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At the end of this thesis, selected 1H NMR spectra and crystallographic data are given as an Appendix. / Chapter 1 presents an overview of supramolecular chemistry and the general properties of phthalocyanines, focusing on the self-assembly of mixed porphyrin and phthalocyanine systems. / Chapter 2 describes the complexation of bis(pyridinolato) silicon(IV) phthalocyanines to several cobalt(II) porphyrins. As shown by absorption spectroscopy, both 1:1 and 1:2 molecular assemblies can be obtained depending on the relative amount of the two components and the position of the pyridyl ligand. The axially bound 1:1 phthalocyanine-porphyrin arrays have also been isolated and characterized spectroscopically. / Chapter 3 reports an extension of this work. Two novel phthalocyanines with 3 or 4 pyridyl axial substituents have been synthesized. These compounds bind to meso-tetraphenyl zinc porphyrin to form the corresponding tetrakis- and pentakis-mixed tetrapyrrole systems. / Chapter 4 discusses the preparation of several covalently-linked phthalocyanine-cyclodextrin conjugates. These compounds can form inclusion complexes with sulfonated porphyrin in water providing a new strategy to construct mixed phthalocyanine and porphyrin systems. / Chapter 5 reports the interactions of two octacarboxy phthalocyanines with beta-cyclodextrin. Through the formation of inclusion complexes, the latter serves as a disstacking agent reducing the aggregation tendency of these phthalocyanines. This supramolecular approach could be an effective way to generate hydrophilic and non-aggregated phthalocyanines, improving their photosensitising properties in aqueous media. / This thesis reports our investigation on the supramolecular chemistry of phthalocyanines. The first part of the thesis describes the self-assembly of mixed porphyrin and phthalocyanine systems through axial coordination. The second part complexes between phthalocyanines and reports the formation of some novel inclusion phthalocyanine-cyclodextrin conjugates and porphyrins, beta-cyclodextrin. / Leng, Xuebing. / "March 2007." / Adviser: Dennis K. P. Ng. / Source: Dissertation Abstracts International, Volume: 68-09, Section: B, page: 5946. / 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. / Abstract in English and Chinese. / School code: 1307.

by Ka-Wo Poon. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1999. / Includes bibliographical references (leaves 113-120). / Abstracts in English and Chinese. / ABSTRACT --- p.i / ACKNOWLEDGMENT --- p.iii / CONTENTS --- p.iv / LIST OF FIGURES --- p.vi / LIST OF TABLES --- p.x / ABBREVIATIONS --- p.xi / Chapter 1. --- INTRODUCTION --- p.1 / Chapter 1.1 --- General Background of Tetrapyrrole Derivatives --- p.1 / Chapter 1.2 --- Electronic Interactions in Systems with Multiple Redox Sites --- p.8 / Chapter 1.2.1 --- Electronic Interactions in One-dimensional Systems --- p.9 / Chapter 1.2.2 --- Electronic Interactions in Three-dimensional Systems --- p.12 / Chapter 1.3 --- Ferrocene-containing Tetrapyrrole Derivatives --- p.22 / Chapter 1.3.1 --- Ferrocene-containing Porphyrins --- p.22 / Chapter 1.3.2 --- Ferrocene-containing Porphyrazines --- p.29 / Chapter 1.3.3 --- Ferrocene-containing Phthalocyanines --- p.30 / Chapter 2. --- RESULTS AND DISCUSSION --- p.38 / Chapter 2.1 --- Ferrocenylphthalocyanines with Oxyethylene Linkers --- p.38 / Chapter 2.1.1 --- Synthesis and Characterization --- p.38 / Chapter 2.1.1.1 --- Preparation of Tetrakis(2-ferrocenylethoxy)- phthalocyaninatozinc(II) (55) --- p.38 / Chapter 2.1.1.2 --- Preparation of Octakis(2-ferrocenylethoxy)- phthalocyaninatozinc(II) (62) --- p.43 / Chapter 2.1.1.3 --- Preparation of Metal Free Hexadecakis(2- ferrocenylethoxy)phthalocyanine (65) --- p.49 / Chapter 2.1.2 --- Electronic Absorption Spectra --- p.52 / Chapter 2.1.3 --- Electrochemical Studies --- p.60 / Chapter 2.2 --- Ferrocenyl Tetrapyrroles with Ethynyl Linkers --- p.68 / Chapter 2.2.1 --- Synthesis and Characterization --- p.68 / Chapter 2.2.1.1 --- Preparation of Octakis(ferrocenylethynyl)- phthalocyaninatozinc(II) (83) --- p.71 / Chapter 2.2.1.2 --- Preparation of Octakis(ferrocenylethynyl)- Naphthalocyaninatozinc(II) (87) --- p.76 / Chapter 2.2.1.3 --- "Preparation of 5,15-bis(ferrocenylethynyl)- 10,20-diphenylporphyrinatonickel(II) (90)" --- p.81 / Chapter 2.2.2 --- Electrochemical Studies --- p.84 / Chapter 2.3 --- Conclusion --- p.92 / Chapter 3. --- EXPERIMENTAL SECTION --- p.93 / Chapter 3.1 --- General Methods --- p.93 / Chapter 3.2 --- Physical Measurements --- p.93 / Chapter 3.3 --- Synthesis of Ferrocenylphthalocyanines with Oxyethylene Linkers --- p.95 / Chapter 3.4 --- Synthesis of Ferrocenyl Tetrapyrrole Derivatives with Ethynyl Linkers --- p.105 / Chapter 4. --- REFERENCES --- p.111 / Chapter APPENDIX A --- 1H NMR spectra of dinitriles --- p.121 / Chapter APPENDIX B --- 13C̐ưث1H }NMR spectra of dinitriles --- p.126

by Choi, Chi Fung. / "September 2007." / 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. / 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.

"December 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.

This project was focused on the synthesis of novel phthalocyanines for the construction of porous molecular crystals that incorporate the desirable properties associated with phthalocyanine complexes. Conventional phthalocyanines are relatively insoluble, therefore, remain difficult to process, characterise and effectively crystallise. To counteract this problem, bulky 2,6-di-iso-propylphenoxy substituents were placed around the aromatic core of the phthalocyanine macrocycle and proved to successfully inhibit the co-facial aggregation which limits their solubility. These bulky groups also direct the crystallisation of the phthalocyanine macrocycle inducing a cubic packing arrangement with significant accessible solvent filled voids. The aim of this work was the modification of this 2,6-di-isopropylphenoxy substituted phthalocyanine to enhance the magnetic and catalytic properties and demonstrate its suitability as a platform for creating iso-reticular systems with increased functionality. It was anticipated that mixed double decker complexes of this derivative and another phthalocyanine macrocycle would form crystals with the same cubic spatial arrangement, while maintaining their high catalytic activity or single molecular magnetism behaviour. Firstly, a larger number of transition metals along with some lanthanide metals have been incorporated within this substituted phthalocyanine, extending the previous work on this system. Furthermore, the corresponding contracted macrocycle boron subphthalocyanine was also investigated. While the 2,6-diisopropylphenyl substituents did not greatly affect the electronic properties of the subphthalocyanine, the solid state properties of the material proved interesting. The lanthanide phthalocyanine complexes were further employed in the preparation of lanthanide double decker phthalocyanines that possess single molecule magnetic properties. While retaining this desired property, they also crystallised to produce clathrates with large solvent filled voids. A different double decker complex which contained two iron metal centres bridged by a single nitrogen atom was also prepared from the octa substituted 2,6-di-iso-propylphenoxy phthalocyanine and an unsubstituted phthalocyanine. This nitrido bridged di-iron phthalocyanine complex displayed similar catalytic activity to previously reported systems of this kind and crystallised to afford cubic crystals with large solvent filled voids. These were shown to be accessible by both solvent and ligand exchange. Suitable bidentate ligands for structural stabilisation could be also incorporated. Finally, the preparation of an alternatively substituted phthalocyanine for the construction of a potential porous molecular crystal was studied. By synthesising a hexamethylindan substituted phthalonitrile, it was possible to obtain a soluble phthalocyanine that crystallised to give a clathrate that contained large one-dimensional voids.

Thesis (M. Phil.)--University of Hong Kong, 2002. / Includes bibliographical references (leaves 97-102).

Thesis (M. Phil.)--Hong Kong University of Science and Technology, 2003. / Includes bibliographical references (leaves 126-131). Also available in electronic version. Access restricted to campus users.

published_or_final_version / Chemistry / Doctoral / Doctor of Philosophy