Self-assembly of chiral depsipeptide dendrimers.
The self-assembly of chiral depsipeptide dendrons 4, which contain a cyanuric acid building block at their focal point, with the homotritopic Hamilton receptor 1 is reported. The 1:3 compositions of the resulting chiral supramolecular dendrimers, the association constants K(n), and the cooperativity of binding expressed by Scatchard plots and the Hill coefficients n(H) was determined by NMR titration experiments. The most pronounced positive cooperativity was found for the complexes 1 L(3) with L being the second-generation dendrons 4 c-e. The least stable complexes are formed with the bulky third-generation dendrons 4 f-h. Similar results are obtained by the corresponding complexation of the achiral Frechét-type first- to third-generation dendrons 3 with 1. Chiroptical investigations of 1:3 complexes of 1 and 4 reveal chirality transfer from the dendron to the Hamilton receptor as demonstrated by the appearance of new CD absorption bands at 310 nm.
Institut für Organische Chemie der Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany.
Kristine
K
Hager
Alexander
A
Franz
Andreas
A
Hirsch
D001665:Binding Sites; D002942:Circular Dichroism; D020650:Combinatorial Chemistry Techniques; D050091:Dendrimers / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D013237:Stereoisomerism; D014227:Triazines / Q000737:chemistry*
D050091:Dendrimers; D047630:Depsipeptides; D014227:Triazines; C004632:cyanuric acid