The chirality of dendrimer-based supramolecular complexes.
Boc-protected L-phenylalanine has been connected to a spacer-armed ureido-acetic acid derivative, which can form multiple supramolecular complexes with urea-adamantyl modified poly(propylene imine) dendrimers in chloroform. Complexes of this guest with several generations of urea-adamantyl dendrimers were prepared. The dendrimer-guest complexes were characterized in detail by (1)H-NMR, (1)H-(1)H-NOESY spectroscopy and mass spectrometry to prove their formation. Optical rotation experiments performed on different generations of dendrimer-guest complexes showed a constant positive value. These observations indicate that, though guest molecules decrease the flexibility at the periphery of the dendrimer upon binding, the amino acid at the terminus of the guest molecule retains its high local conformational freedom. This is in agreement with values found for covalently modified spacer-armed dendrimers.
Broeren
Maarten A C
MA
Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600, MB Eindhoven, The Netherlands.
de Waal
Bas F M
BF
van Dongen
Joost L J
JL
van Genderen
Marcel H P
MH
Meijer
E W
EW