Effective Na⁺-Binding Ability and Molecular Assembly of an Alkylamide-Substituted Penta(ethylene)glycol Derivative

A new amphiphilic penta(ethylene glycol) derivative (1) bearing two hydrogen-bonding -CONHC₁₄H₂₉ chains was prepared. Compound 1 exhibited ion-recognition abilities for Na⁺ and K⁺, and its properties were compared with those of the macrocyclic [18]crown-6. Although both compound 1 and [18]crown-6 have six ether oxygen atoms (-OC₂H₂-), the Na⁺-binding ability of the former was much higher than that of the latter. K⁺-binding ability of cyclic [18]crown-6 was much higher than its Na⁺-binding ability, while the reverse was true for acyclic compound 1. Single-crystal X-ray structural analysis of Na⁺·1·B(Ph)₄^-·(hexane)₂ at 100 K revealed the existence of a wrapped Na⁺-coordination by six ether and one carbonyl oxygen atoms of 1, which was further stabilized by intramolecular N-H···O═ hydrogen-bonding interactions. The complex phase transition during glass (G) formation and recrystallization was confirmed in the thermal cycle of Na⁺·1·B(Ph)₄^-, whose molten state showed two kinds of liquid phases, Na⁺-complexed (Na⁺·1) + B(Ph)₄^- and completely dissociated Na⁺ + 1 + B(Ph)₄^-. The Na⁺ conductivity of the molten state was 2 orders of magnitude higher than that of the G phase.