by Yee-On Yeung. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1997. / Includes bibliographical references (leaves 76-80). / Acknowledgment --- p.i / Contents --- p.ii / List of Figures --- p.v / List of Tables --- p.vi / Abbreviations --- p.vii / Abstract --- p.viii / Chapter 1. --- Introduction --- p.1 / Chapter 2. --- Results and Discussion / Chapter 2.1 --- "Synthesis of Differently Substituted 2,3-Naphthalocyaninatozinc(II) Complexes" / Chapter 2.1.1 --- Preparation of substituted dicyanonaphthalenes --- p.13 / Chapter 2.1.2 --- "Preparation of octasubstituted 2,3-naphthalocyaninatozinc(II) complexes" --- p.16 / Chapter 2.1.3 --- "Aggregation of octasubstituted 2,3-naphthalocyaninatozinc(II) complexes" --- p.27 / Chapter 2.1.4 --- "Effects of substituents on the electronic spectra of 2,3- naphthalocyaninatozinc(II) complexes" --- p.31 / Chapter 2.2 --- "Synthetic Studies of Liquid Crystals Based on a 2,3-Naphthalocyanine Core" / Chapter 2.2.1 --- Preparation of dicyanonaphthalenes substituted with long side chains --- p.34 / Chapter 2.2.2 --- "Preparation of liquid crystals based on 2,3-naphthalocyanine cores" --- p.36 / Chapter 2.2.3 --- Characterization of the liquid crystals --- p.42 / Chapter 2.3 --- Conclusions --- p.46 / Chapter 3. --- Experimental Section / Chapter 3.1 --- Materials --- p.47 / Chapter 3.2 --- Physical Measurements --- p.47 / Chapter 3.3 --- "Preparation of (1,6,10,15,19,24,28,33-octamethyl-2,3-naphthalocyaninato)- zinc(II) (62)" --- p.48 / Chapter 3.4 --- "Preparation of (1，6,10，15，19，24，28，33-octahexyl-2，3-naphthalocyaninato)- zinc(II) (63)" --- p.51 / Chapter 3.5 --- "Preparation of (2,5,11,14,20,23,29,32-octahexyl-1,6,10,15,19,24,28,33- octamethyl-2,3-naphthalocyaninato)zinc(II) (67)" --- p.54 / Chapter 3.6 --- "Preparation of (2,5,11,14,20,23,29,32-octahexy1-2,3-naphthalocyaninato- zinc(II)complex (64)" --- p.58 / Chapter 3.7 --- "Preparation of (3,4,12,13,21,22,30,31-octapropylthio-2,3- naphthalocyaninato)zinc(II) (65)" --- p.60 / Chapter 3.8 --- "Preparation of (3,4,12,13,21,22,30,31 -octaphenylthio-2,3- naphthalocyaninato)zinc(II) (66)" --- p.63 / Chapter 3.9 --- "Preparation of [2,5,11,14,20,23,29,32-octa(hexyloxymethyl)-2,3- naphthalocyaninato]zinc(II) (79)" --- p.64 / Chapter 3.10 --- "Preparation of [2,5,11,14,20,23,29,32-octa(methoxybutyl-digol)-2,3- naphthalocyaninato]zinc(II) (80)" --- p.68 / Chapter 3.11 --- "Preparation of [2,5,11,14,20,23,29,32-octa(dodecylthiomethyl)-2,3- naphthalocyaninato]zinc(II) (81)" --- p.70 / Chapter 3.12 --- "Preparation of [3,4,12,13,21,22,30,31 -octa(octylthio)-2,3- naphthalocyaninato]zinc(II) (82)" --- p.72 / Chapter 3.13 --- "Preparation of [3,4,12,13,21,22,30,31-octa(dodecylthio)-2,3- naphthalocyaninato]zinc(II) (83)" --- p.74 / References --- p.76 / "Appendix A IR spectra of octasubstituted ZnNc complexes (62, 63, 64，66)." --- p.81 / Appendix B Mass spectra of octasubstituted ZnNc complexes (63-66). --- p.85 / Appendix C Determination of aggregation number (n) and aggregation constant (K). --- p.89 / Appendix D 1H NMR spectra of octasubstituted ZnNc complexes (80，81，83). --- p.90 / "Appendix E 13C NMR spectra of octasubstituted ZnNc complexes (80，82, 83)." --- p.93

Lee Pui Sze Priscilla. / "October 2003." / Thesis (Ph.D.)--Chinese University of Hong Kong, 2003. / Includes bibliographical references. / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Mode of access: World Wide Web. / Abstracts in English and Chinese.

Anthony Chi Heng Ng. / "January 2002." / Thesis (Ph.D.)--Chinese University of Hong Kong, 2002. / Includes bibliographical references. / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Mode of access: World Wide Web. / Abstracts in English and Chinese.

Chan Wing Kin. / Thesis submitted in: Oct 2004. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2005. / Includes bibliographical references. / Abstracts in English and Chinese. / Abstract --- p.i / Abstract (in Chinese) --- p.iii / Acknowledgement --- p.iv / Table of Contents --- p.vi / List of Figures --- p.xi / List of Tables --- p.xv / List of Schemes --- p.xvi / Abbreviations --- p.xviii / Chapter Chapter 1 --- Introduction --- p.1 / Chapter 1.1 --- General Background of Phthalocyanines --- p.1 / Chapter 1.2 --- General Background of Liquid Crystals --- p.3 / Chapter 1.3 --- Structural Classification of the Mesophases --- p.6 / Chapter 1.3.1 --- The Columnar Liquid Crystals --- p.6 / Chapter 1.3.2 --- The Nematic Phase --- p.10 / Chapter 1.3.3 --- The Lamellar Phase --- p.11 / Chapter 1.4 --- Applications of Columnar Discotic Liquid Crystals --- p.13 / Chapter 1.4.1 --- General Properties of HATn Materials and Phthalocyanines --- p.13 / Chapter 1.4.2 --- Supramolecular Channels and Wires --- p.16 / Chapter 1.4.3 --- Phthalocyanine Based Gas Sensors --- p.21 / Chapter 1.5 --- General Synthesis of Liquid Crystalline Phthalocyanines --- p.23 / Chapter 1.5.1 --- Peripherally Substituted Phthalocyanines --- p.23 / Chapter 1.5.1.1 --- Octakis(alkoxymethy l)phthalocy anines --- p.23 / Chapter 1.5.1.2 --- Octa-alkoxyphthalocyanines --- p.26 / Chapter 1.5.1.3 --- Octa-alkylphthalocyanines --- p.29 / Chapter 1.5.1.4 --- Octakis-(alkoxycarbonyl)phthalocyanines --- p.30 / Chapter 1.5.1.5 --- Octa-(p-alkoxylphenyl)phthalocyanines --- p.32 / Chapter 1.5.1.6 --- Tetrakis[oligo(ethyleneoxy)] phthalocyanines --- p.34 / Chapter 1.5.2 --- Non-Peripherally Substituted Phthalocyanines --- p.35 / Chapter 1.5.2.1 --- Octa(alkoxymethyl)phthalocyanines --- p.35 / Chapter 1.5.2.2 --- Octa-alkylphthalocyanines --- p.37 / Chapter 1.5.3 --- Unsymmetrically Substituted Phthalocyanines --- p.40 / Chapter 1.5.4 --- Liquid Crystalline Metallophthalocyanines --- p.42 / Chapter 1.5.4.1 --- Copper Phthalocyanines --- p.42 / Chapter 1.5.4.2 --- "Manganese, Cobalt, Nickel, and Zinc Phthalocyanines" --- p.43 / Chapter 1.5.4.3 --- Lutetium Phthalocyanines --- p.43 / Chapter 1.5.4.4 --- "Silicon, Tin, and Lead Phthalocyanines" --- p.44 / Chapter 1.6 --- Summary --- p.45 / Chapter 1.7 --- References --- p.47 / Chapter Chapter 2 --- "Syntheses, Aggregation Behavior and Liquid Crystalline Properties of Peripherially Octaalkynyl Phthalocyanines" --- p.57 / Chapter 2.1 --- Synthesis and Characterization of Octaalkynyl Phthalocyanines --- p.57 / Chapter 2.1.1 --- Preparation of Alkynyl Fragment 22 --- p.57 / Chapter 2.1.2 --- Preparation of Alkynyl Phthalonitrile 23 --- p.58 / Chapter 2.1.3 --- "Synthesis and Characterization of [2,3,9,10,16,17,23,24-Octakis(3,4,5-tris (dodecyloxy)phenylethynyl)phthalocyaninato]magnesium(II) (29)" --- p.62 / Chapter 2.2 --- Electronic Absorption of Alkynylated Phthalocyanine 29 --- p.65 / Chapter 2.3 --- Liquid Crystalline Properties of Alkynyl Phthalocyanine 29 --- p.71 / Chapter 2.4 --- Summary --- p.73 / Chapter 2.5 --- Experimental Section --- p.74 / Chapter 2.5.1 --- General Information --- p.74 / Chapter 2.5.2 --- Physical Measurements --- p.74 / Chapter 2.5.3 --- Photophysical Measurements --- p.75 / Chapter 2.5.4 --- Experimental Procedure --- p.76 / Chapter 2.6 --- References --- p.83 / Chapter Chapter 3 --- Facile Synthesis of Liquid Crystalline Phthalocyanines Through Transesterification Reactions --- p.86 / Chapter 3.1 --- Synthesis and Characterization --- p.86 / Chapter 3.1.1 --- "Preparation of 4,5-bis(4-methoxycarbonylphenoxy)phthalonitrile (30)" --- p.86 / Chapter 3.1.2 --- Preparation of Phthalocyanines --- p.87 / Chapter 3.2 --- Electronic Absorption Properties and Aggregation Behavior --- p.91 / Chapter 3.3 --- Liquid Crystalline Properties of Phthalocyanines 31 -37 --- p.101 / Chapter 3.4 --- Summary --- p.104 / Chapter 3.5 --- Experimental Section --- p.105 / Chapter 3.5.1 --- Experimental Procedure --- p.105 / Chapter 3.6 --- References --- p.114 / Chapter Chapter 4 --- "In vitro Photodynamic Activities of Peripherially Octa-substituted Zinc Phthalocyanines with Terminal Mono-, Di- and Triethylene Glycol Chains" --- p.115 / Chapter 4.1 --- Photodynamic Therapy (PDT) --- p.115 / Chapter 4.1.1 --- Brief Introduction of Photodynamic Therapy --- p.115 / Chapter 4.1.2 --- Photophysical Mechanism Involved in PDT --- p.117 / Chapter 4.2 --- Photophysical Properties of Phthalocyanines 34-36 --- p.119 / Chapter 4.2.1 --- An overview of photochemical and photophysical processes --- p.119 / Chapter 4.2.2 --- Spectroscopic and Photophysical Properties of Phthalocyanines 34-36 --- p.122 / Chapter 4.3 --- In vitro Photodynamic Activities --- p.128 / Chapter 4.4 --- Summary --- p.128 / Chapter 4.5 --- Experimental Section --- p.129 / Chapter 4.5.1 --- In vitro Studies --- p.129 / Chapter 4.6 --- References --- p.131 / Appendix --- p.135

Duan Lei. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2005. / Includes bibliographical references. / Abstracts in English and Chinese. / Abstract --- p.i / Abstract (in Chinese) --- p.iii / Acknowledgement --- p.iv / Table of Contents --- p.v / List of Figures --- p.viii / List of Tables --- p.xii / List of Schemes --- p.xiii / Abbreviations --- p.xvi / Chapter Chapter 1 --- Unsymmetrical Phthalocyanines 一 An Overview / Chapter 1.1 --- Introduction --- p.1 / Chapter 1.2 --- Synthesis of A3B Phthalocyanines --- p.7 / Chapter 1.2.1 --- Statistical Condensation --- p.7 / Chapter 1.2.2 --- The Subphthalocyanine Approach --- p.13 / Chapter 1.2.3 --- Synthesis on Polymer Support --- p.16 / Chapter 1.3 --- Synthesis of A2B2 Phthalocyanines --- p.18 / Chapter 1.3.1 --- Preparation of Cross-Substituted Phthalocyanines (ABAB-type) --- p.19 / Chapter 1.3.2 --- Preparation of ´ب´بAdjacent´ح Phthalocyanines (AABB-type) --- p.21 / Chapter 1.4 --- Objectives of This Thesis --- p.24 / Chapter 1.5 --- References --- p.25 / Chapter Chapter 2 --- "Synthesis, Characterization and in vitro Photodynamic Activities of Mono-Alkoxy and Hydroxy Zinc(II) Phthalocyanines" / Chapter 2.1 --- Introduction --- p.29 / Chapter 2.2 --- "Preparation and Characterization of Unsymmetrical Zinc(II) Phthalocyanines Substituted with a 3,4,5- Tris(dodecyloxy)phenylmethyloxy Group" --- p.30 / Chapter 2.3 --- Preparation and Characterization of Halogenated Unsymmetrical Zinc(II) Phthalocyanines --- p.35 / Chapter 2.4 --- Preparation and Characterization of 2-Hydroxy Zinc(II) Phthalocyanine --- p.44 / Chapter 2.5 --- Introduction of Photodynamic Therapy (PDT) --- p.47 / Chapter 2.6 --- In vitro Photodynamic Activities of 2-Hydroxy Zinc(II) Phthalocyanine --- p.50 / Chapter 2.7 --- Conclusion --- p.52 / Chapter 2.8 --- Experimental Section --- p.52 / Chapter 2.9 --- References --- p.63 / Chapter Chapter 3 --- "Synthesis, Characterization and in vitro Photodynamic Activities of Phthalocyanines Containing N，N-Di- methylaminoethylsulfanyl Substituents" / Chapter 3.1 --- Introduction --- p.66 / Chapter 3.2 --- Preparation and Characterization of Octasubstituted Phthalocyanines --- p.67 / Chapter 3.3 --- Characterization of Disubstituted Amphiphilic Zinc(II) Phthalocyanines --- p.74 / Chapter 3.4 --- In vitro Photodynamic Activities --- p.80 / Chapter 3.5 --- Conclusion --- p.83 / Chapter 3.6 --- References --- p.90

Chapter 1 presents an overview of the synthetic methods and properties of phthalocyanines, focusing on the unsymmetrical analogues, side-strapped derivatives, and crown ether-containing phthalocyanines. The use of these compounds in photodynamic therapy and their supramolecular chemistry are also reviewed. / Chapter 2 reports the synthesis of a series of unsymmetrical "3+1" zinc(II) phthalocyanines via a one-pot cyclization-transesterification procedure in different alcoholic solvents. Their photophysical properties and in vitro photodynamic activities toward HT29 human colorectal adenocarcinoma cells and HepG2 human hepatocarcinoma cells are also reported. One of the compounds, a zinc(II) phthalocyanine substituted with two polyethylene glycol chains, can form surfactant-free nanoparticles in water and in the culture media. These phthalocyanine-containing nanoparticles exhibit a high photocytotoxicity toward HepG2 cells showing that the polymeric substituents may serve as an effective carrier system. / Chapter 4 reports the synthesis and spectroscopic properties of a side-strapped bis(17-crown-5)-containing zinc(II) phthalocyanine. In contrast to the previously reported benzo-fused crown ether-appended phthalocyanines, the ether rings of this molecule are orthogonal to the phthalocyanine plane. As a result, this compound forms J-aggregate in chloroform. Upon addition of alkali metal ions, these aggregates are disrupted forming a linear supramolecular structure, which has been inferred by absorption and fluorescence spectroscopic methods. / Chapter 5 describes the synthesis and spectroscopic properties of two side-strapped zinc(II) phthalocyanines, which have one and two benzo-25-crown-8 moieties, respectively. The bis(crown ether) analogue favors the formation of J-aggregate in non-coordinating solvents. In CHCl 3, the aggregation of these compounds is promoted by the addition of 1,2-bis(pyridinium)ethane bis(hexfluorophosphate). The aggregation of these compounds can also be induced by the oxonium ions generated by the addition of organic acids such as trifluoroacetic acid and acetic acid. After neutralization with Et3N, the aggregate is disrupted and the phthalocyanines are converted back to their original nonaggregated state. For the symmetrically substituted compound, this acid-base switched aggregation-disaggregation process can be recycled for more than 8 times. / The synthesis, spectroscopic characterization, photophysical properties, aggregation properties, and in vitro photodynamic activities of several side-strapped phthalocyanines are described in Chapter 3. Pentaerythritol, having four hydroxyl groups, has been used as the linker to connect hydrophilic oligoethylene glycol chains or hydrophobic alkyl chains to the phthalocyanine core. The aggregation tendency of these compounds, which depends on their amphiphility, has been studied by absorption spectroscopy. The relationship of this property with the in vitro photocytotoxicity has also been revealed. / This thesis reports our studies on several novel series of phthalocyanines including a series of "3+1" unsymmetrical phthalocyanines formed by a one-pot cyclization-transesterification procedure, and several side-strapped phthalocyanines having an amphiphilic character or containing crown ether units. The applications of these compounds in photodynamic therapy and supramolecular chemistry have also been explored. / by Bai, Ming. / "September 2007." / Source: Dissertation Abstracts International, Volume: 69-08, Section: B, page: 4745. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2007. / Includes bibliographical references. / 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, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese. / School code: 1307.

A novel series of silicon(IV) phthalocyanines substituted axially with one or two 1,3-bis(dimethylamino)-2-propoxy group(s) are described in Chapter 3. These compounds are essentially non-aggregated in common organic solvents and show a weak fluorescence emission, while their methylated derivatives are also non-aggregated even in aqueous media and exhibit a strong fluorescence emission. The photocytotoxicities of these compounds against HepG2 and J774 cells have also been investigated. These new phthalocyanines, in particular the unsymmetrical and amphiphilic analogues, are highly potent with IC50 values down to 20 nM. The cellular uptake and subcellular localisation of these compounds have also been studied by fluorescence microscopy. The unsymmetric phthalocyanine SiPc[OC3H5(NMe2 )2](OMe) has a high and selective affinity to the mitochondria of HepG2 cells. / Chapter 1 presents an overview of photodynamic therapy, including its historical development, current clinical status, and photophysical and biological mechanisms. Some representative photosensitisers are also reviewed. / Chapter 2 describes two silicon(IV) phthalocyanines containing poly(ethylene glycol) chains at the axial positions, including their synthesis, spectroscopic characteristics and photophysical properties. Their complexation with bovine serum albumin and in vitro photodynamic activities towards HepG2 human hepatocarcinoma cells and J774 mouse macrophage are also reported. / Chapter 4 discusses the photodynamic effects of a series of silicon(IV) phthalocyanines with different axial substituents against HT29 and T84 human colon adenocarcinoma cells, with the long-term goal of developing efficient photosensitising agents for colorectal cancer. While these compounds are not cytotoxic in the absence of light, they exhibit high photocytotoxicities with IC50 values as low as 17 nM. / Chapter 5 reports the synthesis and characterisation of a series of halogenated silicon(IV) phthalocyanines substituted axially with poly(ethylene glycol), 1,3-bis(dimethylamino)-2-propoxy or isopropylidene-protected galactose groups, with the goal of enhancing the photosensitising properties by heavy atom effect. (Abstract shortened by UMI.) / This thesis describes the synthesis, spectroscopic characterisation, and photo-physical and biological properties of a series of novel silicon(IV) phthalocyanines which are potentially useful as second-generation photosensitisers for photodynamic therapy. / Lo Pui-chi. / "September 2005." / Adviser: Dennis K. P. Ng. / Source: Dissertation Abstracts International, Volume: 67-07, Section: B, page: 3813. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2005. / Includes bibliographical references. / 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, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstract in English and Chinese. / School code: 1307.

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