Switching of Chiral Induction in Helical Aromatic Oligoamides Using Solid State−Solution State Equilibrium
2004; American Chemical Society; Volume: 126; Issue: 4 Linguagem: Inglês
10.1021/ja039511m
ISSN1943-2984
AutoresHua Jiang, Christel Dolain, Jean‐Michel Léger, Heinz Gornitzka, Ivan Huc,
Tópico(s)Chemical Synthesis and Analysis
ResumoThe 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.
Referência(s)