Host-Guest Chemistry: Supramolecular Inclusion in Solution

Cover
Half Title
Also of Interest
Host–Guest Chemistry: Supramolecular Inclusion in Solution
Copyright
Dedication
Preface
Contents
List of Important Abbreviations and Symbols
List of Numbered Chemical Structures
1. Introduction
	1.1 Supramolecular chemistry
	1.2 Host–guest inclusion complexation in solution
	References
2. Historical aspects
	2.1 Early examples of host–guest inclusion compounds
	2.2 History of the development of major families of hosts
	2.3 Proliferation of host–guest inclusion research
	2.4 Current state of solution-phase host–guest inclusion chemistry
	References
3. Driving forces, thermodynamics, and kinetics of inclusion in aqueous solution
	3.1 Preparation, self-assembly, and mechanisms of inclusion complexation in aqueous solution
	3.2 Driving forces for inclusion in aqueous solution
		3.2.1 Intermolecular forces between host and guest
		3.2.2 Expulsion of water molecules from the host cavity
		3.2.3 The hydrophobic effect in aqueous solution
		3.2.4 Summary of driving forces for host inclusion in aqueous solution
	3.3 Thermodynamics of inclusion in solution
	3.4 Dynamics of inclusion in solution
	3.5 Host selectivity and modes of inclusion in solution
	References
4. Spectroscopic methods for studying host–guest inclusion in solution
	4.1 Quantum mechanics and molecular energy levels
	4.2 The nature of light and its interaction with molecules
	4.3 Infrared absorption spectroscopy
	4.4 UV–vis absorption spectroscopy
	4.5 Fluorescence spectroscopy
		4.5.1 Steady-state fluorescence spectroscopy
		4.5.2 Time-resolved fluorescence spectroscopy
	4.6 Phosphorescence spectroscopy
	4.7 NMR spectroscopy
	4.8 Other spectroscopic methods and conclusion
	References
5. Other experimental methods for studying host–guest inclusion in solution
	5.1 Electrochemical methods
	5.2 Calorimetric and other thermal methods
	5.3 Chromatographic methods
	5.4 Mass spectrometry methods
	5.5 Diffraction techniques
	5.6 Other miscellaneous methods
	References
6. Extraction of binding constants from experimental data
	6.1 Extraction of binding constants from experimental titration data for 1:1 host:guest complexes
		6.1.1 Benesi–Hildebrand analysis
			6.1.1.1 Modifications of the Benesi–Hildebrand method for applications to other types of experimental data
			6.1.1.2 Accuracy and limitations of the Benesi–Hildebrand method
		6.1.2 Nonlinear least-squares analysis of fluorescence titration data
	6.2 Experimental determination of host:guest complex stoichiometry
	6.3 Extraction of binding constants from experimental data for higher order host:guest complexes
	6.4 Error analysis and reproducibility of binding constants extracted from experimental titration data
	6.5 Other mathematical and/or experimental approaches
	References
7. Cyclodextrins as hosts
	7.1 Introduction to cyclodextrins
	7.2 Physicochemical properties of cyclodextrins
	7.3 Modified cyclodextrins
		7.3.1 Substitution at the primary hydroxyls
		7.3.2 Substitution at the secondary hydroxyls
		7.3.3 Specific examples of modified cyclodextrins used as molecular hosts
		7.3.4 Monosubstitution of tethered active moieties
	7.4 Host properties of native and modified CDs in aqueous solution
	7.5 Polymers containing CD host moieties
	7.6 Summary of CDs as molecular hosts
	References
8. Cucurbit[n]urils as hosts
	8.1 Introduction to cucurbit[n]urils
	8.2 Synthesis of cucurbit[n]urils
	8.3 Physicochemical properties of cucurbit[n]urils
	8.4 Cucurbit[n]urils as molecular hosts in aqueous solution
		8.4.1 Cucurbituril (cucurbit[6]uril) as host
		8.4.2 Cucurbit[7]uril as host
		8.4.3 Cucurbit[n]urils, n ≥ 8 as hosts
	8.5 A Comparison of the aqueous host binding properties of cucurbit[n]urils and CDs
	8.6 Cucurbit[n]uril derivatives and analogues as hosts in aqueous solution
	8.7 Cucurbit[n]urils as molecular beads in rotaxanes and building blocks for nanodevices
	8.8 Summary of cucurbit[n]urils as molecular hosts
	References
9. Other molecular hosts in aqueous solution
	9.1 Calix[n]arenes
	9.2 Cavitands
	9.3 Cryptands
	9.4 Cryptophanes
	9.5 Carcerands and hemicarcerands
	9.6 Dendrimers
	9.7 Pillar[n]arenes
	9.8 Bambus[n]urils
	9.9 Cyclophanes
	9.10 Other miscellaneous molecular hosts
	References
10. Host–guest inclusion in mixed aqueous and nonaqueous solution
	10.1 Introduction
	10.2 Host–guest inclusion in mixed aqueous-organic solution
	10.3 Host–guest inclusion in pure nonaqueous solution
		10.3.1 Cyclodextrin inclusion complexes in nonaqueous solution
		10.3.2 Inclusion complexes of other hosts in nonaqueous solution
	10.4 Conclusions
	References
11. Applications of host–guest inclusion in solution
	11.1 Analytical applications
	11.2 Molecular sensors and molecular recognition
	11.3 Control of guest reactivity
	11.4 Medicinal and pharmaceutical applications
	11.5 Water treatment and environmental remediation
	11.6 Industrial applications
	11.7 Other applications and summary
	References
12. Conclusions and summary
	References
Index