T ABLE OF C ONTENT
Abstract...i
Acknowledgments...vii
Table of Content...xi
List of Abbreviations...xv
List of Figures...xvii
List of Tables...xxiii
1. Chapter 1. General Introduction...1
1.1. Supramolecular chemistry...3
1.2. Calix[6]arenes...5
1.3. Funnel complexes...10
1.3.1. Calix[6]N
3...11
1.3.2. Calix[6]aza-cryptands...13
1.4. Calix[6]ureas-based receptors...16
1.4.1. Complexation of ion-pairs: the strategy...16
1.4.2 Calix[6]ureas for contact ion-pair recognition...17
1.5. Aim of the thesis...22
2. Chapter 2. Study of a fluorescent calix[6]arene for the recognition of anions, contact ion-pairs and phospholipids...25
2.1. Complexation of anions and contact ion-pairs...27
2.1.1. Context of the research...27
2.1.2. Summary of published results...28
2.2. Complexation of phospholipids...65
2.2.1. Context of the research...65
2.2.2. Summary of published results:...67
2.3. Conclusions...99
3. Chapter 3. Incorporation and study of cavitands in micelles ...101
3.1. Introduction...103
3.2. Examples of micellar incorporation of molecular receptors...106
3.3. Aim of the work...108
3.4. Summary of published results...110
3.5. Micellar incorporation of other systems...129
3.5.1. Incorporation of a homoxacalix[3]arene into DPC micelles...129
3.5.2. Incorporation of a resorcin[4]arene derivative into DPC micelles...135
3.6. Conclusions...143
4. Chapter 4. Funnel complexes: study of exchange dynamics...145
4.1. Introduction...147
4.2. 1D-EXSY NMR...152
4.3. Results and discussion...156
4.3.1. Effect of water on guest exchange with system 1.Zn
2+...156
4.3.2. Steric hindrance...163
4.3.3. Penta-coordinated zinc complex...167
4.3.4. Discussion and interpretation...172
4.4. Conclusions...175
5. Chapter 5. Conclusions...177
6. Chapter 6. Materials and methods...183
Chemicals...185
General procedures for
1H spectra...185
Micellar solutions preparation...186
1
H NMR characterization of various complexes with 15...186
General procedure...187
1