Ladder Polymers: Synthesis, Properties, Applications and Perspectives

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Ladder Polymers

An essential reference covering the latest research on ladder polymers

Ladder polymers are a unique macromolecular architecture, consisting of a continuous strand of fused rings in their backbones. Such distinctive structures lead to a range of interesting thermal, optical, and electronic properties and self-assembly behaviors, which have been explored for various applications.

The book Ladder Polymers: Synthesis, Properties, Applications, and Perspectives presents a collection of diverse topics in ladder polymers consisting of historical overview, state-of-the-art research and development, and potential future directions, written by leading researchers in the related fields.

The topics include:

  • Conjugated ladder polymers and graphene nanoribbons
  • Nonconjugated microporous ladder polymers or polymers of intrinsic microporosity
  • Covalent double-stranded polymers
  • Supramolecular double-helical polymers and oligomers
  • Two dimensional polymers

This book is a one-stop resource on all the critical research developments in the subject of ladder polymers for broad readership including organic, polymer, and physical chemists, materials scientists and engineers, and chemical engineers.

Author(s): Masahiko Yamaguchi, Yan Xia, Tien-Yau Luh
Publisher: Wiley-VCH
Year: 2023

Language: English
Pages: 419
City: Weinheim

Cover
Title Page
Copyright
Contents
Preface
Chapter 1 Introduction
1.1 Perspective
References
Chapter 2 Conjugated, Aromatic Ladder Polymers: From Precision Synthesis to Single Chain Spectroscopy and Strong Light‐Matter Coupling
2.1 Introduction
2.2 Methylene‐Bridged Phenylene Ladder Polymers – Ladder‐Type Poly(para‐Phenylene)s – and Related Ladder Polymers
2.3 Vinylene‐Bridged Phenylene Ladder Polymers (Polypentaphene Ladder Polymers)
2.4 Conjugated Hydrocarbon Ladder Polymers with a Polyacene Skeleton
2.5 Ethylene‐Bridged Phenylene Ladder Polymers
2.6 Optoelectronic Applications of Aromatic Ladder Polymers
2.6.1 High‐Resolution Spectroscopy of LPPP
2.6.2 LPPP as a Single‐Photon Source
2.7 Interaction of Light and Matter in the Strong‐Coupling Regime
2.8 A Primer on Exciton Polaritons in Microcavities
2.9 Exciton‐Polariton Condensation in Planar Microcavities
2.10 Example of an All‐Optical Logic Based on Polariton Condensates
2.11 Controlled Spatial Confinement of Exciton Polaritons: A Solid‐State Platform for Room‐Temperature Quantum Simulators
2.12 Summary and Outlook
Acknowledgment
References
Chapter 3 Graphene Nanoribbons as Ladder Polymers – Synthetic Challenges and Components of Future Electronics
3.1 Introduction
3.2 Solution‐Based Synthesis
3.3 On‐Surface Synthesis of GNRs
3.4 Nonplanarity and Chirality
3.5 Spin Bearing GNRs and Magnetic Properties
3.6 Device Integration
3.7 Conclusion and Outlook
Acknowledgment
References
Chapter 4 Processing of Conjugated Ladder Polymers
4.1 Introduction
4.2 Solution‐Processing from Acidic Media
4.2.1 Protic Acid
4.2.2 Lewis Acid
4.3 Structural Design for Solution Processability
4.3.1 End Group Modification
4.3.2 Side‐Chain Modification
4.3.3 Nonplanar Backbone
4.4 Processing from Solution‐Dispersed Nanoparticles
4.5 In Situ Reaction
4.6 Conclusion and Outlook
References
Chapter 5 Multiporphyrin Arrays: From Biomimetics to Functional Materials
5.1 Introduction
5.2 Structure Variations and Synthetic Strategies
5.2.1 Multiporphyrin Arrays Having Linear and Ladder Shapes
5.2.2 Multiporphyrin Arrays Having Ring and Tube Shapes
5.2.3 Multiporphyrin Arrays Having Spherical Shapes
5.2.4 Multiporphyrin Arrays Having Two‐Dimensional Sheet‐Like Shapes
5.2.5 Multiporphyrin Array‐Constructed Cages
5.2.6 Multiporphyrin Array‐Based Rotaxanes
5.3 Functions and Applications
5.3.1 As Models for Studying Photochemical Processes in Natural Photosynthesis
5.3.2 As Components for Host–Guest Chemistry and Supramolecular Assemblies
5.3.3 As Porous Materials for Chemical Adsorption and Separation
5.3.4 As Catalysts for Diverse Chemical Reactions
5.4 Conclusions
References
Chapter 6 Ladder Polymers of Intrinsic Microporosity (PIMs)
6.1 Introduction
6.1.1 Porosity of PIMs
6.1.2 Thermal Stability of PIMs
6.2 Types of Ladder PIMs
6.2.1 PIM‐1
6.2.2 PIM‐1 Modification and Other Polybenzodioxane‐Based Ladder PIMs
6.2.3 Modification of PIM‐1 and Use of Different Fluorinated Monomers
6.2.4 Ladder Co‐polymers and Other Modifications
6.3 Tröger's Base PIMs (TB‐PIMs)
6.3.1 New Tröger's Base Ladder PIMs (TB‐PIMs)
6.3.2 Tröger's Base (TB) Ladder Modifications: Quaternization and Ring Opening
6.4 Applications of PIMs
6.4.1 Gas Separation
6.4.2 Gas Storage
6.4.3 Catalysis and Electrochemistry Applications
6.4.4 PIMs for Pervaporation and Nanofiltration
6.4.5 Anion and Cation Exchange and Energy Applications
6.5 Conclusions
References
Chapter 7 Catalytic Arene–Norbornene Annulation (CANAL) Polymerization for the Synthesis of Rigid Ladder Polymers
7.1 Introduction
7.2 Inspiration of CANAL Polymerization from the Catellani Reaction
7.3 CANAL Polymerization for the Synthesis of Rigid Kinked Ladder Polymers
7.4 Conclusion and Outlook
References
Chapter 8 Simultaneous Growth in Two Dimensions: A Key to Synthetic 2D Polymers
8.1 Introduction
8.2 Strategic Considerations and Some Results
8.3 On the Polymerization Mechanism
8.4 Summary
Acknowledgments
References
Chapter 9 Ladderphanes and Related Ladder Polymers
9.1 Introduction
9.2 Polynorbornene‐Based Symmetric Ladderphanes
9.2.1 General
9.2.2 Ferrocene Linkers
9.2.3 Planar Aromatic Linkers
9.2.4 Macrocyclic Metal Complexes
9.2.5 Three‐Dimensional Organic Linkers
9.3 Symmetric Ladderphanes with All Z Double Bonds on the Polymeric Backbones
9.4 Polyacetylene‐Based Ladderphanes
9.4.1 General
9.4.2 Synthesis of PA‐Based Ladderphanes
9.4.3 Charged Species in Ladderphanes and Block Ladderphanes
9.4.4 Topochemical Methods for Symmetric Ladderphanes
9.5 Unsymmetric Ladderphanes by Template Synthesis
9.5.1 General
9.5.2 Polynorbornene‐Based Unsymmetric Ladderphanes by Replication Protocol
9.6 Sequential Polymerization of a Monomer Having Two Different Polymerizable Groups
9.6.1 General
9.6.2 Polycyclobutene‐Based Unsymmetric Ladderphanes
9.7 Chemical Reactions of Ladderphanes
9.7.1 Reactions with Double Bonds on Ladderphanes
9.7.2 Reactions at the End Groups
9.7.3 Arrays of Ladderphanes
9.7.4 Cyclic Ladderphanes
9.8 Physical Properties
9.8.1 General
9.8.2 Excimer Formation and Aggregation Enhanced Excimer Emission
9.8.3 Dielectric Properties
9.9 Conclusion
References
Chapter 10 Ladder Polysiloxanes
10.1 Introduction
10.2 Preparation of LPSs
10.2.1 Hydrolysis–Condensation Procedures
10.2.2 Supramolecular Architecture‐Directed Confined Polymerization
10.3 Applications of LPSQs
10.3.1 Applications for Manufacturing Electrical Devices
10.3.2 Coatings
10.3.3 LED Encapsulants
10.3.4 Electrochromic and Electrofluorochromic Bifunctional Materials
10.3.5 Self‐Healing Polymeric Materials
10.3.6 Composite Materials
10.3.7 Fabrication of Hybrid LPSQ‐Grafted Multiwalled Carbon Nanotubes (MWNTs)
10.3.8 The Fabrication of Supermolecular Structures
10.4 Perspectives
References
Chapter 11 DNA as a Ladder Polymer, from the Basics to Structured Nanomaterials
11.1 Basics
11.1.1 Synthesis
11.1.2 Stacking Interactions
11.1.3 Sugar Packering
11.1.4 Conformations of Nucleobase
11.1.5 Hybridization and Dissociation
11.2 Noncannonical DNA Structures
11.2.1 Triple‐Stranded DNA
11.2.2 G‐Quadruplex DNA
11.2.3 Cytosine‐Rich Four Stranded DNA
11.2.4 Branched DNA
11.3 DNA Nano Assembly
11.3.1 DNA Rod‐Like 1D Wire
11.3.2 DNA Nanomaterial (DNA Origami)
11.4 Selected Examples of Biotechnology
11.4.1 Triple Helix DNA Formation with the Sequences for which the Natural Nucleotides Do Not Recognize
11.4.2 W‐shaped Nucleoside Analogs (WNAs) for TA and CG Inversion Sites
11.4.3 Pseudo‐dC Derivatives (MeAP‐ΨdC) for a CG Inversion Site
11.4.4 Base‐ and Sequence Selective RNA Modification by the Functionality Transfer Oligonucleotides
11.5 Conclusion
References
Chapter 12 Twisted Ladder Polymers: Dynamic Properties of Cylindrical Double‐Helix Oligomers with Axial Hydrophobic and Hydrophilic Groups
12.1 Ladder and Double‐Helix Polymers/Oligomers
12.2 Double‐Helix Oligomers with Long Alkyl Groups at the Axial Positions
12.2.1 Anisotropic Films Formed from Liquid Crystal Gels (LCGs)
12.2.2 Polymorphism Involving Lyotropic Liquid Crystal Gels
12.2.3 Concentric Giant Vesicle Formation
12.3 Synthesis and Properties of Long Polymethylene Compounds
12.4 Double‐Helix Oligomer Formed from Pendant Oligomer
12.5 Hydrophilic Double‐Helix Oligomers with Axial TEG Groups in Aqueous Solvents
12.5.1 Properties of Liquid Water
12.5.2 Inverse Thermoresponse of Homo‐Double‐Helix Oligomer in Aqueous Solvents
12.5.3 Inverse Thermoresponses in Different Aqueous Solvents
12.5.4 Jumps in Thermoresponse to a Small Change in Water Content
12.6 Conclusions
Acknowledgments
References
Chapter 13 Coordination Ladder Polymers: Helical Metal Strings
13.1 Introduction
13.2 Metal Strings with Oligopyridylamido and the Pyrazine‐Modulated Ligands
13.2.1 Nickel Metal‐String Complexes
13.2.2 Cobalt Metal‐String Complexes
13.2.3 Chromium Metal‐String Complexes
13.2.4 Ruthenium, Rhodium, and Iron Metal‐String Complexes
13.3 The New Generation of Metal‐String Complexes
13.4 Metal‐String Complexes as the Building Blocks in Coordination Polymers
13.5 Heteronuclear Metal‐String Complexes
13.5.1 Synthetic Strategies for HMSCs
13.5.2 MAMBMA HMSCs
13.5.3 MAMAMB HMSCs
13.5.4 MAMBMC HMSCs
13.5.5 Other HMSCs with More than Three Metal Atoms
13.6 Stereoisomers of Metal‐String Complexes
13.7 The Conductance of Metal‐String Complexes
13.8 Outlook
References
Epilogue
Index
EULA