A Synthetic Receptor Which Uses Multiple Edge-Face Interactions To Bind Aromatic Guests

Autor: Howard W. Whitlock, Mary J. Cloninger
Rok vydání: 2001
Předmět:
Zdroj: The Journal of organic chemistry. 63(18)
ISSN: 1520-6904
Popis: Host 1 binds bicyclic aromatic guests such as 6-nitro-2-naphthol 2, serotonin mimic 3, and stilbene-derivative 4 with high affinity. Competition studies were performed to determine the association constants for complexation of 2−4 by 1. Lower-affinity host 14 lacked the structural requirements to form edge−face contacts with guests 2−4 and served as the competitive host. For each guest, evaluation of the geometry of the host−guest interaction by low-temperature NMR experiments revealed two edge−face interactions between the face of the anthracene bridge of 1 and the edge of the guest. The results reported in this paper suggest that the observed edge−face interactions stabilize the complexes formed by host 1. The synthesis of host 1 and the complexation of 2−4 by this host are described.
Databáze: OpenAIRE