Supramolecular Assemblies of Chiral Propargylic Alcohols

摘要

Chiral propargylic alcohols are very useful synthetic precursors to many organic compounds.[1] A few propargylic alcohols were also found to form interesting supramolecular structures through intermolecular interactions of the hydroxy groups and the electrons of the CC bonds.[2]-[4] Another supramolecular interaction based on the quadrupole - attraction between an aryl and a perfluoroaryl moiety was used to create new materials for applications in solid-state photopolymerization, liquid crystals, hydrogels, and so forth.[5] We have initiated a program to combine the four functional groups, including the aryl, perfluoroaryl, CC, and OH groups, to make the diaryl-substituted chiral propargylic alcohols and to explore their potential in supramolecular chemistry. Herein, we present some of findings that indicate that the presence of the functional groups not only makes the self-assembly of propargylic alcohols possible but it also allows for a finely tuned cooperation of interactions on a scale rarely seen in other supramolecular systems. We show herein that diaryl-substituted chiral propargylic alcohols can form cyclic hexameric supramolecular assemblies as a result of the cooperation between three major intermolecular forces: OHO hydrogen bonding, CHFC hydrogen bonding involving organic fluorine atoms, and - stacking interactions between the pentafluorophenyl and phenyl rings. We believe that this synergy of intermolecular forces could be utilized in a variety of applications, including molecular recognition and discrimination.