Proton Conduction in Tröger’s Base-Linked Poly(crown ether)s

Patel, Hasmukh A.; Selberg, John; Salah, Dhafer; Chen, Haoyuan; Liao, Yijun; Mohan Nalluri, Siva Krishna; Farha, Omar K.; Snurr, Randall Q.; Rolandi, Marco; Stoddart, J. Fraser

doi:10.1021/acsami.8b05532

Title: Proton Conduction in Tröger’s Base-Linked Poly(crown ether)s

Journal Article · Tue Jun 05 00:00:00 EDT 2018 · ACS Applied Materials and Interfaces

DOI:https://doi.org/10.1021/acsami.8b05532· OSTI ID:1460890

; Selberg, John ^[1]; Salah, Dhafer ^[2];

; Liao, Yijun;

;

^[1];

Department of Electrical Engineering, University of California Santa Cruz, Santa Cruz, California 95064, United States
King Abdulaziz City for Science and Technology (KACST), Riyadh 11442, Saudi Arabia

Exactly 50 years ago, the ground-breaking discovery of dibenzo[18]crown-6 (DB18C6) by Charles Pedersen led to the use of DB18C6 as a receptor in supramolecular chemistry and a host in host–guest chemistry. We have demonstrated proton conductivity in Tröger’s base-linked polymers through hydrogen-bonded networks formed from adsorbed water molecules on the oxygen atoms of DB18C6 under humid conditions. Tröger’s base-linked polymers—poly(TBL-DB18C6)-t and poly(TBL-DB18C6)-c—synthesized by the in situ alkylation and cyclization of either trans- or cis-di(aminobenzo) [18]crown-6 at room temperature have been isolated as high-molecular-weight polymers. The macromolecular structures of the isomeric poly(TBL-DB18C6)s have been established by spectroscopic techniques and size-exclusion chromatography. The excellent solubility of these polymers in chloroform allows the formation of freestanding membranes, which are thermally stable and also show stability under aqueous conditions. The hydrophilic nature of the DB18C6 building blocks in the polymer facilitates retention of water as confirmed by water vapor adsorption isotherms, which show a 23 wt % water uptake. The adsorbed water is retained even after reducing the relative humidity to 25%. The proton conductivity of poly(TBL-DB18C6)-t, which is found to be 1.4 × 10^–4 mS cm^–1 in a humid environment, arises from the hydrogen bonding and the associated proton-hopping mechanism, as supported by a modeling study. In addition to proton conductivity, the Tröger’s base-linked polymers reported here promise a wide range of applications where the sub-nanometer-sized cavities of the crown ethers and the robust film-forming ability are the governing factors in dictating their properties.

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Research Organization:: Northwestern Univ., Evanston, IL (United States); University of California, Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

Grant/Contract Number:: FG02-08ER15967; AC02-05CH11231; 1648815

OSTI ID:: 1460890

Alternate ID(s):: OSTI ID: 1508803

Journal Information:: ACS Applied Materials and Interfaces, Journal Name: ACS Applied Materials and Interfaces Vol. 10 Journal Issue: 30; ISSN 1944-8244

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 25 works

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