Switching of chiral induction in helical aromatic oligoamides using solid state-solution state equilibrium

J Am Chem Soc. 2004 Feb 4;126(4):1034-5. doi: 10.1021/ja039511m.

Abstract

The introduction of an R asymmetric center in an aromatic oligoamide that adopts stable helical conformations leads to a significant shift of the equilibrium between the right-handed and left-handed helices in solution: the R-P and R-M helices are diastereoisomers. However, these two species were found to cocrystallize in 1:1 proportions. Thus the chiral induction observed in solution is switched off in the solid state. This phenomenon represents an original and unexpected means to control handedness in helical oligomers.