Applications of Porphyrinoids as Functional Materials

Cover
Preface
Contents
Chapter 1 Fundamentals and Applications in Solution-phase Electrochemistry and Electrocatalysis
1.1 Introduction
1.2 Fundamentals of Solution-phase Voltammetry
1.3 Examples of Solution-phase Voltammetry Studies
1.3.1 The Gap Between Benzoporphyrins and Phthalocyanines
1.3.2 Electronic Communication Between Ring Substituents Illustrated
1.3.3 Electronic Communication with Axial Ligands
1.3.4 Observation of 17 Redox Processes for a Triple-decker Porphyrinoid
1.3.5 Solution-phase Outer-sphere Electron Transfer and Reference Potentials
1.3.6 Effect of Non-specific and Specific Adsorption on CVs
1.3.7 Inner-sphere Electron Transfer Occurs for Adsorbed Species
1.3.8 Dependence of Peak Currents on Scan Rates
1.4 Electrocatalysis: Some Fundamental Concepts
1.5 Examples of Electrocatalysis Studies
1.5.1 Easing into the Concepts: Ni(OH)2-electrocatalyzed Alcohol Oxidation
1.5.2 The Importance of Confirming an Electrode Is Not the Active Catalyst
1.5.3 The Quest for Strong Electrode-electrocatalyst Interactions
1.5.4 Sulfite Sensing by Adsorbed Ladder Cobalt Porphyrin Polymers
1.6 Electrocatalysts Important for Fuel Production and Energy Storage
1.6.1 CO2 Reduction Electrocatalyzed by Solution-based Fe0TPP in Ionic Liquids
1.6.2 H2 Evolution from H1 Catalyzed by Pyrrole Ring-modified Ni Porphyrins
1.6.3 Oxygen Reduction Catalyzed by Ferrocenyl-substituted Co Porphyrins
1.6.4 Oxidation of Water to Oxygen Catalyzed by Porphyrinoids
1.6.5 Octa-alkoxylated CoPcs Aggregate Less, Better Catalysis
1.6.6 CODs and MOFs Improve Electrocatalysis by Porphyrinoids
1.7 Conclusions
Acknowledgements
References
Chapter 2 Electrochemistry-driven Electron-transfer Processes in Porphyrinoids
2.1 Introduction
2.2 Overview of the Electrochemistry of Porphyrins and Their Analogs
2.2.1 Metal-free and Central-metal Redox-inert Metalloporphyrins and Their Analogs
2.2.2 Metalloporphyrins and Their Analogs with Redox-active Central Metal Ions
2.2.3 Electrochemistry of Porphyrinoids with Redox-active Substituents or Axial Ligands
2.3 Overview of the Spectroscopy of the Redox-active Forms in Porphyrinoids
2.3.1 Ligand-centered Processes
2.3.2 Metal-centered Processes
2.3.3 Substituent(s) or Axial Ligand(s)-centered Processes
2.4 Redox-driven Applications of the Porphyrinoids
2.5 Conclusions
References
Chapter 3 Porphyrinoids as Active Masses in Electrochemical Energy Storage
3.1 Introduction and Background
3.2 Use in Secondary Batteries
3.3 Use in Supercapacitors
3.4 Use in Redox Flow Batteries
3.5 Use as Auxiliary Material
3.6 Miscellaneous Observations
Acknowledgements
References
Chapter 4 Self-assembly on Crystalline Surfaces: From Phthalocyanines to Porphyrins
4.1 Introduction
4.2 Phthalocyanines
4.2.1 Phthalocyanine Monolayers on Highly-oriented Pyrolytic Graphite
4.2.2 Phthalocyanine Monolayers on Noble Metal Substrates
4.3 Porphyrins
4.3.1 Porphyrin Monolayers on Noble Metal Substrates
4.4 Summary
Acknowledgements
References
Chapter 5 Chemical Vapor Deposition of Porphyrins
5.1 Introduction
5.2 Vapor Phase Transport of Porphyrins
5.3 Plasma-polymerization of Porphyrins
Chemical Vapor Deposition
5.3.1 Plasma-enhanced Chemical Vapor Deposition of Porphyrins
5.3.2 Porphyrin-based Plasma Polymer Thin Films for Gas Sensing
5.4 Free-radical Polymerization of Porphyrins via
Chemical Vapor Deposition
5.4.1 Initiated Plasma Enhanced Chemical Vapor Deposition of Porphyrins
5.4.2 Poly(Porphyrin) Thin Films for Gas Separation
5.5 Dehydrogenative Coupling of Porphyrins
5.5 Dehydrogenative Coupling of Porphyrins via
Chemical Vapor Deposition
5.5.1 Oxidative Chemical Vapor Deposition of Fused Porphyrin Tape Thin Films
5.5.2 Fused Porphyrin Tape Thin Films for Electronic Gas Sensing
5.5.3 Fused Porphyrin Tape Thin Films for Heterogeneous Catalysis
5.6 Summary
References
Chapter 6 Liquid Crystalline Phthalocyanines
6.1 Overview of Liquid Crystals
6.2 Various Molecular Structures of Phthalocyaninebased Liquid Crystals
6.3 Unique Molecular Structures and Mesophase Structures
6.3.1 Flying-seed-like Liquid Crystals
6.3.2 Helical Structures by Vortex
6.3.3 Spiranthes-like Supramolecular Structure of Liquid-crystalline PcC60 Dyads
References
Chapter 7 Recent Progress in Porphyrin Derivatives Used in Organic Thin-film Solar Cells
7.1 Introduction
7.2 Porphyrin Derivatives with Donor–Acceptor Structures
7.3 Porphyrin Dimers for Donor Materials
7.4 Combination of Porphyrin Derivatives and Nonfullerene Acceptors
7.5 Application of Porphyrin Derivatives to Acceptor Materials
7.6 Concluding Remarks
References
Chapter 8 Photophysical Characterization of Porphyrinoids
8.1 Introduction
8.2 Photophysical Characterization: Basics
8.3 Photophysical Properties of Porphyrinoids
8.3.1 Porphyrins
8.3.2 Chlorin
8.3.3 Bacteriochlorin
8.3.4 Corroles
8.3.5 Tetrabenzoporphyrins
8.3.6 Porphyrazines
8.3.7 Phthalocyanines
8.3.8 Naphthalocyanines
8.3.9 Azulenocyanines
8.4 Conclusion
References
Chapter 9 Porphyrinoids for Photodynamic Therapy
9.1 Introduction
9.2 Historical Overview of Phototherapy
9.2.1 Early Development and Advances in Photodynamic Therapy
9.3 Porphyrinoids in Phototherapy
9.3.1 Mechanism of Photodynamic Therapy and Photosensitizers
9.3.2 Photophysical Aspects of PDT
9.3.3 Photopharmacological Aspects of Photodynamic Therapy
9.4 Photodynamic Therapy and Cancer–Clinical Applications
9.4.1 Clinically Approved Photosensitizers
9.4.2 Photosensitizers Under Development
9.5 Strategies for Improvement of Photosensitizers
9.5.1 Modulation of the Photophysical Properties
9.5.2 Photosensitizer Uptake and Cellular Localization
9.5.3 Targeted Photodynamic Therapy and Nano-approaches
9.6 Conclusion
Acknowledgements
References
Chapter 10 Porphyrins and Hydroporphyrins for In Vivo Bioimaging
10.1 Introduction
10.2 Tailoring Porphyrin Optical Properties for In Vivo Fluorescence Imaging
10.3 Tetrapyrrolic Macrocycles in Fluorescence In Vivo Imaging
10.3.1 Simple Porphyrins for In Vivo Fluorescence Imaging
10.3.2 Benzoporphyrins for In Vivo Oxygen Sensing
10.3.3 In Vivo Imaging by Strongly Conjugated Porphyrin Arrays
10.3.4 In Vivo Fluorescence Imaging of Cancer by Semi-synthetic Chlorins and Bacteriochlorins
10.3.4 In Vivo Fluorescence Imaging of Cancer by
Semi-synthetic Chlorins and Bacteriochlorins
10.3.5 Synthetic Hydroporphyrins as Activatable and Targetable Probes for Cancer Imaging
10.3.6 Hydroporphyrin Energy-transfer Arrays for In Vivo
Imaging
10.3.7 Porphyrin and Porpholactone Lanthanides Complexes
for In Vivo Imaging
10.4 Nanomaterials Composed of Hydroporphyrins
for In Vivo Imaging
10.5 Summary
Acknowledgements
References
Chapter 11 Porphyrinoids in Association with Nanomaterials for Water Purification
11.1 Introduction
11.2 Applications of Porphyrinoids
11.2.1 Water Purification
11.2.2 Nanoscale Advancements in the Microbial Photodynamic Inactivation (aPDI)
11.2.3 Application of Conjugated Porphyrins and Nanomaterials in Water Treatment
11.2.4 Electrochemical Behavior of Porphyrins—Ion Trapping
11.2.5 Porphyrinoids as Ionophores
11.3 Perspective and Outlook
References
Chapter 12 Porphyrinoids Used for Photodynamic Inactivation against Bacteria
12.1 Introduction
12.2 Photosensitizers in Photodynamic Antimicrobial Chemotherapy
12.2.1 Porphyrin Derivatives
12.2.2 Chlorin Derivatives
12.2.3 Phthalocyanine Derivatives
12.3 Nanoparticles–porphyrinoid Combinations against Bacteria
12.3.1 Silver Nanoparticles (AgNPs)
12.3.2 Gold Nanoparticles (AuNPs)
12.3.3 Titanium Oxide Nanoparticles (TiO2 NPs)
12.4 Clinical Potential of Porphyrinoids Against Infections
12.4.1 Acne Vulgaris
12.4.2 Dentistry
12.4.3 Blood Products Disinfection
12.4.4 Self-sterilization Materials
12.5 Porphyrinoids in Combination with Antibiotics Against Bacteria
12.6 Concluding Remarks
References
Chapter 13 Applicability of Highly Functional Phthalogens
13.1 Introduction
13.2 Synthesis and Characterization of Phthalogens
13.2.1 ‘‘Box’’-type Phthalogens
13.2.2 Hexa-dentate ‘‘Helmet’’-type Phthalogens
13.2.3 Penta-dentate ‘‘Helmet’’-type Phthalogens
13.2.4 Alkoxy-substituted ‘‘Antenna’’-type Phthalogens
13.2.5 Phthalogens – Formation Mechanism
13.3 Application of Phthalogens
13.3.1 Optical Spectra and Thermal Stability Phenomena
13.3.2 Fiber Coloring – Redox Properties
13.3.3 Chirality and Homogeneous Catalysis
13.4 Conclusions
Acknowledgements
References
Subject Index