Treatment of tetraalcohol 1 with glutaroyl (2a, n = 3), adipoyl (2b, n = 4), and pimeloyl (2c, n = 5) dichlorides in the presence of Et 3N gave the corresponding double-spanned calixresorcarenes 3a-c, in which the insertion of two polymethylene bridges led to the formation of a cavity-shaped architecture resembling a basket. NMR, X-ray, and molecular dynamic studies showed that one of the two equivalent flattened-cones, which constituted the original cone conformation of 1, had been frozen in the basket derivative. In the solid state the calixarene 3b exists as a supramolecular dimer, in which one of the handles is inserted in the concave cavity of an adjacent molecule. A molecular modeling study revealed that the minimum absolute free energy was associated to the unsymmetrical type of dimer named AB-AC.
|Number of pages||7|
|Journal||Journal of Organic Chemistry|
|Publication status||Published - Dec 1 1997|
ASJC Scopus subject areas
- Organic Chemistry