Redox Couples, Compositions and Uses Thereof
OwnerAmer Hammami, Benoit Marsan +2inventors
InventorsAmer Hammami, Benoit Marsan, Michel Armand, Gregory Hersant
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Abstract
There is provided a composition comprising a first compound chosen from compounds of formulas (I) and (III) and a second compound chosen from compounds of formulas (II) and (IV): A-S−M+ (III) A-S—S-A (IV) Various chemical entities can be used for R1 to R4, A, M, and Z. This composition can be particularly useful as a redox couple.
Claims54
A composition comprising a first compound chosen from compounds of formulas (I) and (III) and a second compound chosen from compounds of formulas (II) and (IV):
- A-S−M+ (III)
- A-S—S-A (IV)
- wherein
- R1 and R2 are the same or different and are chosen from a hydrogen atom, C1-C30 alkyl which is linear or branched and optionally halogenated, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C12 aryl, C6-C30 aralkyl, C6-C30 alkylaryl, and C1-C12 heteroaryl, C6-C30 alkylheteroaryl, and C6-C30 alkylheterocyclyl, or R1 and/or R2 is part of a polymer chain or network
- R3 and R4 are the same or different and are chosen from a hydrogen atom, C1-C30 alkyl which is linear or branched and optionally halogenated, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C12 aryl, C6-C30 aralkyl, C6-C30 alkylaryl, and C1-C12 heteroaryl, C6-C30 alkylheteroaryl, and C6-C30 alkylheterocyclyl, F, Cl, Br, I, CF3, CN, SO3H, CnF2n+1, HCnF2n+1—, CF3O, CnF2n+1O—, HCnF2n+1O—, CF3S—, CnF2n+1S—, HCnF2n+1S—ClCnF2n+1—, ClCnF2n+1O—, ClCnF2n+1S—, BrCnF2n+1—, BrCnF2n+1O—, BrCnF2n+1S—, ICnF2n+1—, ICnF2n+10, ICnF2n+1S—, CH2═CHCnF2n+1—, CH2═CHCnF2n+1—, CH2═CHCnF2n+1S—, R2OCnF2n+1—, R2OCnF2n+1O—, R2OCnF2n+1S—, CF3CH2—, CF3CH2O—, (CF3)2CH—, (CF3)2CHO—, CHF2—, CHF2O—, CHF2S—, CClF2—, CClF2O—, CClF2S—, CCl2F—, CCl2FO—, CClF2S—, CCl3—, CCl3O, C6F5—, CF3C6F4—, C6F5O—, CF3C6F4O, 3,5-(CF3)2C6H2—, C6Cl5—, C6Cl5O—, FSO2CF2—, ClSO2(CF2)n—, −SO3(CF2)n—, −CO2(CF2)n—, FSO2N(−)SO2(CF2)n—, CF3SO2N(−)SO2(CF2)n—, CnF2n+1 SO2N(−)SO2(CF2)n—, R2SO2N(−)SO2(CF2)n—, FSO2(CF2)n—, ClSO2(CF2)n—, CnF2n+1SO2N(−)(CF2)n—, and R2SO2N(−)(CF2)n— or
- R3 and/or R4 is part of a polymer chain or network, or absent
- X− is (FSO2)2N−, (CF3SO2)2N−, (C2F5SO2)2N−, (CF3SO2)3C−, CF3SO3−, CF3COO−, AsF6−, CH3COO−, (CN)2N−, (CN)3C−NO3−, 2.3HF, Cl−, Br−, I−, PF6−, BF4−, ClO4, SCN−;
- M is H, an inorganic cation, or an organic cation;
- A is a C1-C12 heteroaryl, a C1-C12 heterocyclyl, C6-C12 aryl, C6-C30 aralkyl, or C6-C30 alkylaryl
- wherein the alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, heteroaryl, alkylheteroaryl, and alkylheterocyclyl optionally includes a heteroatom in the form of —O—, ═N—, —S—, ═P—, ═(P═O), —SO—, —SO2—;
- wherein said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, heteroaryl, alkylheteroaryl, and alkylheterocyclyl being unsubstituted or substituted with 1 to 3 substituents chosen from R3, R4, F, Cl, Br, I, OH, a C1-C6 alkoxy, a C1-C6 hydroxy alkyl, NO2, CN, CF3, SO3—, CnF2n+1, C1-C12 alkyl which is linear or branched, C6-C12 aryl, CnH2n+1, Ph2P(O)—, Ph2P—, Me2P(O)—, Me2P, Ph2P(S), Me2P(S), Ph3P═N—, Me3P═N—, C6H5CpH2p—, CpH2p+1C6H4—, CpH2p+1C6H4CnH2f—, CH2═CHCpH2p—, CH2═CHC6H5—, CH2═CHC6H4CpH2p+1—, and CH2═CHCpH2pC6H4—;
- n is an integer having a value from 1 to 48;
- m is an integer having a value from 2 to 12;
- and
- p is an integer having a value from 1 to 48.
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A redox couple according to scheme 1 or scheme 2:
- wherein
- R1 and R2 are the same or different and are chosen from a hydrogen atom, C1-C30 alkyl which is linear or branched and optionally halogenated, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C12 aryl, C6-C30 aralkyl, C6-C30 alkylaryl, and C1-C12 heteroaryl, C6-C30 alkylheteroaryl, and C6-C30 alkylheterocyclyl, or R1 and/or R2 is part of a polymer chain or network
- R3 and R4 are the same or different and are chosen from a hydrogen atom, C1-C30 alkyl which is linear or branched and optionally halogenated, C3-C12 cycloalkyl, C1-C12 heterocyclyl, C2-C8 alkenyl, C2-C8 alkynyl, C6-C12 aryl, C6-C30 aralkyl, C6-C30 alkylaryl, and C1-C12 heteroaryl, C6-C30 alkylheteroaryl, and C6-C30 alkylheterocyclyl, F, Cl, Br, I, CF3, CN, SO3H, CnF2n+1, HCnF2n+1—, CF3O—, CnF2n+1O—, HCnF2n+1O—, CF3S—, CnF2+1S—, HCnF2n+1S—, ClCnF2n+1—, ClCnF2n+1O—, ClCnF2n+1S—, BrCnF2n+1—, BrCnF2n+1O—, BrCnF2n+1S—, ICnF2n+1—, ICnF2n+1O—, ICnF2n+1S—, CH2═CHCnF2n+1—, CH2═CHCnF2n+1O—, CH2═CHCnF2n+1S—, R2OCnF2n+1—, R2OCnF2n+1O—, R2OCnF2n+1S—, CF3CH2—, CF3CH2O—, (CF3)2CH—, (CF3)2CHO—, CHF2—, CHF2O—, CHF2S—, CClF2—, CClF2O—, CClF2S—, CCl2F—, CCl2FO—, CClF2S—, CCl3—, CCl3O—, C6F5—, CF3C6F4—, C6F5s—, CF3C6F4O—, 3,5-(CF3)2C6H2—, C6Cl5—, C6Cl5O—, FSO2CF2—, ClSO2(CF2)n—, SO3(CF2)n—, CO2(CF2)n—, FSO2N(−)SO2(CF2)n—, CF3SO2N(−)SO2(CF2)n—, CnF2n+1SO2N(−)SO2(CF2)n—, R2SO2N(−)SO2(CF2)n—, FSO2(CF2)n—, ClSO2(CF2)n—, —SO3(CF2)n—, CnF2n+1SO2N(−)(CF2)n—, and R2SO2N(−)(CF2)n—
- or R3 and/or R4 is part of a polymer chain or network, or absent
- X− is (FSO2)2N−, (CF3SO2)2N−, (C2F5SO2)2N−, (CF3SO2)3C−, CF3SO3−, CF3COO−, AsF6−, CH3COO−, (CN)2N−, (CN)3C−NO3−, 2.3HF, Cl−, Br−, I−, PF6−, BF4−, ClO4, SCN−;
- M is H, an inorganic cation, or an organic cation;
- A is a C1-C12 heteroaryl, a C1-C12 heterocyclyl, C6-C12 aryl, C6-C30 aralkyl, or C6-C30 alkylaryl
- wherein said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, heteroaryl, alkylheteroaryl, and alkylheterocyclyl optionally includes a heteroatom in the form of —O—, ═N—, —S—, ═P—, ═(P═O), —SO—, —SO2—;
- wherein said alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, aryl, aralkyl, alkylaryl, heteroaryl, alkylheteroaryl, and alkylheterocyclyl being unsubstituted or substituted with 1 to 3 substituents chosen from R3, R4, F, Cl, Br, I, OH, a C1-C6 alkoxy, a C1-C6 hydroxy alkyl, NO2, CN, CF3, SO3−, CnF2n+1, C1-C12 alkyl which is linear or branched, C6-C12 aryl, CnH2n+1, Ph2P(O)—, Ph2P—, Me2P(O)—, Me2P, Ph2P(S), Me2P(S), Ph3P═N—, Me3P═N—, C6H5CpH2p—, CpH2p+1C6H4—, CpH2p+1C6H4CnH2f—, CH2═CHCpH2p—, CH2═CHC6H5—, CH2═CHC6H4CpH2p+1—, and CH2═CHCpH2pC6H4—;
- n is an integer having a value from 1 to 48;
- m is an integer having a value from 2 to 12;
- and
- p is an integer having a value from 1 to 48.
Dependencies are inferred from the claim text.