NMR-Diffusion Ordered Spectroscopy (NMR-DOSY)

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Table of contents

ACKNOWLEDGEMENTS
ABBREVIATIONS
ABSTRACT
RÉSUMÉ
CHAPTER 1 FROM SUPRAMOLECULAR CHEMISTRY TO SUPRAMOLECULAR POLYMERS
1. Supramolecular Chemistry
1.1. Introduction
1.2. The origins of supramolecular chemistry
1.3. From molecular to supramolecular chemistry
1.4. Nature of supramolecular interactions
1.4.1. Ionic-dipolar interactions
1.4.2. Van der Waals interactions
1.4.3. π-Interactions
1.4.4. Hydrogen bonding
1.4.5. Hydrophobic effects
2. Supramolecular Polymer
2.1. Definition
2.2. Mechanisms of association of supramolecular polymers
2.3. Properties of supramolecular polymers
2.3.1. Optoelectronic properties
2.3.2. Mechanical properties
2.3.3. Biological properties
2.4. Driving forces for supramolecular polymers
2.4.1. Multiple hydrogen bonds
2.4.2. Metal coordination bonds
2.4.3. Host-guest interaction
2.5. Characterizations of supramolecular polymers
2.5.1. NMR spectroscopy
2.5.1.1. 1H-NMR
2.5.1.2.NMR-Rotating-frame nuclear Overhauser Effect SpectroscopY
2.5.1.3. NMR-Diffusion Ordered SpectroscopY (NMR-DOSY)
2.5.2. Isothermal Calorimetric Titration (ITC)
2.5.3. Dynamic Light Scattering (DLS)
2.5.4. Viscometry
2.5.5. Small-Angle Neutron Scattering (SANS)
3. Cyclodextrins Based Supramolecular Polymers
3.1. Cyclodextrin (CD)
3.1.1. Structure and properties of cyclodextrin
3.1.2. Properties of cyclodextrin cavity
3.1.2.1. Inclusion complex of cyclodextrins
3.1.2.2. Guest of inclusion complex of cyclodextrins
3.1.3. Reactivity of cyclodextrins
3.2. Supramolecular polymers based on cyclodextrin in solution
3.2.1. Supramolecular polymers of AnBm type
3.2.2. Supramolecular polymers of AB type
4. Conclusion
CHAPTER 2 DESIGN STRATEGY AND SYNTHESIS OF SUPRAMOLECULAR POLYMERS BASED ON BETA-CYCLODEXTRIN-ADAMANTANE IN AQUEOUS SOLUTION
1. Selective Functionalization of Cyclodextrins Debenzylation
1.1. Synthesis of cyclodextrin diol with diisobutylaluminum hydride
1.2. Mechanism of DIBAL-H mediated debenzylation
1.3. Selectivity rationalization for α- and β-cyclodextrins debenzylation
2. Our Previous Work: Supramolecular Polymerization Based on β-Cyclodextrin- Adamantane in Aqueous Solution
2.1. Initial considerations and preliminary experiences
2.2. Further experiences with new strategies
3. System Design
4. Synthesis of Functionalized CD/Adamantane Monomers
4.1. General retrosynthesis
4.2. Synthesis of the common precursor: bi-azide cyclodextrin
4.3. Synthesis of bridged neutral cyclodextrin/adamantane monomer
4.4. Synthesis of bridged cationic cyclodextrin/adamantane monomer
4.5. Synthesis of difunctionalized bridged β-cyclodextrin-adamantane monomer: functionalized 1-deoxynojirimycin derivative
4.6. Conclusion of synthesized cyclodextrin/adamantane monomers
5. Conclusion
CHAPTER 3 STUDY OF SUPRAMOLECULAR ASSEMBLIES BASED ON BETA-CYCLODEXTRIN- ADAMANTANE IN AQUEOUS SOLUTION
1. Characterization of the Supramolecular Assembly
1.1. Characterization of supramolecular assembly by 1H-NMR
1.2. Characterization of supramolecular assembly by NMR-ROESY
1.3. Characterization of supramolecular assembly by NMR-DOSY
1.4. Characterization of supramolecular assembly by ITC
1.5. Characterization of supramolecular assembly by viscosity
1.6. Characterization of supramolecular assembly by DLS
2. Study Influence Factors on Polymerization of Supramolecular Polymer
3. Conclusion
CHAPTER 4 GENERAL CONCLUSION AND PERSPECTIVE
1. General Conclusion
2. Perspectives
APPENDIX
EXPERIMENTAL PART
1. General Procedures
2. Nomenclature for Protons
3. Synthesis
BIBLIOGRAPHY