期刊
ORGANOMETALLICS
卷 36, 期 20, 页码 4038-4046出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.7b00663
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资金
- ACS [56836-ND7]
- NSF [CHE-1455136]
- New York State Energy Research and Development Authority (NYSERDA) [38304]
- U.S. Department of Energy, Office of Science, and Office of Basic Energy Sciences [DE-SC0001086]
Hydroxide-stable organic cations are crucial components for ion-transport processes in electrochemical energy systems, and the tetrakis(dialkylamino)phosphonium cation is a promising candidate for this application. These phosphoniums are known to be highly resistant to alkaline media; however, very few investigations have systematically evaluated how these cations decompose in the presence of hydroxide or alkoxide anions. The excellent stability of several tetraaminophosphoniums in 2 M KOH/CH3OH at 80 C led us to design experiments for the rapid assessment of phosphonium degradation in homogeneous solution and under phase-transfer conditions. The analysis illustrated how substituents around the cation core affect both degradation pathways and rates. beta-H elimination and direct attack at the phosphorus atom are the most common degradation pathways observed in an alcoholic solvent, while alpha-H abstraction and direct attack are observed under phase-transfer conditions (PhCl and 50 wt % NaOH/H2O). The collected data provided a relative stability comparison for this family of cations to enable future design improvements and illustrated the utility of using multiple tests for degradation studies.
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