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Wright AG, Weissbach T, Holdcroft S. Poly(phenylene) and m-Terphenyl as Powerful Protecting Groups for the Preparation of Stable Organic Hydroxides. Angew Chem Int Ed Engl. 2016;55(15):4818-21doi: 10.1002/anie.201511184.
Wright, A. G., Weissbach, T., & Holdcroft, S. (2016). Poly(phenylene) and m-Terphenyl as Powerful Protecting Groups for the Preparation of Stable Organic Hydroxides. Angewandte Chemie (International ed. in English), 55(15), 4818-21. https://doi.org/10.1002/anie.201511184
Wright, Andrew G, et al. "Poly(phenylene) and m-Terphenyl as Powerful Protecting Groups for the Preparation of Stable Organic Hydroxides." Angewandte Chemie (International ed. in English) vol. 55,15 (2016): 4818-21. doi: https://doi.org/10.1002/anie.201511184
Wright AG, Weissbach T, Holdcroft S. Poly(phenylene) and m-Terphenyl as Powerful Protecting Groups for the Preparation of Stable Organic Hydroxides. Angew Chem Int Ed Engl. 2016 Apr 04;55(15):4818-21. doi: 10.1002/anie.201511184. Epub 2016 Mar 07. PMID: 26948285.
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Angew Chem Int Ed Engl. 2016 Apr 04;55(15):4818-21. doi: 10.1002/anie.201511184. Epub 2016 Mar 07.

Poly(phenylene) and m-Terphenyl as Powerful Protecting Groups for the Preparation of Stable Organic Hydroxides.

Angewandte Chemie (International ed. in English)

Andrew G Wright, Thomas Weissbach, Steven Holdcroft

Affiliations

  1. Department of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6, Canada.
  2. Department of Chemistry, Simon Fraser University, 8888 University Dr., Burnaby, BC, V5A 1S6, Canada. [email protected].

PMID: 26948285 DOI: 10.1002/anie.201511184

Abstract

Four benzimidazolium hydroxide compounds, in which the C2-position is attached to a phenyl group possessing hydrogen, bromine, methyl groups, or phenyl groups at the ortho positions, are prepared and investigated for stability in a quantitative alkaline stability test. The differences between the stability of the various protecting groups in caustic solutions are rationalized on the basis of their crystal structures and DFT calculations. The highest stability was observed for the m-terphenyl-protected benzimidazolium, showing a half-life in 3 M NaOD/CD3OD/D2O at 80 °C of 3240 h. A high-molecular-weight polymer analogue of this model compound is prepared that exhibits excellent mechanical properties, high ionic conductivity and ion-exchange capacity, as well as remarkable hydroxide stability in alkaline solutions: only 5% degradation after 168 h in 2 M KOH at 80 °C. This is the most stable hydroxide-conducting benzimidazolium polymer to date.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: alkaline stability; anion exchange membranes; benzimidazolium; fuel cells; nitrogen heterocycles

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