Abstract
The implementation of redox active organics in nonaqueous redox flow batteries requires the design of molecules that exhibit high solubility (>1 M) in all battery-relevant redox states. Methods for forecasting nonaqueous solubility would be valuable for streamlining the identification of promising structures. Herein we report the development of a workflow to parametrize and predict the solubility of conformationally flexible tris-(dialkylamino)cyclopropenium (CP) radical dications. A statistical model is developed through training on monomer species. Ultimately, this model is used to predict new monomeric and dimeric CP derivatives with solubilities of >1 M in acetonitrile in all oxidation states. The most soluble CP monomer exhibits high stability to electrochemical cycling at 1 M in acetonitrile without a supporting electrolyte in a symmetrical flow cell.
Original language | English |
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Pages (from-to) | 10171-10176 |
Number of pages | 6 |
Journal | Journal of the American Chemical Society |
Volume | 141 |
Issue number | 26 |
DOIs | |
Publication status | Published - 3 Jul 2019 |
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Developing a predictive solubility model for monomeric and oligomeric cyclopropenium-based flow battery catholytes. / Robinson, Sophia G.; Yan, Yichao; Hendriks, Koen H.; Sanford, Melanie S.; Sigman, Matthew S. (Corresponding author).
In: Journal of the American Chemical Society, Vol. 141, No. 26, 03.07.2019, p. 10171-10176.Research output: Contribution to journal › Article › Academic › peer-review
TY - JOUR
T1 - Developing a predictive solubility model for monomeric and oligomeric cyclopropenium-based flow battery catholytes
AU - Robinson, Sophia G.
AU - Yan, Yichao
AU - Hendriks, Koen H.
AU - Sanford, Melanie S.
AU - Sigman, Matthew S.
PY - 2019/7/3
Y1 - 2019/7/3
N2 - The implementation of redox active organics in nonaqueous redox flow batteries requires the design of molecules that exhibit high solubility (>1 M) in all battery-relevant redox states. Methods for forecasting nonaqueous solubility would be valuable for streamlining the identification of promising structures. Herein we report the development of a workflow to parametrize and predict the solubility of conformationally flexible tris-(dialkylamino)cyclopropenium (CP) radical dications. A statistical model is developed through training on monomer species. Ultimately, this model is used to predict new monomeric and dimeric CP derivatives with solubilities of >1 M in acetonitrile in all oxidation states. The most soluble CP monomer exhibits high stability to electrochemical cycling at 1 M in acetonitrile without a supporting electrolyte in a symmetrical flow cell.
AB - The implementation of redox active organics in nonaqueous redox flow batteries requires the design of molecules that exhibit high solubility (>1 M) in all battery-relevant redox states. Methods for forecasting nonaqueous solubility would be valuable for streamlining the identification of promising structures. Herein we report the development of a workflow to parametrize and predict the solubility of conformationally flexible tris-(dialkylamino)cyclopropenium (CP) radical dications. A statistical model is developed through training on monomer species. Ultimately, this model is used to predict new monomeric and dimeric CP derivatives with solubilities of >1 M in acetonitrile in all oxidation states. The most soluble CP monomer exhibits high stability to electrochemical cycling at 1 M in acetonitrile without a supporting electrolyte in a symmetrical flow cell.
UR - http://www.scopus.com/inward/record.url?scp=85069264428&partnerID=8YFLogxK
U2 - 10.1021/jacs.9b04270
DO - 10.1021/jacs.9b04270
M3 - Article
C2 - 31203608
AN - SCOPUS:85069264428
VL - 141
SP - 10171
EP - 10176
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 26
ER -