Developing a predictive solubility model for monomeric and oligomeric cyclopropenium-based flow battery catholytes

Sophia G. Robinson, Yichao Yan, Koen H. Hendriks, Melanie S. Sanford, Matthew S. Sigman (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)10171-10176
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number26
DOIs
Publication statusPublished - 3 Jul 2019

Fingerprint

Solubility
Oxidation-Reduction
Acetonitrile
Monomers
Workflow
Statistical Models
Electrolytes
Derivatives
Oxidation
Molecules
Flow batteries
acetonitrile

Cite this

Robinson, Sophia G. ; Yan, Yichao ; Hendriks, Koen H. ; Sanford, Melanie S. ; Sigman, Matthew S. / Developing a predictive solubility model for monomeric and oligomeric cyclopropenium-based flow battery catholytes. In: Journal of the American Chemical Society. 2019 ; Vol. 141, No. 26. pp. 10171-10176.
@article{dd40d18acba945848889ba2096de1f5d,
title = "Developing a predictive solubility model for monomeric and oligomeric cyclopropenium-based flow battery catholytes",
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.",
author = "Robinson, {Sophia G.} and Yichao Yan and Hendriks, {Koen H.} and Sanford, {Melanie S.} and Sigman, {Matthew S.}",
year = "2019",
month = "7",
day = "3",
doi = "10.1021/jacs.9b04270",
language = "English",
volume = "141",
pages = "10171--10176",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "26",

}

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 journalArticleAcademicpeer-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 -