TY - JOUR
T1 - Effective Na+-Binding Ability and Molecular Assembly of an Alkylamide-Substituted Penta(ethylene)glycol Derivative
AU - Seto, Shinya
AU - Takeda, Takashi
AU - Hoshino, Norihisa
AU - Akutagawa, Tomoyuki
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research on KAKENHI (JP19H00886, JP20H05865, JP20K05442, and JP20H04655), JST CREST (grant number JPMJCR18I4), and the “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” project supported by MEXT.
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/6/17
Y1 - 2021/6/17
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.jpcb.1c03188
DO - 10.1021/acs.jpcb.1c03188
M3 - Article
C2 - 34086464
AN - SCOPUS:85108386504
VL - 125
SP - 6349
EP - 6358
JO - Journal of Physical Chemistry B
JF - Journal of Physical Chemistry B
SN - 1520-6106
IS - 23
ER -