Table of Contents

Cover

Title Page

Dedication

Preface

Chapter 1: Introduction

1.1 History of Cyclodextrins
1.2 Cyclodextrin Properties
1.3 Inclusion Complex Formation Mechanism
1.4 Important Parameters in Inclusion Complex Formation
1.5 Inclusion Complex Formation Methods
1.6 Methods for Drying of Complexes
1.7 Release of the Complex
1.8 Application of Inclusion Compounds
1.9 Applications of Cyclodextrins
1.10 Characterization and Experimental Techniques
References

Chapter 2: Supramolecular Chemistry and Rotaxane

2.1 What Is Supramolecular Chemistry
2.2 Host–Guest Chemistry
2.3 Cyclodextrin-Containing Supramolecular Structures
2.4 Supramolecular Chemistry
2.5 Cyclodextrin-based Rotaxanes and Pseudorotaxanes
References

Chapter 3: Smart Polymers

3.1 Introduction
3.2 Supramolecular Self-Assembly
3.3 Synthesis of Block Copolymers
3.4 Self-Assembly of Amphiphilic Block Copolymers
3.5 Stimuli-Sensitive Supramolecular Structures
3.6 Polymers with Dual-Stimuli Responsiveness
3.7 Stimuli-Sensitive Polyrotaxane for Drug Delivery
3.8 Multi-Stimuli-Responsive Inclusion Complexes
References

Chapter 4: Basics of Corrosion

4.1 Introduction to Corrosion and Its Types
4.2 Corrosion Protection
4.3 An Introduction to Self-healing Coatings
4.4 Protective Coatings Containing Corrosion Inhibitors
4.5 An Introduction to Sol–Gel
4.6 Addition of Corrosion Inhibitors to Sol–Gel Coating Micro-/Nanoparticles
4.7 Self-healing Coating Containing Corrosion Inhibitor Capsules
4.8 Morphology of the Smart Corrosion Inhibitor Nanocontainers
4.9 Concluding Remarks
References

Chapter 5: Phytochemicals

5.1 Phenolic Acids
5.2 Flavanoids
5.3 Phytochemical Importance
5.4 Encapsulation
5.5 Encapsulation of Phenolic Compounds Via Cyclodextrin
5.6 Why Encapsulation by Cyclodextrin?
5.7 Concluding Remarks
References

Chapter 6: Cyclodextrins Application as Macroinitiator

6.1 Cyclodextrins Application as Macroinitiator in Polyrotaxane Synthesis Via ATRP
6.2 Inclusion Complexes of PDMS and γ-CD Without Utilizing Sonic Energy
6.3 Supramolecular Pentablock Copolymer Containing Via ATRP of Styrene and Vinyl Acetate Based on PDMS/CD Inclusion Complexes as Macroinitiator
6.4 Synthesis and Characterization of Poly(vinylacetate)-b-Polystyrene-b-(Polydimethyl siloxane/cyclodextrin)-b-Polystyrene-b-Poly(vinyl acetate) Pentablock Copolymers
6.5 Conclusion
References

Chapter 7: Cyclodextrin Applications

7.1 Cyclodextrin Industrial Applications
7.2 Drug Delivery Systems Based on Cyclodextrins
7.3 Cyclodextrin-based Targeting Systems
7.4 CDs in the Food Industry
7.5 Cyclodextrins in Skin Delivery and Cosmetic
7.6 Agricultural Applications
7.7 Self-healing Coating
References

Index

End User License Agreement

List of Illustrations

Chapter 1: Introduction

Figure 1.1 Schematic diagram of cyclodextrins.
Scheme 1.1 Schematic presentation of inclusion complex formation.
Figure 1.2 Inclusion complex between high-molecular-weight PEO and α-CD [90–93].
Figure 1.3 Schematic illustration of drug-conjugated polyrotaxane and the concept of drug release [93–95].

Chapter 2: Supramolecular Chemistry and Rotaxane

Figure 2.1 Schematic structure of Crown-6, Cryptand, and Spherand-6.
Scheme 2.1 Schematic presentation of electrostatic interaction.
Scheme 2.2 Schematic presentation of hydrogen bonding.
Scheme 2.3 Schematic presentation of van der Waals interactions.
Figure 2.2 Host or guest molecules which can be used for formation of supramolecular structures. (a) Crown ether, (b) calixarene, (c) cyclodextrin, and (d) spherand.
Figure 2.3 Self-assembled supramolecular structures.
Figure 2.1 Schematic presentation of (a) pseudorotaxane, (b) rotaxane, (c) poly pseudorotaxane, and (d) polyrotaxane.
Figure 2.5 Polyrotaxanes synthesis method based on nature and location of the bonding.
Figure 2.6 Orientation between CD and polymer chain based on hydrogen bonding.
Figure 2.7 Schematic presentation of (a) CD dimers and (b) molecular inclusion complex by a cyclodextrin vesicle.
Figure 2.8 Synthesis of catenane by linking both end of a thiol threaded into α-CD in the presence of copper(II) ions and oxidation in the presence of air.
Figure 2.9 Schematic synthesis of rotaxane via two methods, (a) synthesis of a pseudorotaxane and then reaction with bulky blocking group and (b) formation of an inclusion complex containing a guest molecule with one blocking agent at the end and reaction with another blocking agent.
Figure 2.10 Self-assembly of a rotaxane using threading procedure.
Figure 2.11 CD-based rotaxane prepared using a slippage method.
Figure 2.12 Schematic representation of side- and main-chain polyrotaxanes.
Figure 2.13 Main chain polyrotaxane by using (a) small blocking group and (b) a larger blocking group.
Figure 2.14 Side-chain polyrotaxane from methylated β-CD (X = O−COOEt).
Figure 2.15 Tubular polyrotaxane based on α-CD from stacked polyrotaxane rings.
Figure 2.16 Schematic presentation of Tandem side-chain polyrotaxane.
Figure 2.17 Synthesis of cyclodextrin molecular tubes.

Chapter 3: Smart Polymers

Figure 3.1 Classification of polymerization methods.
Scheme 3.1 Nitroxide-mediated polymerization mechanism.
Scheme 3.2 Atom transfer radical polymerization mechanism.
Scheme 3.3 Reversible addition–fragmentation chain transfer mechanism.
Figure 3.2 Classification of polymers and copolymers based on repeating unit.
Figure 3.3 Schematic presentation of polymeric micelles.
Figure 3.4 Self-assembled structure in diluted regime.
Figure 3.5 (a) Spherical micelles and (b) spherical vesicles.
Figure 3.6 Classification of dendrimer supramolecular structures.
Figure 3.7 Equilibrium state between compacted and expanded state of polymer chains.
Figure 3.8 Multistimuli nanogel tend which released drug under pH or temperature differences.
Figure 3.9 (a) Poly(N-isopropylacrylamide) (PNIPAAm), (b) poly(N,N-diethylaminoethyl methacrylate) (PDEAEMA), (c) poly(N,N′-diethylacrylamide) (PDEAAm), (d) poly(2-carboxyisopropylacrylamide) (PCIPAAm), and (e) poly[2-(methacryloyloxy)ethyl]-dimethyl(3-sulfopropyl) ammonium hydroxide (PMEDSAH).
Figure 3.10 (a) Poly(N-isopropyl acrylamide)PNIPAM, (b) poly(N-vinylcaprolactam) PNVCL, (c) poly(methyl vinyl ether) PMVE, (d) poly(N,N-dimethylacryl amide) PDEAM,(e) poly(N-methylmethacrylamide) PNEMAM, and (f) poly(2-ethoxyethyl vinyl ether) PEOVE.
Figure 3.11 Phase transfer of thermoresponsive polymers.
Figure 3.12 (a) Spiropyrans, (b) flugides, (c) diarylethenes, and (d) azobenzene.
Figure 3.13 Schematic representation of (a) photochromic containing block copolymers and (b) photodegradable block copolymers.
Figure 3.14 Schematic representation of electroresponsive polymers.
Figure 3.15 Schematic design for pH-responsive CD–polypseudorotaxane and polyrotaxane hydrogels.
Figure 3.16 Vesicle self-assembly PEO-b-PAA induced by the complexation with CD.
Figure 3.17 Photoresponsive inclusion complexes containing (a) azobenzene and (b) stilbene.
Figure 3.18 Drug released from pH-sensitive hydrogel containing CD and polymer chain.
Figure 3.19 Possible shuttling process in stimuli-responsive rotaxane.
Figure 3.20 Light-driven molecular shuttle based on CD.
Figure 3.21 Photoresponsive rotaxane based on strong hydrogen bonding between OH groups of CD and two carbonyl groups in phthalic acid unit.
Figure 3.22 Stilbene-based photoresponsive polyrotaxane.
Figure 3.23 Photoresponsive α-CD/NPSI inclusion complex [187].
Figure 3.24 Azobenzene-based rotaxane conformations.
Figure 3.25 Redox-responsive gel-to-sol transition based on CD and ferrocenecarboxylic acid.
Figure 3.26 Temperature- and UV-responsive rotaxane based on AZO-PNIPAM and Au nanoparticles.
Figure 3.27 UV- and light irradiation of PDMAA-co-PAPA/CD rotaxanes.

Chapter 4: Basics of Corrosion

Figure 4.1 Uniform corrosion attack on structural steel.
Figure 4.2 Galvanic corrosion occurred on the aluminum plate along the joint with the mild steel within 2 years due to the huge acceleration factor in galvanic corrosion.
Figure 4.3 ASTM-G46 has a standard visual chart for rating of pitting corrosion.
Figure 4.4 Crevice corrosion of stainless steel tube due to the presence of crevice (gap) between the tube and tube sheet.
Figure 4.5 Intergranular corrosion or intergranular stress corrosion cracking.
Figure 4.6 Graphitic corrosion of a gray cast iron valve.
Figure 4.7 Intrinsic self-healing materials (a) reversible bonding schemes make use of the reversible nature of certain chemical reactions; (b) chain entanglement approaches use the mobility at crack faces to entangle chains that span the crack surfaces; and (c) noncovalent self-healing systems rely on reversible hydrogen bonding or ionic clustering, which manifests as reversible cross-links in polymers.
Figure 4.8 Capsule-based healing process.
Figure 4.9 Chemical reaction of urea with formaldehyde prepolymer formation.
Figure 4.10 Chemical formula of the cross-linked polyurea–formaldehyde capsule shell.
Figure 4.11 Mechanism of self-healing coating.
Figure 4.12 Schematic diagram for sol–gel process.
Figure 4.13 (a) Molecular structure of cyclodextrins and (b) formation of inclusion complex with guest molecule.
Figure 4.14 Schematic presentation of CD/mercaptobenzimidazole (MBI) and CD/mercaptobenzothiazole (MBT) inclusion complex formation.
Figure 4.15 ¹H NMR of (a) α-CD, (b) 2-MBT, (c) α-CD/MBT at room temperature, (d) α-CD/MBT under sonic energy, (e) α-CD/MBI at room temperature, (f) α-CD/MBI under sonic energy, and (g) MBI.
Figure 4.17 ¹H NMR of (a) γ-CD, (b) MBT, (c) γ-CD/MBT at room temperature, (d) γ-CD/MBT under sonic energy, (e) γ-CD/MBI at room temperature, (f) γ-CD/MBI under sonic energy, and (g) MBI.
Figure 4.18 XRD spectra of (a) α-CD, (b) α-CD/MBT at room temperature, (c) α-CD/MBT under sonic energy, (d) α-CD/MBI at room temperature, and (e) α-CD/MBI under sonic energy.
Figure 4.20 XRD spectra of (a) γ-CD, (b) γ-CD/MBT under sonic energy, (c) γ-CD/MBT at room temperature, (d) γ-CD/MBI under sonic energy, and (e) γ-CD/MBI at room temperature, and (e) γ-CD.
Figure 4.21 SEM images of coating containing inclusion complex of α-CD or β-CD and inhibitor nanocontainers at various conditions.
Figure 4.22 SEM images of coating containing inclusion complex of γ-CD and inhibitor nanacontainers at room temperature.
Figure 4.23 TEM images of coating containing CD/MBT nanocontainers at room temperature (a) α-CD, (b) β-CD, and (c) γ-CD.
Figure 4.24 Potentiodynamic scans for coating containing encapsulated inhibitor at room temperature dilute 5% NaCl solution.
Figure 4.25 The electrochemical impedance spectra for scribed coatings with different inhibitor nanocontainers in 5% NaCl solution.
Figure 4.26 Results of 1000-h salt spray tests for aluminum alloy substrates coated with coating containing corrosion inhibitor nanocontainers.
Figure 4.27 Calibration curve for nanocontainers at room temperature.
Figure 4.28 Release of coating containing nanocontainers of corrosion inhibitor and (a) α-CD and (b) β-CD at various conditions.

Chapter 5: Phytochemicals

Figure 5.1 Classification of phytochemicals.
Figure 5.2 Chemical structures of some phenolic compounds.
Figure 5.3 Some polyphenol structures.
Figure 5.1 Flavanoid structure.
Figure 2.5 Chemical structures of flavonoids.
Figure 2.6 Schematic images of (a) epigallocatechin-3-gallate, (b) quercetin, and (c) curcumin.
Figure 2.7 Various types of core–shell structures.
Figure 2.8 Most common morphologies for encapsulation of polyphenols (a) monomer capsule and (b) aggregate.
Figure 2.9 Encapsulation by emulsion/extraction and emulsion/evaporation method.
Figure 5.10 Schematic image of encapsulation by coacervation method.
Figure 5.11 Cross section of polymeric micelles.
Figure 5.12 Phospholipid bilayers for protection of drug, gen, and polyphenol compounds.
Figure 5.13 In situ polymerization is a chemical microencapsulation process.
Figure 5.14 Principle of the microcapsulation by interfacial polymerization: (a) the oligomer is soluble in the droplet and (b) the oligomer is insoluble in the droplet.
Figure 5.15 Inclusion complex formation between CD and the guest molecule.

Chapter 6: Cyclodextrins Application as Macroinitiator

Figure 6.1 Continuous variation plot for complex formation between γ-CD and PDMS under sonic energy.
Figure 6.2 FTIR spectra of γ-CD/PDMS complexes at various conditions: (a) PDMS–γ-CD, 7 days at room temperature; (b) PDMS–γ-CD under sonic energy at room temperature; (c) PDMS–Br, 7 days at room temperature; and (d) PDMS–γ-CD without mixing or light, 7 days at room temperature.
Figure 6.3 Powder X-ray diffraction patterns (solid state) of γ-CD/PDMS complexes at various conditions: (a) PDMS–γ-CD, 7 days at room temperature; (b) PDMS–Br, 7 days at room temperature; (c) PDMS–γ-CD under sonic energy at room temperature; (d) PDMS–γ-CD without mixing at room temperature; and (e) PDMS–γ-CD, 7 days at room temperature without mixing or light.
Figure 6.4 ¹H NMR spectra of the complex between γ-CD/PDMS complexes at various conditions: (a) PDMS–γ-CD, 7 days at room temperature; (b) PDMS–γ-CD under sonic energy at room temperature; (c) PDMS–γ-CD, 7 days at room temperature without mixing or light; and (d) PDMS–Br, 7 days at room temperature.
Figure 6.5 DSC spectra of (a) γ-CD and the complex between PDMS/γ-CD, (b) 7 days at room temperature without mixing or light, (c) under sonic energy at room temperature, and (d) 7 days at room temperature.
Scheme 6.1 ATRP route of PVAc and PSt initiated with (Br–PDMS–Br/CD) macroinitiators.
Figure 6.6 ¹H NMR spectra of HO–PDMS–OH (a) and Br–PDMS–Br macroinitiator (b) in the CDCl₃ solvent.
Figure 6.7 Powder X-ray diffraction patterns (solid state) of γ-CD/Br–PDMS–Br inclusion complexes at various conditions: (a) Br–PDMS–Br/γ-CD under sonic energy at room temperature; (b) Br–PDMS–Br/γ-CD, 7 days at room temperature; and (c) Br–PDMS–Br/γ-CD without mixing or light, 7 days at room temperature.
Figure 6.8 (a) Time dependence of ln[M]₀/[M] (M: monomer) and (b) dependence of the pentablock copolymer M_n on the conversion for the ATRP of St and PVAc with Br–PDMS–Br/γ-CD macroinitiator, which is synthesized from various conditions at 60 °C.
Figure 6.9 ¹H NMR of PSt-b-PVAc-b-PDMS/γ-CD-b-PVAc-b-PSt initiated with inclusion complex of γ-CD/Br–PDMS–Br synthesized from (a) 7 days at room temperature, (b) under sonic energy (15 min), and (c) 7 days at room temperature without light and mixing.
Figure 6.10 DSC thermograms for the (a) PSt-b-PVAc-b-(PDMS/γ-CD)-b-PVAc-b-PSt initiated with inclusion complex of γ-CDs/Br–PDMS–Br synthesized at (a) 7 days at room temperature, (b) under sonic energy (15 min), and (c) 7 days at room temperature without light and mixing.
Figure 6.11 ¹H NMR of thermoreversible PSt-b-PVAc-b-PDMS/γ-CD-b-PVAc-b-PSt block copolymers initiated with inclusion complex of γ-CD/PDMS (synthesized 7 days at room temperature) at (a) 22 °C, (b) 55 °C, and (c) 22 °C.
Figure 6.12 XRD of thermoreversible PSt-b-PVAc-b-PDMS/γ-CD-b-PVAc-b-PSt block copolymers initiated with inclusion complex of γ-CD/Br–PDMS–Br (synthesized 7 days at room temperature) at (a) 22 °C, (b) 55 °C, and (c) 22 °C.
Scheme 6.2 Reaction scheme for synthesis of bis(2-bromoisobutyrate)-terminated PDMS macroinitiator from bis(hydroxyalkyl)-terminated PDMS.
Figure 6.13 ¹H NMR of PVAc-b-PSt-b-[γ-CD/PDMS]-b-PSt-b-PVAc initiated with inclusion complex of γ-CD/PDMS synthesized from (a) 7 days at room temperature, (b) under sonic energy, and (c) 7 days at room temperature without light and mixing [VAc:St:(PDMS/CDs) = 1:2:0.5].
Figure 6.14 First-order kinetic plot for the ATRP of St and PVAc initiated by Br–PDMS/CDs at 60 °C for 6 h.
Figure 6.15 ¹H NMR thermograms for the PVAc-b-PSt-b-[CD/PDMS]-b-PSt-b-PVAc: (a) γ-CD/PDMS, (b) β-CD/PDMS, and (c) α-CD/PDMS initiated with inclusion complex of CD/PDMS at 60 °C for 6 h [VAc:St:(PDMS/CDs) = 1:2:0.5].
Figure 6.16 DSC thermograms for the (a) PSt-b-PVAc-b-PDMS-b-PVAc-b-PSt, (b) PSt-b-PVAc-b-(PDMS/α-CD)-b-PVAc-b-PSt, (c) PSt-b-PVAc-b-(PDMS/β-CD)-b-PVAc-b-PSt, and (d) PSt-b-PVAc-b-(PDMS/α-CD)-b-PVAc-b-PSt initiated with inclusion complex of CDs/PDMS at 60 °C for 6 h [VAc:St:(PDMS/CDs) = 1:2:0.5].

List of Tables

Chapter 1: Introduction

Table 1.1 Cyclodextrin properties

Chapter 5: Phytochemicals

Table 5.1 Encapsulation methods applied to polyphenols

Chapter 6: Cyclodextrins Application as Macroinitiator

Table 6.1 Conversion of γ-CD/PDMS for various conditions
Table 6.2 Assignments of FTIR of PDMS/γ-CD
Table 6.3 GPC and ¹H NMR results of PSt-b-PVAc-b-[γ-CD/PDMS]-b-PVAc-b-PSt initiated with γ-CD/Br–PDMS–Br synthesized from various conditions
Table 6.4 Summary of the results obtained from GPC and ¹H NMR analyses of PSt-b-PVAc-b-[γ-CD/PDMS]-b-PVAc-b-PSt initiated with γ-CD/PDMS synthesized from various conditions [VAc:St:(PDMS/CDs) = 1:2:0.5]
Table 6.5 Summary of the results obtained from GPC and ¹H NMR analyses of PSt-b-PVAc-b-(PDMS/CDs)-b-PVAc-b-PSt initiated with PVAc macroinitiator from bulk telomerization in the presence of Co(acac)₂ at 60 °C for 6 h [VAc:St:(PDMS/CDs) = 1:2:0.5]

Cyclodextrins

Properties and Industrial Applications

Sahar Amiri

Department of Polymer Engineering
Islamic Azad University, Tehran, Iran

Sanam Amiri

Department of Textile Engineering
Amirkabir University of Technology
Tehran, Iran

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Cover images: (Background) © Mandy Disher Photography/Gettyimages; (Small molecule) © Molekuul/Gettyimages; (Big molecule) © theasis/Gettyimages

The basis of a life as a scientist is a warm and supportive home life. It would have been impossible without my mother and father who supported me throughout my life.

Preface

Cyclodextrins (CDs) are a family of cyclic oligosaccharides consisting of (α-1,4)-linked α-d-glucopyranose units. CDs are obtained from the enzymatic digestion of the most essential polysaccharides, starch, and cellulose. The specific donate shape (truncated cone) of CDs is due to the chair conformation of the glucopyranose units and leads to a hydrophobic cavity and a hydrophilic surface. CDs can form host–guest interaction with a wide range of hydrophobic and hydrophile segments and encapsulate molecules in their hydrophobic cavity. Encapsulation in a CD cavity may alter or improve the physical, chemical, biological characteristics, and stability of the guest molecule. The formation of inclusion complexes between CDs as host and guest molecules is based on noncovalent interaction such as hydrogen bonding or van der Waals interactions and leads to the formation of supramolecular structures. These structures can be used as macroinitiators to initiate various types of reactions. CDs are widely used in many industrial products such as pharmacy, food and flavors, chemistry, chromatography, catalysis, biotechnology, agriculture, cosmetics, hygiene, medicine, textiles, drug delivery, packing, separation processes, environment protection, fermentation, and catalysis.

One of the most attractive applications of CDs is their role as molecular encapsulants in food and drug industries. Encapsulation of phytochemicals and flavors in food industry allows the quality and quantity of the flavor to be preserved to a greater extent for longer periods compared to other encapsulants; it provides longevity to the food item, and also masks its unpleasant odor. CDs are potential candidates for increasing the solubility of hydrophobic drugs, delivering the required amount of drug to the targeted site for the necessary period of time, both efficiently and precisely, and limiting undesirable properties of drug molecules. These characteristics have lowered drug production costs.

Inclusion complex formation between CDs and guest molecules is based on reversible and noncovalent bonding strategies and can be used as self-healing agents for various purposes. CDs can encapsulate corrosion inhibitors, become active in corrosive electrolytes, slowly diffuse out of the host material to ensure both continuous and controlled delivery of the inhibitors to corrosion sites and long-term corrosion protection.

Each year, many patents, research articles, books, and scientific abstracts are published about CDs and their applications in various fields, but many aspects of CDs and their derivatives are still unknown and attractive. That is why we focused on CDs and their applications in various fields.

This book reflects cyclodextrins structure, their properties, formation of inclusion complex with various compounds, and their applications. The purpose of this book is to cover both basic and applied science in chemistry, biology, and physics of CDs. We hope that this book will arouse the interest of scientists and engineers who wish to diversify their research fields.

Tehran, June 2017

Sahar Amiri
Sanam Amiri