The book is designed to highlight the utility of supramolecular systems in diverse areas such as sensing of ionic and molecular analytes, aggregation, artificial molecular machines, biology, and medicine. The synthetic chemistry of a diverse set of supramolecules encompassing various supramolecular interactions involved in driving macrocyclic architectures is discussed. Attempts have been made to cover unique features of macrocycles viz. control over shape, size, and valency along with supramolecular interactions, which direct complex supramolecular systems. The book also provides a discussion on the similarity between macrocyclic host-guest systems and biomolecules, which lay the foundation of building modern artificial molecular motors and switches like protein machines for application in diverse areas. The authors hope that the book will appeal to a wider audience of students and researchers in academics and/or industries.
Author(s): Satish Kumar, Priya Ranjan Sahoo, Violet Rajeshwari Macwan, Jaspreet Kaur, Mukesh, Rachana Sahney
Publisher: CRC Press/Science Publishers
Year: 2022
Language: English
Pages: 474
City: Boca Raton
Cover
Title Page
Copyright Page
Preface
Table of Contents
Chapter 1 Macrocyclic Receptors Synthesis, History, Binding Mechanism: An Update on Current Status
Introduction
Macrocyclic Receptors and Types
Crown Ethers
Synthesis of Crown Ether
Binding Mode of Crown Ether
Cryptands
Synthesis of Cryptands
Cyclodextrins
Synthesis of Cyclodextrins
Calixarenes
Synthesis of Calixarenes
Resorcinarenes
Synthesis of Resorcinarenes
Multifarenes
Calixpyrroles
Synthesis of Calixpyrroles
Synthesis of N-confused Calix[4]pyrrole
Helic[6]arenes
Synthesis of Helic[6]arenes
Cyanostars
Synthesis of Cyanostars
Oxatub[4]arene
Pillararenes
Synthesis of Pillararenes
Homo-cyclooligomeri
Co-cyclooligomerization
Prismarenes
Synthesis of Prismarenes
Cucurbiturils
Bambus[n]urils
Cyclotriveratrylenes
Synthesis of Cyclotriveratrylene
Cryptophanes
Synthesis of Cryptophanes
Rotaxanes and Catenanes
Synthesis of Rotaxanes and Catenanes
Functionalized Tetrathiafulvalenes
Synthesis of Tetrathiafulvalenes
Conclusions
References
Chapter 2 Macrocyclic Receptors for Environmentally Sensitive Metal Ions
Introduction
Macrocyclic Receptors for Alkali Metal Ions
Macrocyclic Receptors for Li + Ions
Macrocyclic Receptors for Na+ Ion
Macrocyclic Receptors for K+ Ions
Macrocyclic Receptors for Cs+ Ions
Macrocyclic Receptors for Alkaline Earth Metal Ions
Macrocyclic Receptors for Mg2+ Ions
Macrocyclic Receptors for Ca2+ Ions
Macrocyclic Receptors for Sr2+ Ions
Macrocyclic Receptors for Ba2+ Ions
Macrocyclic Receptors for Transition and Heavy Metal Ions
Macrocyclic Receptors for Fe3+ Ions
Macrocyclic Receptors for Cu2+ Ions
Macrocyclic Receptors for Zn2+ Ions
Macrocyclic Receptors for Cd2+ Ions
Macrocyclic Receptors for Hg2+ Ions
Macrocyclic Receptors for Pb2+ Ions
Macrocyclic Receptors for Tl+ Ions
Macrocyclic Receptors for Lanthanide and Actinide Ions
Conclusion
References
Chapter 3 Macrocyclic Receptors for Precious Metal Ions
Introduction
Macrocyclic Receptors for Ag+ Ions
Macrocyclic Receptors for Au3+ Ions
Macrocyclic Receptors for Pd2+ Ions
Conclusion
References
Chapter 4 Macrocyclic Anion Receptors
Introduction
Parameters that Affect Anion Complexation
Receptors for Anions
Measurement Techniques
Bile Acid-based Macrocycles as Anion Receptors
Calix[4]pyrroles Based Macrocycles as Anion Receptors
Redox-active Receptors as Anion Receptors
Porphyrin Cages Based Macrocycles as Anion Receptors
Conclusions
References
Chapter 5 Macrocyclic Receptors for Sensing the Environmentally Important Gaseous Molecules
Introduction
Definition
Challenges
Role of Macrocyclic Compounds in Gas Sensing
Overview of a Few Different Types of Sensing Techniques
Quartz Micro Balance (QMB)
Langmuir–Blodgett Method (LB)
Surface Acoustic Wave Oscillator (SAW)
Thin-film Bulk Acoustic Resonator (FBAR or TFBAR)
Surface Plasmon Resonance
Solid-Phase Micro Extraction (SPME)
Evanescent Field Wave Sensor
Sensing of Environmentally Important Gases
Volatile Organic Compounds
BTEX
Cyclodextrins
Calixarenes
Other Cavitands
Nitrogen-containing Basic Gases and Volatile Compounds
Cyclodextrin
Calixarenes
Acidic Vapours
Hydrochloric Acid
Nitrogen Oxides NOx
Calix[4]arenes
Cucurbituril
Carbon Dioxide (CO2)
Organic Carboxylic Acid Vapors
Neutral Gaseous Molecules
Conclusion
References
Chapter 6 pH-Responsive Pseudorotaxanes and Rotaxanes
Introduction
Pseudorotaxane
Cucurbiturils CB[n] based pH Responsive Pseudorotaxanes
Pillar[5]arene based pH Responsive Pseudorotaxanes
Cyclodextrin based pH Responsive Pseudorotaxanes
Rotaxanes
pH-responsive [2]rotaxane
pH-responsive [3]rotaxane
pH-responsive [4]rotaxane
pH-responsive [c2]daisy Chain Rotaxanes
pH-responsive Rotaxane based Polymers/Gel/Rotaxane Immobilized into the Framework
Interconversion of Pseudorotaxane and Rotaxanes on the Addition of Acid/Base
Conclusion
References
Chapter 7 Macrocyclic Receptors for Biomolecules and Biochemical Sensing
Introduction
Introduction to Structure and Properties: Nucleotides, Nucleosides and Nucleic Acid
Nucleosides and Nucleotides
Oligonucleotides and Nucleic Acids
Macrocyclic Receptors for Nucleotides, Nucleosides and Nucleic Acid
Introduction to Structure and Properties of Sugars/Carbohydrates
Macrocyclic Receptors for Carbohydrates
Introduction to Structure and Properties of Amino Acid, Peptide and Proteins
Macrocyclic Receptors for Amino Acids, Peptides, and Proteins
Introduction to Structure and Function of Biological Lipids
Macrocyclic Receptors for Molecular Recognition of Lipids
Conclusion and Outlook
References
Chapter 8 Macrocyclic Receptors for Biologically Relevant Metal Ions
Introduction
Metallocycles as an Anticancer Drug
Metallo-macrocycle as Magnetic Resonance Imaging (MRI) Contrast Agent
Metallomacrocycles as Synthetic Enzyme
Conclusion and Outlook
References
Chapter 9 Molecular Machines based on Macrocyclic Receptors: Switches and Motors
Introduction
Terminology
Macrocycles Hosts: Implements of the Trade
Cyclodextrins (CDs)
Coronands and Cryptands
Cyclic Arenes and Analogous Deep Cavitands
Cucurbituril
Blue Box and its Derivatives (Exboxes)
Stimuli-Responsive Molecular Switches
Mechanically Interlocked Molecular Structures
Rotaxane
Pseudorotaxane
Molecular Switches
Conformational Control using Host-guest Interaction
Using Capping on the Macrocyclic Hosts
pH-Driven Threading and Dethreading (Pseudorotaxane)
Redox Driven Threading and Dethreading
Light-driven Switching
Molecular Tweezers
Orthogonal Control over Switching
Intramolecular Translocation of Ions with Stimuli
Excited-State Intramolecular Proton Transfer (ESIPT)
Self-complexing Pseudorotaxanes
Gated regulation of the Binding Site of the Host in Self-inclusive Pseudorotaxanes
Self-inclusive Pseudorotaxnes with an Externally Switchable Configuration of the Pendant for Gated Regulation of Binding Site
Allosteric Regulation of Linker Controlled Gated Regulation of Binding Site
Shuttling in Rotaxanes
Degenerate Molecular Shuttles with two Stations
Stimuli-responsive Molecular Shuttles
Stimuli-Responsive Molecular Shuttles with two or More Stations
Molecular Shuttles Driven by pH Change
Redox Driven Molecular Shuttling
Photodriven Molecular Shuttles
Ion-Induced Changes driving Molecular Shuttles
Shuttling Driven by Reversible Covalent Modification
Molecular Motors
Directional Motion and Work under Brownian Motion
Molecular Ratchet based on Rotaxanes/Pseudorotaxanes
Conclusion
References
Chapter 10 Role of Macrocyclic Receptors in Surface Self-assembly
Introduction
Macrocyclic Amphiphilic Structures
Macrocyclic Amphiphilic Structures based on Calix[n]arenes and Resorcinarenes
Macrocyclic Amphiphiles based on Calix[n]crowns
Macrocyclic Amphiphiles based on Resorcinarenes
Macrocyclic Amphiphiles based on Cyclodextrins
Self-assemblies of Macrocyclic Receptors based on Cucurbit[n]urils (CB[n])
Self-assembly of Macrocyclic Receptors based on Pillararenes
Aggregation Induced Emission (AIE) for Chemo/Bio-Sensing
Pillar[n]arene-based Supra-amphiphiles for Biological Imaging
Control of pH over Self-assembly
Calix[n]arene based pH Responsive Assemblies
Pillar[n]arenes based pH Responsive Assemblies
Cyclodextrin based pH Responsive Assemblies
Redox Responsive Assembly of Macrocycles
Sulfonatocalix[n]arenes-based Supramolecular Amphiphiles with Photo-responsiveness
Conclusions
References
Chapter 11 Stimuli-responsive Macrocyclic Receptors
Introduction
Light Responsive Receptors
Classification of Photoactive Receptors
Advantages of Photoactive Receptors
Light Responsive Metal Ions Macrocyclic Receptors
Lead Selective Receptors
Light Responsive Receptors for Lanthanides and Actinides
Light Controlled Complex with Multiple Ions
The pH-responsive Receptors
Thermo-responsive Receptors
Redox Driven Receptors
Disulfide-Bond Dependent Redox Responsive Macrocyclic Receptor
Ferrocene based Macrocyclic Receptor
Redox Responsive Systems based on Electroactive Guests
Conclusions
References
Index
About the Authors
