Journal
CHEMICAL COMMUNICATIONS
Volume -, Issue 27, Pages 2777-2789Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b617548a
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Funding
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM050174] Funding Source: NIH RePORTER
- NIGMS NIH HHS [GM 29372, GM 50174] Funding Source: Medline
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Rotors are recalled as early molecular devices that transmit information through changes in conformation. Specific cases involve bipyridyls and biphenyls in which the biaryl bond acts as a fulcrum to relay applied stresses from one site to another. New types of molecular stress encountered by encapsulated molecules are identified - including bending, straightening, squeezing, grinding and compression. For flexible molecules in reversibly formed capsules a fluid model of recognition is proposed that is neither lock-and-key nor induced fit. Instead, the guest assumes the shape that best fills the available space, even if contortions to higher energy conformations are required. For encapsulated alkanes, a delicate balance of attraction and repulsion exists when the size of a guest molecule approaches the space available to it. The complexes are analyzed by both NMR and computational methods and detailed maps of the host - guest interfaces in solution are provided. The reversible transition of an encapsulated alkane between a compressed, coiled conformation and a relaxed, extended one is described. The system is a spring-loaded molecular device under the control of acids and bases that offers an alternative to the rotors of current molecular machinery.
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