Show simple item record

dc.contributor.authorTabor, Daniel P.
dc.contributor.authorGómez-Bombarelli, Rafael
dc.contributor.authorTong, Liuchuan
dc.contributor.authorGordon, Roy
dc.contributor.authorAziz, Michael
dc.contributor.authorAspuru-Guzik, Alán
dc.date.accessioned2021-04-21T15:13:47Z
dc.date.issued2019
dc.identifier.citationTabor, Daniel P., Rafael Gómez-Bombarelli, Liuchuan Tong, Roy G. Gordon, Michael J. Aziz, and Alán Aspuru-Guzik. “Mapping the Frontiers of Quinone Stability in Aqueous Media: Implications for Organic Aqueous Redox Flow Batteries.” Journal of Materials Chemistry A 7, no. 20 (2019): 12833–41. https://doi.org/10.1039/c9ta03219c.en_US
dc.identifier.issn2050-7488en_US
dc.identifier.issn2050-7496en_US
dc.identifier.urihttps://nrs.harvard.edu/URN-3:HUL.INSTREPOS:37367355*
dc.description.abstractQuinone–hydroquinone pairs have been proposed as biologically-inspired, low-cost redox couples for organic electrolytes for electrical energy storage, particularly in aqueous redox flow batteries. In their oxidized form, quinones are electrophiles that can react with the nucleophilic water solvent resulting in loss of active electrolyte. Here we study two mechanisms of nucleophilic addition of water, one reversible and one irreversible, that limit quinone performance in practical flow batteries. Using a combination of density functional theory and semi-empirical calculations, we have quantified the source of the instability of quinones in water, and explored the relationships between chemical structure, electrochemical reduction potential, and decomposition or instability mechanisms. The importance of these mechanisms was further verified through experimental characterization of a family of alizarin-derived quinones. Finally, ∼140 000 prospective quinone pairs (over 1 000 000 calculations including decomposition products) were analyzed in a virtual screening using the learned design principles. Our conclusions suggest that numerous low reduction potential molecules are stable with respect to nucleophilic addition, but promising high reduction potential molecules are much rarer. This latter fact suggests the existence of a stability cliff for this family of quinone-based organic molecules, which challenges the development of all-quinone aqueous redox flow batteries.en_US
dc.language.isoen_USen_US
dc.publisherRoyal Society of Chemistry (RSC)en_US
dash.licenseMETA_ONLY
dc.subjectRenewable Energy, Sustainability and the Environmenten_US
dc.subjectGeneral Materials Scienceen_US
dc.subjectGeneral Chemistryen_US
dc.titleMapping the Frontiers of Quinone Stability in Aqueous Media: Implications for Organic Aqueous Redox Flow Batteriesen_US
dc.typeJournal Articleen_US
dc.description.versionVersion of Recorden_US
dc.relation.journalJournal of Materials Chemistry Aen_US
dash.depositing.authorAziz, Michael
dc.date.available2021-04-21T15:13:47Z
dash.affiliation.otherHarvard John A. Paulson School of Engineering and Applied Sciencesen_US
dc.identifier.doi10.1039/c9ta03219c
dc.source.journalJ. Mater. Chem. A
dash.source.volume7;20
dash.source.page12833-12841
dash.contributor.affiliatedTong, Liuchuan
dash.contributor.affiliatedGordon, Roy
dash.contributor.affiliatedAziz, Michael


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record