Velcrands with snaps and their conformational control

Citation
Fc. Tucci et al., Velcrands with snaps and their conformational control, CHEM-EUR J, 6(6), 2000, pp. 1007-1016
Citations number
32
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
09476539 → ACNP
Volume
6
Issue
6
Year of publication
2000
Pages
1007 - 1016
Database
ISI
SICI code
0947-6539(20000317)6:6<1007:VWSATC>2.0.ZU;2-9
Abstract
A novel class of self-folding velcrands was prepared that dimerize through intermolecular forces. Solvophobic interactions on extended pi surfaces sta bilize the dimer similar to velcrands, while eight hydrogen bonds act like snaps to hold the molecules together. The self-complementary array of hydro gen bonding sites were incorporated on the upper rim of a resorcinarene-bas ed cavitand. A dramatic reorganization of shape and size of the internal ca vity was manifested through changes in solvent polarity. Specifically, the equilibrium between the extended surface (D-2d symmetry) and a deep cavity (C-4v symmetry) could be manipulated in mixtures of aromatic solvents (or C DCl3) and [D-6]DMSO. The switching of conformations and the dimerization mo tif are well-suited for the assembly of noncovalent polymeric materials.