Dynamic combinatorial libraries based on hydrogen-bonded molecular boxes.
This article describes two different types of dynamic combinatorial libraries of host and guest molecules. The first part of this article describes the encapsulation of alizarin trimer 2a3 by dynamic mixtures of up to twenty different self-assembled molecular receptors together with the amplification and selection of the best binder. Receptors (1a-d)3.(DEB)6 are formed by the self-assembly of six diethyl barbiturate (DEB) and calix[4]arene dimelamine derivatives 1a-d by using hydrogen bonds. The largest amplification factor (2.8) for a host assembly (1a3.(DEB)6) was observed after the addition of 2a to four-component library 1a(n).1b(3-n).(DEB)6 (n=0-3). Addition of 2a to twenty-component library 1a(n).1b(m).1c(o).1d(3-(n+m+o)).(DEB)6 (n, m, o=0-3; (n+m+o)<or=3) also showed amplification of receptor 1a3.(DEB)6. The second part of this article describes the complexation of libraries of different alizarin-like guest molecules (2a-d) and the self-assembled receptor 1a3.(DEB)6. This receptor is able to template the formation of the best-fitting guest trimer.
Kerckhoffs
Jessica M C A
JM
Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands.
Mateos-Timoneda
Miguel A
MA
Reinhoudt
David N
DN
Crego-Calama
Mercedes
M
D000880:Anthraquinones / Q000737:chemistry*; D001463:Barbiturates / Q000737:chemistry*; D001665:Binding Sites; D047250:Calixarenes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011955:Receptors, Drug / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D000880:Anthraquinones; D001463:Barbiturates; D011955:Receptors, Drug; D047250:Calixarenes; C010078:alizarin; C032232:barbituric acid