High-definition self-assemblies driven by the hydrophobic effect: synthesis and properties of a supramolecular nanocapsule
- 6 June 2008
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 32,p. 3709-3716
- https://doi.org/10.1039/b805446k
Abstract
High definition self-assemblies, those that possess order at the molecular level, are most commonly made from subunits possessing metals and metal coordination sites, or groups capable of partaking in hydrogen bonding. In other words, enthalpy is the driving force behind the free energy of assembly. The hydrophobic effect engenders the possibility of (nominally) relying not on enthalpy but entropy to drive assembly. Towards this idea, we describe how template molecules can trigger the dimerization of a cavitand in aqueous solution, and in doing so are encapsulated within the resulting capsule. Although not held together by (enthalpically) strong and directional non-covalent forces, these capsules possess considerable thermodynamic and kinetic stability. As a result, they display unusual and even unique properties. We discuss some of these, including the use of the capsule as a nanoscale reaction chamber and how they can bring about the separation of hydrocarbon gases.Keywords
This publication has 54 references indexed in Scilit:
- Sophistication of foldamer form and function in vitro and in vivoCurrent Opinion in Chemical Biology, 2007
- Contortions of encapsulated alkyl groupsChemical Communications, 2007
- Supramolecular Chemistry in WaterAngewandte Chemie International Edition in English, 2007
- Highly Selective Supramolecular Catalyzed Allylic Alcohol IsomerizationJournal of the American Chemical Society, 2007
- Templated Assembly of Water-Soluble Nano-Capsules: Inter-Phase Sequestration, Storage, and Separation of Hydrocarbon GasesJournal of the American Chemical Society, 2006
- Molecular Recognition and Stabilization of Iminium Ions in WaterJournal of the American Chemical Society, 2006
- Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient CatalysisScience, 2006
- Interfaces and the driving force of hydrophobic assemblyNature, 2005
- The rational design of high symmetry coordination clusters †J. Chem. Soc., Dalton Trans., 1999
- Cyclophane-arene inclusion complexation in protic solvents: solvent effects versus electron donor-acceptor interactionsJournal of the American Chemical Society, 1991