A Proton Conductive Porous Framework of an 18-Crown-6-Ether Derivative Networked by Rigid Hydrogen Bonding Modules

Xin Chen; Rui-Kang Huang; Kiyonori Takahashi; Shin-Ichiro Noro; Takayoshi Nakamura; Ichiro Hisaki

doi:10.1002/anie.202211686

A Proton Conductive Porous Framework of an 18-Crown-6-Ether Derivative Networked by Rigid Hydrogen Bonding Modules

Angew Chem Int Ed Engl. 2022 Nov 7;61(45):e202211686. doi: 10.1002/anie.202211686. Epub 2022 Oct 5.

Authors

Xin Chen¹, Rui-Kang Huang^{1

2}, Kiyonori Takahashi^{1

2}, Shin-Ichiro Noro³, Takayoshi Nakamura^{1

2}, Ichiro Hisaki^{1

2

4}

Affiliations

¹ Graduate School of Environmental Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
² Research Institute for Electronic Science, Hokkaido University, Sapporo, Hokkaido 001-0020, Japan.
³ Faculty of Environmental Earth Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
⁴ Division of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan.

PMID: 36104981
DOI: 10.1002/anie.202211686

Abstract

A rigid hydrogen-bonded organic framework (HOF) was constructed from a C₃ -symmetric hexatopic carboxylic acid with a hydrophilic 18-crown-6-ether (18C6) component. Despite the flexible macrocyclic structure with many conformations, the derivative with three 4,4'-dicarboxy-o-terphenyl moieties in the periphery yielded a rigid layered porous framework through directional intermolecular hydrogen bonding. Interestingly, the HOF possesses 1D channels with bottleneck composed of 18C6 rings. The HOF shows proton conductivity (1.12×10^-7 S cm^-1 ) through Grotthuss mechanism (E_a =0.27 eV) under 98 %RH. The present unique water channel structure provides an inspiration to create molecular porous materials.

Keywords: Crown Ether; Crystal Engineering; Hydrogen Bond; Porous Framework; Proton Conduction.

Abstract

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