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Velcrands with Snaps and Their Conformational Control
Author(s) -
Tucci Fabio C.,
Rudkevich Dmitry M.,
Rebek, Jr. Julius
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000317)6:6<1007::aid-chem1007>3.0.co;2-a
Subject(s) - solvophobic , resorcinarene , cavitand , chemistry , hydrogen bond , dimer , intermolecular force , non covalent interactions , molecule , folding (dsp implementation) , crystallography , solvent , self assembly , dissociation (chemistry) , molecular recognition , chemical physics , supramolecular chemistry , organic chemistry , electrical engineering , engineering
A novel class of self‐folding velcrands was prepared that dimerize through intermolecular forces. Solvophobic interactions on extended π surfaces stabilize the dimer similar to velcrands , while eight hydrogen bonds act like snaps to hold the molecules together. The self‐complementary array of hydrogen bonding sites were incorporated on the upper rim of a resorcinarene‐based cavitand. A dramatic reorganization of shape and size of the internal cavity 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 CDCl 3 ) and [D 6 ]DMSO. The switching of conformations and the dimerization motif are well‐suited for the assembly of noncovalent polymeric materials.