1. New Insight into the Physical, Catalytic and Recognition Properties of Cucurbituril Macrocycles
- Author
-
Lu, Xiaoyong
- Subjects
- Chemistry, Cucurbituril, Recognition, Catalysis, Self-sorting, Molecular Switch, Gas Encapsulation, Conformational Freezing, Kinetics, Thermodynamics, Silver Nanoparticles.
- Abstract
Specific recognition and catalysis are key features of enzymes. Using artificial molecules to mimic the function of enzymes, allows chemists to understand their behavior, and to design an enzyme-like devices. Herein, the novel physical, catalytic and recognition properties of a series of pumpkin-shaped macrocycles named cucurbit[n]urils (CB[n]) were evaluated by spectroscopic methods including 1D and 2D NMR, HRMS, UV-Visible and TEM. We assessed the self-sorting systems incorporating multiple-CB[n] units and a spermine derivative; we studied the stabilization of gaseous fluorotrimethylsilane and designed a fluoride-controlled molecular switch; we also examined the regio- and diastereoselective encapsulation of a series of di- and tribenzylammonium cations and showed how CB[n]s could freeze selected conformations. Finally, CB[n]s were found to catalyze intramolecular Diels-Alder reactions by up to 2500-fold, and a silver-promoted desilylation by up to 6.6-fold. These macrocycles could also stabilize silver nanoparticles and control their size distribution.
- Published
- 2013