US 11,056,705 B2
Organic anolyte materials for flow batteries
Melanie S. Sanford, Ann Arbor, MI (US); Christo Slavov Sevov, Ann Arbor, MI (US); Rachel Brooner, Midland, MI (US); and Etienne Chénard, Urbana, IL (US)
Assigned to THE REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US); and THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS, Urbana, IL (US)
Appl. No. 15/580,048
Filed by THE REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US); and THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS, Urbana, IL (US)
PCT Filed Jun. 8, 2016, PCT No. PCT/US2016/036336
§ 371(c)(1), (2) Date Dec. 6, 2017,
PCT Pub. No. WO2016/200870, PCT Pub. Date Dec. 15, 2016.
Claims priority of provisional application 62/221,796, filed on Sep. 22, 2015.
Claims priority of provisional application 62/172,508, filed on Jun. 8, 2015.
Prior Publication US 2018/0138539 A1, May 17, 2018
Int. Cl. H01M 8/18 (2006.01); C07D 213/55 (2006.01); C07D 213/89 (2006.01); C07F 5/02 (2006.01); H01M 4/36 (2006.01); H01M 10/0569 (2010.01); H01M 10/0567 (2010.01); H01M 2/14 (2006.01); C07D 213/56 (2006.01); C07D 213/51 (2006.01); H01M 4/90 (2006.01); H01M 50/40 (2021.01)
CPC H01M 8/188 (2013.01) [C07D 213/51 (2013.01); C07D 213/55 (2013.01); C07D 213/56 (2013.01); C07D 213/89 (2013.01); C07F 5/022 (2013.01); H01M 4/368 (2013.01); H01M 4/9008 (2013.01); H01M 10/0567 (2013.01); H01M 10/0569 (2013.01); H01M 50/40 (2021.01); H01M 2300/0028 (2013.01); Y02E 60/50 (2013.01)] 19 Claims
OG exemplary drawing
 
1. An anolyte solution for a redox flow battery comprising a non-aqueous solvent; a supporting electrolyte; and a compound of formula I as an anolyte material:

OG Complex Work Unit Chemistry
wherein
Y is selected from the group consisting of null, 0, and NR3;
Z is selected from the group consisting of N+O and N+R;
R1 is selected from the group consisting of optionally substituted C1-10 alkyl, C3-12 cycloalkyl, and optionally substituted phenyl;
R3 is an optionally substituted C1-10 alkyl; and
R is a Lewis acid.
 
2. An anolyte solution for a redox flow battery comprising a non-aqueous solvent; a supporting electrolyte; and a compound of formula Ill as an anolyte material:

OG Complex Work Unit Chemistry
wherein
R1 is selected from the group consisting of optionally substituted C1-10 alkyl, C3-12 cycloalkyl, and optionally substituted phenyl;
R2 is selected from the group consisting of methyl, ethyl, propyl, butyl, and adamantyl; and
Xis an anion.
 
10. An anolyte solution for a redox flow battery comprising a non-aqueous solvent; a supporting electrolyte; and
compound 10a as an anolyte material:

OG Complex Work Unit Chemistry