of Phthalonitrile --- p.43 / Chapter 3.4. --- Condensation of Substituted Phthalonitriles --- p.44 / Chapter 3.5. --- Preparation of Alkyl-Substituted Dicyanonaphthalenes --- p.46 / Chapter 3.6. --- Preparation of Halo-Substituted Dicyanonaphthalenes --- p.49 / Chapter 3.7. --- Condensation of Alkyl-Substituted Dicyanonaphthalenes --- p.51 / Chapter 3.8. --- Condensation of Halo-Substituted Dicyanonaphthalenes --- p.52 / Chapter II. --- "SYNTHETIC STUDIES OF MIXED AZA-, OXA-, AND THIA-CROWN ETHERS" --- p.55 / ABSTRACT --- p.56 / Chapter 1. --- INTRODUCTION --- p.57 / Chapter 2. --- RESULTS AND DISCUSSION --- p.64 / Chapter 2.1. --- Preparation of Diols and Dithiols --- p.64 / Chapter 2.2. --- Preparation of Ditosylates --- p.66 / Chapter 2.3. --- 1:1 Cyclization -- Preparation of Monoaza- 15-crown-5 --- p.68 / Chapter 2.4. --- Crystal Structure of N-(4-methoxyphenyl) benzomonoaza-15- crown-5 (112) --- p.76 / Chapter 2.5. --- Complexation of Monoaza-15-crown-5 --- p.79 / Chapter 2.6. --- Conclusion --- p.80 / Chapter 3. --- MISCELLANEOUS SYNTHESES --- p.81 / Chapter 3.1. --- Preparation of Tetrabromodibenzo-24-crown-8 --- p.81 / Chapter 3.2. --- Complexation of Tetrabromodibenzo-24-crown-8 --- p.82 / Chapter 4. --- EXPERIMENTAL SECTION --- p.84 / Chapter 4.1. --- General Directions --- p.84 / Chapter 4.2. --- Preparation of Diols and Dithiols --- p.84 / Chapter 4.3. --- Preparation of Ditosylates --- p.88 / Chapter 4.4. --- 1:1 Cyclization -- Preparation of Monoaza- 15-crown-5 --- p.89 / Chapter 4.5. --- Complexation of Monoaza-15-crown-5 --- p.94 / Chapter 4.6. --- Preparation of Tetrabromodibenzo-24-crown-8 --- p.95 / Chapter 4.7. --- Complexation of Tetrabromodibenzo-24-crown-8 --- p.97 / REFERENCES AND NOTES --- p.98 / APPENDIX --- p.109

At the end of this thesis, 1H and 13C{ 1H} NMR spectra for all the new compounds and the crystallographic details for the X-ray structure are given as Appendices. / Chapter 1 presents an overview of photodynamic therapy, including its historical development, photophysial and biological mechanisms, and current clinical situation. A brief review of second-generation photosensitizers and the different approaches for targeted photodynamic therapy are also given. / Chapter 2 reports the synthesis and characterization of a silicon(IV) phthalocyanine which is substituted axially with two diamino moieties, together with its di- and tetramethylated derivatives. The non-methylated analogue shows a high photocytotoxicity toward HT29 human colorectal adenocarcinoma and HepG2 human hepatocarcinoma cells with IC50 values down to 0.01 muM. Interestingly, this compound also exhibits a pH-dependent behavior. The fluorescence quantum yield increases by four folds and the singlet oxygen quantum yield increases by three folds in water when the pH decreases from 7.0 to 5.0. The preliminary results suggest that this compound is a promising photosensitizer of which the photodynamic activity can be modulated by changing the pH of the environment. Furthermore, this compound can be used as a near-infrared fluorescence probe for optical imaging of intracellular acidic level. / Chapter 3 reports a novel series of aminophenyl-substituted silicon(IV) phthalocyanines. The aminophenyl moieties in these conjugates can also modulate the photophysical and photosensitizing properties of the phthalocyanine core through changing the pH of the environment. These phthalocyanines exhibit a low photocytotoxicity under physiological conditions (pH 7.4). It is likely that the amino groups, in the free amine form, can quench the singlet excited state of phthalocyanine by a photoinduced electron transfer (PET) mechanism, and reduce the chance of intersystem crossing and the efficiency in generating singlet oxygen. The strong aggregation tendency of these compounds in this pH environment is another major reason for the low photocytotoxicity. When the pH is lower to 6.4-6.9, the amino groups are protonated so that they are no longer electron donors, and the compounds become less aggregated. These changes lead to an increase in photocytotoxicity. The results of this study are reported in this Chapter. / Chapter 4 describes a new series of silicon(IV) phthalocyanines conjugated axially with various polyamine derivatives. Polyamines are naturally occurring compounds which are involved in a number of cell processes including cell proliferation and differentiation. Their biosynthetic activity and polyamine levels in some tumor cells are significantly higher than those in normal cells. Conjugation of polyamine analogues is therefore one of the promising approaches to improve the tumor-targeting property of photosensitizers. This Chapter describes the synthesis, spectroscopic characterization, and photophysical properties of these compounds. Their photodynamic activities toward HT29 and Chinese hamster ovary (CHO) cells have also been studied in detail. Their cellular uptake, subcellular localization, cell death mechanism, and in vivo photocytotoxicity have also been studied. / In Chapter 5, we report a series of silicon(IV) phthalocyanines containing one or two cholesterol unit(s) at the axial position(s), including their synthesis, spectroscopic characterization, photophysical properties, and in vitro photodynamic activities. These cholesterol-containing photosensitizers can form stable conjugates with low-density lipoprotein (LDL), which is the major lipoprotein carrier for cholesterol in human plasma. On the basis that cancer cells generally express significantly more LDL receptors than normal cells, these cholesterol-conjugated phthalocyanines are designed with a view to enhancing their selectivity toward tumor. Unfortunately, conjugation of cholesterol reduces the photodynamic activity of the silicon(IV) phthalocyanines as a result of their higher aggregation tendency. / This thesis reports the synthesis, spectroscopic characterization, and photophysical and biological properties of several series of novel silicon(IV) phthalocyanines which are specially designed as efficient and selective photosensitizers for photodynamic therapy. / Jiang, Xiongjie. / Source: Dissertation Abstracts International, Volume: 72-01, Section: B, page: . / Thesis (Ph.D.)--Chinese University of Hong Kong, 2010. / Includes bibliographical references and index. / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Electronic reproduction. Ann Arbor, MI : ProQuest Information and Learning Company, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstract also in Chinese.

Lau, Ting Fong Janet. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2008. / Includes bibliographical references. / Abstracts in English and Chinese. / Abstract --- p.iii / Abstract (in Chinese) --- p.v / Acknowledgment --- p.vii / Table of Contents --- p.ix / List of Figures --- p.xiii / List of Tables --- p.xix / List of Schemes --- p.xxi / Abbreviations --- p.xxiii / Chapter Chapter 1 --- Introduction / Chapter 1.1 --- General --- p.1 / Chapter 1.1.1 --- History of Phthalocyanines --- p.1 / Chapter 1.1.2 --- General Synthesis --- p.2 / Chapter 1.1.3 --- Properties and Usage of Phthalocyanines --- p.8 / Chapter 1.2 --- Phthalocyanines as Efficient Photosensitizers for Photodynamic Therapy --- p.9 / Chapter 1.2.1 --- Photophysical and Biological Mechanisms of Photodynamic Therapy --- p.10 / Chapter 1.2.2 --- Photosensitizers in Photodynamic Therapy --- p.13 / Chapter 1.2.2.1 --- First-Generation Photosensitizers --- p.13 / Chapter 1.2.2.2 --- Second-Generation Photosensitizers --- p.16 / Chapter 1.2.2.3 --- Phthalocyanine-Based Photosensitizers --- p.20 / Chapter 1.3 --- An Introduction on Supramolecular Chemistry --- p.27 / Chapter 1.3.1 --- Phthalocyanine-Based Supramolecular Systems --- p.28 / Chapter 1.3.2 --- Mixed Porphyrin-Phthalocyanine Supramolecular Assemblies --- p.31 / Chapter 1.4 --- Cyclodextrins as Building Blocks for Supramolecular Structures --- p.38 / Chapter 1.4.1 --- Background of Cyclodextrins --- p.38 / Chapter 1.4.2 --- Phthalocyanine-Cyclodextrin Supramolecular Systems --- p.41 / Chapter 1.5 --- Objectives of This Study --- p.47 / Chapter 1.6 --- References --- p.47 / Chapter Chapter 2 --- Permethylated β-Cyclodextrin Disubstituted Silicon(IV) Phthalocyanines / Chapter 2.1 --- Introduction --- p.55 / Chapter 2.2 --- Results and Discussion --- p.57 / Chapter 2.2.1 --- Preparation and Characterization --- p.57 / Chapter 2.2.2 --- Electronic Absorption and Photophysical Properties --- p.62 / Chapter 2.2.3 --- In vitro Photodynamic Activities --- p.66 / Chapter 2.3 --- Conclusion --- p.73 / Chapter 2.4 --- Experimental Section --- p.73 / Chapter 2.4.1 --- General --- p.73 / Chapter 2.4.2 --- Photophysical Measurements --- p.74 / Chapter 2.4.3 --- Synthesis --- p.75 / Chapter 2.4.4 --- Cell Lines and Culture Conditions --- p.83 / Chapter 2.4.5 --- Photocytotoxicity Assay --- p.83 / Chapter 2.4.6 --- ROS Measurements --- p.84 / Chapter 2.4.7 --- Microscopic Studies --- p.85 / Chapter 2.4.8 --- Subcellular Localization Studies --- p.85 / Chapter 2.5 --- References --- p.86 / Chapter Chapter 3 --- Unsymmetrically Substituted β-Cyclodextrin-Appended Silicon(IV) Phthalocyanines / Chapter 3.1 --- Introduction --- p.89 / Chapter 3.2 --- Results and Discussion --- p.90 / Chapter 3.2.1 --- Preparation and Characterization --- p.90 / Chapter 3.2.2 --- Electronic Absorption and Photophysical Properties --- p.94 / Chapter 3.2.3 --- In vitro Photodynamic Activities --- p.98 / Chapter 3.3 --- Conclusion --- p.107 / Chapter 3.4 --- Future Work --- p.108 / Chapter 3.5 --- Experimental Section --- p.108 / Chapter 3.5.1 --- General --- p.108 / Chapter 3.5.2 --- Synthesis --- p.109 / Chapter 3.6 --- References --- p.114 / Chapter Chapter 4 --- Construction of Mixed Phthalocyanine-Porphyrin Systems through Host-Guest Interactions in Aqueous Media / Chapter 4.1 --- Introduction --- p.117 / Chapter 4.2 --- Results and Discussion --- p.119 / Chapter 4.3 --- Conclusion --- p.132 / Chapter 4.4 --- Experimental Section --- p.132 / Chapter 4.5 --- References --- p.133 / Appendix A Determination of Binding Constants --- p.135 / Appendix B 1H and 13C{1H} NMR Spectra --- p.137 / Appendix C Mass Spectra --- p.151

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