Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships | Zendy

Kristina M. Hugar | Zendy; Henry A. Kostalik | Zendy; Geoffrey W. Coates | Zendy

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Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships

Author(s) -

Kristina M. Hugar,

Henry A. Kostalik,

Geoffrey W. Coates

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b02879

Subject(s) - chemistry , cationic polymerization , substituent , chemical stability , ion exchange , inorganic chemistry , ring (chemistry) , ion , polymer chemistry , medicinal chemistry , organic chemistry

Highly base-stable cationic moieties are a critical component of anion exchange membranes (AEMs) in alkaline fuel cells (AFCs); however, the commonly employed organic cations have limited alkaline stability. To address this problem, we synthesized and characterized the stability of a series of imidazolium cations in 1, 2, or 5 M KOH/CD3OH at 80 °C, systematically evaluating the impact of substitution on chemical stability. The substituent identity at each position of the imidazolium ring has a dramatic effect on the overall cation stability. We report imidazolium cations that have the highest alkaline stabilities reported to date, >99% cation remaining after 30 days in 5 M KOH/CD3OH at 80 °C.

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