F⋅⋅⋅HN Hydrogen Bonding Driven Foldamers: Efficient Receptors for Dialkylammonium Ions

Abstract

Intramolecular F⋅⋅⋅HN hydrogen bonds have been utilized for the first time to construct a new series of foldamers from aromatic amides (see picture; R1=H, Me; R2=CON(n‐C8H17)2). Moreover, the resulting crescent and helical architectures are good acceptors for binding dialkylammonium ions.

Self-assembly of vesicles from the stacking of a dipodal F⋯H–N hydrogen bonded arylamide foldamer

“…11 More recently, we found that this series of folded and related macrocyclic frameworks can stack with fullerenes and coronene more strongly than the (Me)O/H-N hydrogen bonded arylamide counterparts, 12 because the ether methyl groups in the latter system have an important steric hindrance for any intermolecular stacking. Considering that several (Me)O/H-N hydrogen bonding-induced arylamide foldamers have been revealed to assemble into vesicles or organogels in polar organic solvents, 13 we became interested in designing new F/H-N hydrogen bonding-induced foldamers to produce vesicular structures, because the self-stacking of this series of frameworks might be stronger than their (Me)O/H-N hydrogen bonding-induced analogs.…”

Complexation of two non-fully hydrogen bonded aromatic hydrazide heptamers toward n-octyl-α-L-glucopyranoside in chloroform

“…However, studies on the recognition behavior of linear receptors were reported in 1970s, while Vögtle et al reported the complexing properties of oligo(ethylene glycol) derivatives toward metal ions [6] . More recently, the present authors and Huc et al found that rationally designed hydrogen bonded aromatic amide or hydrazide-based foldamers could bind neutral or ionic guests in more selective manner [7][8][9][10][11][12][13][14][15] , which mainly depends on the size of their cavity, through multiple intermolecular hydrogen bonds. For all the reported oligomers, the presence of a successive network of intramolecular hydrogen bonds forces the backbones to adopt well-predicted folded or helical conformations, which significantly reduces the binding-initiated negative entropy.…”

Hydrogen bonded foldamer-bridged biscoumarins: A UV-Vis absorption and fluorescent study of the solvent effect

“…Compound 2 was prepared from compounds 14 and 15 [17] by using a procedure similar to that for 1. 1 13 …”