Perfluorinated amide salts and their uses as ionic conducting materials

Abstract

The invention concerns ionic compounds in which the anionic load has been delocalized. A compound disclosed by the invention is comprised of an amide or one of its salts, including an anionic portion combined with at least one cationic portion M +m in sufficient numbers to ensure overall electronic neutrality; is the compound is further comprised of M as a hydroxonium, a nitrosonium NO + , an ammonium —NH 4 +, a metallic cation with the valence m, an organic cation with the valence m, or an organometallic cation with the valence m. The anionic portion matches the formula R F —SO x —N-Z, wherein R F is a perfluorinated group, x is 1 or 2, and Z is an electroattractive substituent. The compounds can be used notably for ionic conducting materials, electronic conducting materials, colorants, and the catalysis of various chemical reactions.

1 . Ionic compound consisting of an amide or salts thereof, comprising an anionic part associated with at least one cationic part M +m   in sufficient number to ensure an electronic neutrality thereto, characterized in that M is a hydroxonium, a nitrosonium NO + , an ammonium —NH 4   + , a metallic cation having a valency m, an organic cation having a valency m or an organo-metallic cation having a valency m, an organic cation having a valency m or an organo-metallic cation having a valency m and in that the anionic part corresponds to the formula R F —SO x —N − Z in which: 
 the group —S(O) x  represents a sulfonic group —SO 2 — or a sulfinyl group —SO—;    R F  is a halogen or a perhalogenated alkyl, alkylaryl, oxa-alkyl, aza-alkyl or thia-alkyl radical, or a radical corresponding to one of the formulae R A CF 2 —, R A CF 2 CF 2 —, R A CF 2 CF(CF 3 )— or CF 3 C(R A )F— in which R A — represents a non-perhalogenated organic radical;    Z represents an electro-attractor radical having a Hammett parameter at least equal to that of a phenyl radical, selected from:    j) —CN, —NO 2 , —SCN, —N 3 , —CF 3 , R′ F CH 2 — (R′ F  being a perflourinated radical), flouroalkyloxy, flouroalkylthioxy radical,    jj) radicals comprising one or more aromatic nuclei possibly containing at least one hydrogen, oxygen, sulfur or phosphorus atom, said nuclei possibly being condensed nuclei and/or said nuclei possibly carrying at least one substituent selected from halogens, —CN, —NO 2 , —SCN, —N 3 , —CF 3 , CF 3 CH 2 —, CF 2 ═CF—O—, CF 2 ═CF—S—, perflouroalkyl groups, flouroalkyloxy groups, flouroalkylthioxy groups, alkyl, alkenyl, oxa-alkyl, oxa-alkenyl, aza-alkyl, aza-alkenyl, thia-alkyl, thia-alkenyl radicals, polymer radicals, radicals having at least one cationic ionophoric group and/or at least one anionic ionophoric group;    with the proviso that a substituent Z may be a monovalent radical, part of a multivalent radical carrying a plurality of groups R F —S(O), —N—, or a polymer segment; or    Z is a radical R D —Y— in which Y is a sulfonyl, sulfinyl or phosphonyl group and R D  is a radical selected from the group consisting of:    a) alkyl or alkenyl radicals, aryl, arylalkyl, alkylaryl or alkenylaryl radicals, alicyclic or heterocyclic radicals, including polycyclic radicals;    b) alkyl or alkenyl radicals comprising at least one functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate group;    c) aryl, arylalkyl, arylalkenyl, alkylaryl or alkenylaryl radicals, in which the aromatic nuclei and/or at least one substituent of the nucleus comprises heteroatoms such as nitrogen, oxygen, sulfur;    d) radicals comprising condensed aromatic cycles which possibly comprise at least one heteroatom selected from nitrogen, oxygen, sulfur;    e) halogenated alkyl, alkenyl, aryl, arylalkyl, alkylaryl or alkenylaryl radicals in which the number of carbon atoms carrying at least one halogen is at least equal to the number of non-halogenated carbon atoms, the carbon in a position of group Y not being halogenated when Y is —SO 2 —, said radicals possibly comprising functional ether, thioether, amine, imine, carboxyl, carbonyl, hydroxy, silyl, isocyanate or thioisocyanate groups;    f) radicals R C C(R′)(R″)—O— in which R C  is an alkyl perfluorinated radical and R′ and R″ are independently from one another, an hydrogen atom or a radical as defined in a), b), c) or d) above;    g) radicals (R B ) 2 N—, in which the R B , identical or different, are such as defined in a), b), c), d) or e) above, one of the R B  may be a hydrogen atom, or the two radicals R B  together form a bivalent radical which forms a cycle with N;    h) radicals consisting of a polymer chain;    i) radicals having one or more cationic ionophoric groups and/or one or more anionic ionophoric groups;    with the proviso that a substituent R D  may be a monovalent radical, part of a multivalent radical carrying a plurality of groups R F —S(O) x —N—Y—, or a segment of a polymer;    with the proviso that, when Y is a sulfonyl or a carbonyl, and R D  is a radical such as defined in a), R F  is R A CF 2 —, R A CF 2 CF 2 —, R A CF 2 CF(CF 3 )—, CF 3 C(R A )F— or a perhaloalkyl radical having 1 to 2 carbon atoms.    
     
     
         2 .- 78 . (canceled)