Preface |
Part I Synthesis and Characterization of Porphyrins and Phthalocyanines |
Chapter 1 Preparation of Porphyrins and Phthalocyanines |
1.1 General Methods for Preparation of Porphyrins 3 |
1.1.1 Synthesis of porphyrins from natural heme 3 |
1.1.2 Synthesis of alkyl-substituted porphyrins 5 |
1.1.3 Synthesis of meso-tetraphenylporphyrins 6 |
1.1.4 Synthesis of water-soluble porphyrins 6 |
1.1.5 Synthesis of metalloporphyrins 7 |
1.1.6 Synthesis of chlorin and its derivatives 8 |
1.2 General Methods for Preparation of Phthalocyanines 9 |
1.2.1 Synthesis of water-soluble phthalocyanines 10 |
1.2.2 Synthesis of metallophthalocyanines 10 |
1.3 New Porphyrins and Phthalocyanines 12 |
1.3.1 Viologen-linked porphyrins 12 |
1.3.2 Quinone-linked porphyrins 24 |
1.3.3 Pyromellitimide-linked porphyrins 29 |
1.3.4 Carotene-linked porphyrins 31 |
1.3.5 Fullerene-linked porphyrins 34 |
1.3.6 New phthalocyanines 37 |
References 42 |
Chapter 2 Characterization of Porphyrins and Phthalocyanines |
2.1 Optical Properties 45 |
2.2 Photophysical Properties of the Photoexcited State 46 |
2.3 Photochemical Reactions of Excited States 52 |
2.4 Techniques for the Study of Excited States and Photoreactions 53 |
References 58 |
Part II Application of Porphyrins and Phthalocyanines |
Chapter 3 Photoinduced Hydrogen Evolution |
3.1 General Introduction to Photoinduced Hydrogen Evolution 65 |
3.2 Photoinduced Cleavage of Water 66 |
3.3 Photoinduced Hydrogen Evolution in Homogeneous Fourcomponent Systems 69 |
3.3.1 Bipyridinium compounds as electron carriers 73 |
3.3.2 Cytochrome C3 as an electron carriers 97 |
3.3.3 Reduction of NADP 98 |
3.3.4 Effect of micelles 101 |
3.4 Intramolecular Electron Transfer in Acceptor-linked Porphyrins and Phthalocyanines 107 |
3.4.1 Quinone-linked porphyrins 108 |
3.4.2 Pyromellitimide-linked porphyrins 112 |
3.4.3 Fullerene (C60)-linked porphyrins 114 |
3.4.4 Viologen-linked porphyrins 117 |
3.4.5 Acceptor-linked phthalocyanines 134 |
3.5 Photoinduced Hydrogen Evolution with Viologen-linked Porphyrins 135 |
3.5.1 Application of phthalocyanines 142 |
References 145 |
Chapter 4 Optical Sensors |
4.1 Fundamental Aspects of Optical Oxygen Sensors 151 |
4.2 Phosphorescence Quenching-based Sensors 154 |
4.3 Fluorescence Quenching-based Sensors Using Metallophthalocyanine 164 |
4.4 Luminescence Lifetime-based Sensors 168 |
4.5 Oxygen Sensing System by Triplet-Triplet Absorption of Porphyrins 170 |
4.6 Oxygen Monitoring in Living Cells by Palladium Porphyrin 175 |
4.7 Application of the Optical Oxygen Sensor to the Aerodynamics Field 177 |
References 183 |
Chapter 5 Sensitizers for Photodynamic Therapy |
5.1 Introduction to Photodynamic Therapy (PDT) 187 |
5.1.1 Method of PDT 188 |
5.1.2 Reaction mechanisms of PDT 189 |
5.1.3 Photosensitizers 191 |
5.2 Porphyrins for PDT 193 |
5.2.1 Porphyrins oligomer 194 |
5.2.2 Zincphyrin 196 |
5.3 Phthalocyanines for PDT 197 |
5.3.1 Zinc-sulfophthalocyanines 199 |
5.3.2 New phthalocyanines for PDT 203 |
5.4 Fluorescent Compounds in Tumor Cells 213 |
5.4.1 Fluorescence from human abdominal cancer 213 |
5.4.2 Fluorescence from solid tumor of mice 215 |
5.4.3 Fluorescence from blood of tumor-implanted mouse 216 |
5.4.4 Fluorescence from cultivated HeLa cells 217 |
5.4.5 Reaction mechanism of the formation of protoporphyrin and coproporphyrin 219 |
5.5 5-Aminolevulinic Acid (ALA) 221 |
5.6 Antibody-photosensitizer Conjugate 228 |
References 231 |
Appendix 233 |
Color plates 237 |
Abbreviations 239 |
Index 245 |
Preface |
Part I Synthesis and Characterization of Porphyrins and Phthalocyanines |
Chapter 1 Preparation of Porphyrins and Phthalocyanines |