Switchable container molecules: Synthesis and reversibly controllable formation of inclusion compounds

ORGN 459

Thomas Gottschalk, gottschalk@org.chem.ethz.ch, Bernhard Jaun, and François Diederich, diederich@org.chem.ethz.ch. Laboratorium für Organische Chemie, ETH Zürich, Hoenggerberg, HCI, Zürich, 8093, Switzerland
Reversible switching between a closed conformation and an open form is the key property of two novel container molecules, a molecular basket and a molecular tube. In the closed form, they encapsulate cycloalkanes such as cyclohexane whereas upon acid-triggered switching to the open form, their binding capabilities are completely turned off. Upon neutralization, the containers return to their closed conformations and guest binding is restored at full strength. Here we describe the design, synthesis, and switchable guest-hosting properties of these novel compounds, which are based on the resorcin[4]arene platform. Furthermore we report on thermodynamic and kinetic investigations into their host-guest complexation-decomplexation equilibria.

 

New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Sci-Mix

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007