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US 2025/0034092 A1Published application
Pyridinium Compounds With Low Reduction Potentials And Persistent Radical States
AssigneeBoard of Trustees of Michigan State University
InventorsThomas F. Guarr, David Patrick Hickey
Life of this patent
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Abstract
A series of pyridinium compounds have a low reduction potential and a highly persistent radical state are generally 2,6-dialkyl-4-arylpyridinum compounds and are utilized as anolytes in redox flow, thin-film metal-organic hybrid and all-organic batteries. Associated routes for synthesizing these pyridinium compounds from pyrylium intermediates are also disclosed.
Claims14
A pyridinium compound according to formula (1B):
- wherein:
- R1 and R5 are independently selected from hydrogen, a methyl group, an ethyl group, a halide group, a halomethyl group, a perhalomethyl group, an alkoxy group, a nitrile group and a nitro group;
- R2, R3 and R4 are independently selected from hydrogen, an unbranched alkyl group, a branched alkyl group, a haloalkyl group, an aralkyl group, an alkyl ether group, a nitro group, a nitrile group, a halide group, an acetyl group, a trialkylammonium alkyl group, an alkyl carboxylate group, an alkyl sulfonate group, and an alkyl phosphonate group;
- R6 and R10 are independently selected from hydrogen, a methyl group, an ethyl group, a halide group, a halomethyl group, a perhalomethyl group, a hydroxyl group, an alkoxy group, a nitrile group and a nitro group;
- R7 and R9 are independently selected from hydrogen, an unbranched alkyl group, a branched alkyl group, a haloalkyl group, a perhaloalkyl group, an aryl group, an aralkyl group, an alkyl ether group, a nitro group, a nitrile group, a halide group, an acetyl group, a trialkylammonium alkyl group, an alkyl carboxylate group, an alkyl sulfonate group, an alkyl phosphonate group, a tert-butyl group, a CF3 group, —Br, an N,N-dimethylaniline group, and an alkyl triether group;
- and
- R8 is independently selected from hydrogen, an unbranched alkyl, a branched alkyl, an alkoxy group, a haloalkyl group, a perhalomethyl group, an aryl group, an aralkyl group, an alkyl ether group, a nitro group, a nitrile group, a halide group, a trialkylammonium alkyl group, an alkyl carboxylate group, an alkyl sulfonate group, an alkyl phosphonate group, a tert-butyl group, a CF3 group, —Br, a N,N-dimethylaniline group, and an alkyl triether group,
- wherein at least one of R1-R10 is not hydrogen.
5 more elements
A pyridinium compound according to formula (1C):
- wherein:
- R1 and R5 are independently selected from hydrogen, a methyl group, an ethyl group, a halide group, a halomethyl group, a hydroxyl group, an alkoxy group, a methoxy group, a nitrile group and a nitro group;
- R2, R3 and R4 are independently selected from hydrogen, an unbranched alkyl group, a branched alkyl group, an alkoxy group, a methoxy group, a haloalkyl group, an aryl group, an aralkyl group, an alkyl ether group, a nitro group, a nitrile group, a halide group, an acetyl group, a trialkylammonium alkyl group, an alkyl carboxylate group, an alkyl sulfonate group, and an alkyl phosphonate group;
- and
- R′ is selected from an unbranched alkyl group, a branched alkyl group, a haloalkyl group, an aralkyl group, an alkyl ether group, an alkyl nitro group, an alkyl nitrile group, a trialkylammonium alkyl group, an alkyl carboxylate group, an alkyl sulfonate group, and an alkyl phosphonate group,
- wherein when at least one of R1, R2, R3, R4 and R5 is the methoxy group, R′ includes two carbons or more, and
- wherein at least one of R1 or R5 is not hydrogen.
4 more elements
(canceled)
A pyridinium compound selected from the group consisting of:
Dependencies are inferred from the claim text.