Penelope J. Brothers is Director of the Research School of Chemistry at the Australian National University, and Honorary Professor at the School of Chemical Sciences at the University of Auckland in New Zealand.Mathias O. Senge, is Professor and Chair of Organic Chemistry at Trinity College Dublin and Hans Fischer Senior Fellow at the Institute of Advanced Study of the Technical University Munich.

• Volume 1List of Contributors xiii1 An Introduction to Porphyrins for the Twenty-First Century 1Penelope J. Brothers and Mathias O. Senge1.1 Why Porphyrins? 11.2 The Natural World of Porphyrins 31.3 Brief History of Porphyrins 41.4 Practical Applications 51.5 Porphyrins for the Twenty-First Century 72 It's All in the Name 9Mathias O. Senge2.1 Basic Structure and Nomenclature of Porphyrins 92.2 General Classes of Porphyrin Systems 112.3 Naturally Occurring Porphyrins 152.4 Special Aspects of Porphyrin Nomenclature 242.5 Porphyrin Stenography 303 Organic Synthesis and Reactivity of Porphyrins 37Mathias O. Senge and Alina Meindl3.1 Introduction 373.2 Synthesis of meso-Substituted Porphyrins from Pyrrole Building Blocks 393.3 Synthesis of Β-Substituted Porphyrins from Pyrrole Building Blocks 523.4 Total Synthesis of Other Porphyrin(oid)s 573.5 Reactivity of Porphyrins 663.6 Transition-Metal-Catalyzed Reactions at the Porphyrin Macrocycle 793.7 Peripheral Functionalization 913.8 Examples of Classic and Contemporary Target Systems 1034 Coordination Chemistry 141Penelope J. Brothers and Abhik Ghosh4.1 Introduction 1424.2 Overview of the Coordination Chemistry of Porphyrin and its Analogues 1434.3 Metallation, Demetallation, and Characterization 1524.4 Main Group Elements 1584.5 Transition Metals 1704.6 Lanthanides and Actinides 1974.7 Organometallic Porphyrin Complexes 2045 Phthalocyanines and Porphyrazines 241Ümit Isci and Fabienne Dumoulin5.1 Phthalocyanines and Porphyrazines: Structures and Syntheses of Peculiar Members of the Porphyrin Family 2415.2 Synthetic Methods and Strategies 2475.3 Preparation and Characterization of Precursors 2505.4 Formation of Macrocycles with Asymmetric Substitution Patterns 2625.5 Lanthanide Double- and Multi-Decker Derivatives 2725.6 Other Double- and Multi-Decker Derivatives 2765.7 Reactions on Phthalocyanines and Porphyrazines 2785.8 Conclusion 2896 Oxidation and Reduction of Porphyrins 303Christian Brückner and Nisansala Hewage6.1 Introduction: Scope and Limits of This Chapter 3036.2 Reductions of Porphyrins 3046.3 Oxidations of Porphyrins 3116.4 Metal-Centered and Resonance-Stabilized Π-System Redox Events 3307 Corroles and Contracted Porphyrins 349Daniel T. Gryko and Mariusz Tasior7.1 Introduction 3497.2 Corroles 3497.3 Isocorroles 3687.4 N-Confused Corroles 3697.5 Heteroanalogues of Corroles 3697.6 Norcorroles 3737.7 Outlook 3748 Heteroporphyrins and Carbaporphyrins 385Timothy D. Lash8.1 Introduction 3858.2 Mono- and Diheteroporphyrins (O, S, Se, Te) 3868.3 Tetraoxa-, Tetrathia-, and Tetraselenaporphyrin Dications 3978.4 Phosphaporphyrins 4008.5 Carbaporphyrinoid Systems 4028.6 True Carbaporphyrins 4058.7 Azuliporphyrins 4168.8 Neo-Confused Porphyrins 4278.9 Benziporphyrins 4278.10 Miscellaneous Carbaporphyrinoid Systems 4348.11 Dicarbaporphyrinoids 4398.12 Tetracarbaporphyrinoids 4458.13 Related Porphyrin Analogues 4478.14 Conclusions 4489 Expanded Porphyrins 453Atsuhiro Osuka and Takayuki Tanaka9.1 Historical Background 4539.2 One-Pot Synthesis of Expanded Porphyrins 4559.3 Size-Selective Syntheses of Expanded Porphyrins 4619.4 Möbius Aromatic Expanded Porphyrins 4669.5 Giant Expanded Porphyrins 471References 473Volume 2List of Contributors xiii10 Fundamentals of Porphyrin and Metalloporphyrin Stereochemistry 479W. Robert Scheidt11 Porphyrins: Electronic Structure and Ultraviolet/Visible Absorption Spectroscopy 505M. Cather Simpson and Nina I. Novikova12 Photoinduced Electron and Energy Transfer 587Eugeny A. Ermilov and Beate Röder13 NMR Spectroscopy of Porphyrins 611Craig J. Medforth14 Spin States in Iron Porphyrins 631Mikio Nakamura15 Electrochemical Properties of Porphyrin-Type Complexes 661Tebello Nyokong16 Heme Proteins -- Structure and Function 709Sk Amanullah, Chandradeep Ghosh, Somdatta Ghosh Dey and Abhishek Dey17 Chlorophylls 743Hitoshi Tamiaki18 Vitamin B12 and Cofactor F430 777Bernhard Kräutler and Bernhard M. JaunIndex 815

Penelope J. Brothers is Director of the Research School of Chemistry at the Australian National University, and Honorary Professor at the School of Chemical Sciences at the University of Auckland in New Zealand.Mathias O. Senge, is Professor and Chair of Organic Chemistry at Trinity College Dublin and Hans Fischer Senior Fellow at the Institute of Advanced Study of the Technical University Munich.

• Volume 1List of Contributors xiii1 An Introduction to Porphyrins for the Twenty-First Century 1Penelope J. Brothers and Mathias O. Senge1.1 Why Porphyrins? 11.2 The Natural World of Porphyrins 31.3 Brief History of Porphyrins 41.4 Practical Applications 51.5 Porphyrins for the Twenty-First Century 72 It's All in the Name 9Mathias O. Senge2.1 Basic Structure and Nomenclature of Porphyrins 92.2 General Classes of Porphyrin Systems 112.3 Naturally Occurring Porphyrins 152.4 Special Aspects of Porphyrin Nomenclature 242.5 Porphyrin Stenography 303 Organic Synthesis and Reactivity of Porphyrins 37Mathias O. Senge and Alina Meindl3.1 Introduction 373.2 Synthesis of meso-Substituted Porphyrins from Pyrrole Building Blocks 393.3 Synthesis of Β-Substituted Porphyrins from Pyrrole Building Blocks 523.4 Total Synthesis of Other Porphyrin(oid)s 573.5 Reactivity of Porphyrins 663.6 Transition-Metal-Catalyzed Reactions at the Porphyrin Macrocycle 793.7 Peripheral Functionalization 913.8 Examples of Classic and Contemporary Target Systems 1034 Coordination Chemistry 141Penelope J. Brothers and Abhik Ghosh4.1 Introduction 1424.2 Overview of the Coordination Chemistry of Porphyrin and its Analogues 1434.3 Metallation, Demetallation, and Characterization 1524.4 Main Group Elements 1584.5 Transition Metals 1704.6 Lanthanides and Actinides 1974.7 Organometallic Porphyrin Complexes 2045 Phthalocyanines and Porphyrazines 241Ümit Isci and Fabienne Dumoulin5.1 Phthalocyanines and Porphyrazines: Structures and Syntheses of Peculiar Members of the Porphyrin Family 2415.2 Synthetic Methods and Strategies 2475.3 Preparation and Characterization of Precursors 2505.4 Formation of Macrocycles with Asymmetric Substitution Patterns 2625.5 Lanthanide Double- and Multi-Decker Derivatives 2725.6 Other Double- and Multi-Decker Derivatives 2765.7 Reactions on Phthalocyanines and Porphyrazines 2785.8 Conclusion 2896 Oxidation and Reduction of Porphyrins 303Christian Brückner and Nisansala Hewage6.1 Introduction: Scope and Limits of This Chapter 3036.2 Reductions of Porphyrins 3046.3 Oxidations of Porphyrins 3116.4 Metal-Centered and Resonance-Stabilized Π-System Redox Events 3307 Corroles and Contracted Porphyrins 349Daniel T. Gryko and Mariusz Tasior7.1 Introduction 3497.2 Corroles 3497.3 Isocorroles 3687.4 N-Confused Corroles 3697.5 Heteroanalogues of Corroles 3697.6 Norcorroles 3737.7 Outlook 3748 Heteroporphyrins and Carbaporphyrins 385Timothy D. Lash8.1 Introduction 3858.2 Mono- and Diheteroporphyrins (O, S, Se, Te) 3868.3 Tetraoxa-, Tetrathia-, and Tetraselenaporphyrin Dications 3978.4 Phosphaporphyrins 4008.5 Carbaporphyrinoid Systems 4028.6 True Carbaporphyrins 4058.7 Azuliporphyrins 4168.8 Neo-Confused Porphyrins 4278.9 Benziporphyrins 4278.10 Miscellaneous Carbaporphyrinoid Systems 4348.11 Dicarbaporphyrinoids 4398.12 Tetracarbaporphyrinoids 4458.13 Related Porphyrin Analogues 4478.14 Conclusions 4489 Expanded Porphyrins 453Atsuhiro Osuka and Takayuki Tanaka9.1 Historical Background 4539.2 One-Pot Synthesis of Expanded Porphyrins 4559.3 Size-Selective Syntheses of Expanded Porphyrins 4619.4 Möbius Aromatic Expanded Porphyrins 4669.5 Giant Expanded Porphyrins 471References 473Volume 2List of Contributors xiii10 Fundamentals of Porphyrin and Metalloporphyrin Stereochemistry 479W. Robert Scheidt11 Porphyrins: Electronic Structure and Ultraviolet/Visible Absorption Spectroscopy 505M. Cather Simpson and Nina I. Novikova12 Photoinduced Electron and Energy Transfer 587Eugeny A. Ermilov and Beate Röder13 NMR Spectroscopy of Porphyrins 611Craig J. Medforth14 Spin States in Iron Porphyrins 631Mikio Nakamura15 Electrochemical Properties of Porphyrin-Type Complexes 661Tebello Nyokong16 Heme Proteins -- Structure and Function 709Sk Amanullah, Chandradeep Ghosh, Somdatta Ghosh Dey and Abhishek Dey17 Chlorophylls 743Hitoshi Tamiaki18 Vitamin B12 and Cofactor F430 777Bernhard Kräutler and Bernhard M. JaunIndex 815