Aryl diazonium salt and use in an electrolytic solution of an electrochemical generator
The invention relates to a diazonium aryl salt devoid of hydroxyl functions of the following general formula (1): X −+ N≡N-A-R 1 —(OR 2 ) n —O—R 4 -A′-N≡N + X − (1) in which: n is in a range of from 1 to 10, preferably from 1 to 4, X − represents a counter-ion of the diazonium cation selected from the group consisting of halogenides, BF 4 —, NO 3 —, HSO 4 —, PF 6 —, CH 3 COO—, N(SO 2 CF 3 ) 2 —, CF 3 SO 3 —, CH 3 SO 3 —, CF 3 COO—, (CH 3 O)(H)PO 2 —, and N(CN) 2 —; R 1 , R 2 and R 4 are identical or different and are independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group, a linear alkyl group, and a branched alkyl group; and A and A′ are identical or different and independently represent a mono or polycyclic, aromatic hydrocarbonated group chosen from the group formed by phenyl, aryl groups, condensed polyaromatic groups, which may be substituted.
1. An electrolytic solution comprising:
a diazonium salt devoid of hydroxyl functions, the diazonium salt having the following general formula:
X −+ N≡N-A-R 1 —(OR 2 ) n —O—R 4 -A′-N≡N + X −
in which:
n is an integer in a range of from 1 to 10,
X— represents a counter-ion of the diazonium cation selected from the group consisting of halogenides, BF 4 —, NO 3 —, HSO 4 —, PF 6 —, CH 3 COO—, N(SO 2 CF 3 ) 2 —, CF 3 SO 3 —, CH 3 SO 3 —, CF 3 COO—, (CH 3 O)(H)PO 2 —, and N(CN) 2 —,
R 1 , R 2 and R 4 are independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group, a linear alkyl group, and a branched alkyl group; and,
A and A′ independently represent a mono or polycyclic, aromatic hydrocarbonated group chosen from the group formed by phenyl, aryl groups, condensed polyaromatic groups, which may be substituted.
2. The electrolytic solution according to claim 1 , wherein n is in a range of from 1 to 4.
3. The electrolytic solution according to claim 1 , wherein:
R 1 is independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group comprising from 1 to 6 carbon atoms, a linear alkyl group comprising from 1 to 6 carbon atoms, and a branched alkyl group comprising from 1 to 6 carbon atoms;
R 2 is independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group comprising from 2 to 6 carbon atoms, a linear alkyl group comprising from 2 to 6 carbon atoms, and a branched alkyl group comprising from 2 to 6 carbon atoms;
R 4 is independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group comprising from 2 to 8 carbon atoms, a linear alkyl group comprising from 2 to 8 carbon atoms, and a branched alkyl group comprising from 2 to 8 carbon atoms; and wherein
A and A′ independently represent a mono or polycyclic, aromatic hydrocarbonated group chosen from the group formed by phenyl, aryl groups comprising from 6 to 10 carbon atoms, condensed polyaromatic groups comprising from 10 to 45 carbon atoms, which may be substituted by one or more groups selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group comprising from 2 to 8 carbon atoms, and a branched alkyl group comprising from 2 to 8 carbon atoms.
4. The electrolytic solution according to claim 3 , wherein A and A′ independently represent a mono or polycyclic, aromatic hydrocarbonated group chosen from the group formed by phenyl, aryl groups comprising from 6 to 10 carbon atoms, condensed polyaromatic groups comprising from 10 to 45 carbon atoms, which may be substituted by one or more groups selected from the group consisting of
—H,
—CH 3 ,
a halogenide,
a linear alkyl group comprising from 2 to 8 carbon atoms and one or more heteroatoms chosen from O, S and N, and
a branched alkyl group comprising from 2 to 8 carbon atoms and one or more heteroatoms chosen from O, S and N.
5. The electrolytic solution according to claim 1 , wherein R 2 is selected from the group consisting of methylene-, ethylene-, n-propylene-, iso-propylene-, n-butylene-, tert-butyl-, sec-butylene- and n-pentylene-.
6. The electrolytic solution according to claim 1 , wherein each of R 1 and R 4 represents a —CH 2 — group.
7. The electrolytic solution according to claim 1 , wherein A and A′ are independently selected from the group consisting of phenyl, anthracenyle and naphtalenyle groups, which may be substituted.
8. The electrolytic solution according to claim 7 , wherein A and A′ are chosen independently from the phenyl, anthracenyle and naphtalenyle groups, which may be substituted by one or more groups selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group comprising from 2 to 8 carbon atoms, and a branched alkyl group comprising from 2 to 8 carbon atoms.
9. The electrolytic solution according to claim 8 , A and A′ are chosen independently from the phenyl, anthracenyle and naphtalenyle groups, which may be substituted by one or more groups selected from the group consisting of
—H,
—CH 3 ,
a halogenide,
a linear alkyl group comprising from 2 to 8 carbon atoms and one or more heteroatoms chosen from O, S, and N, and
a branched alkyl group comprising from 2 to 8 carbon atoms and one or more heteroatoms chosen from O, S and N.
10. The electrolytic solution according to claim 1 , having the following general formula:
wherein:
n is an integer in a range of from 1 to 10,
m is equal to 0 or 1,
p is an integer in a range of from 1 to 5,
X— and Y— independently represent a counter-ion of the diazonium cation selected from the group consisting of halogenides, BF 4 —, NO 3 —, HSO 4 —, PF 6 —, CH 3 COO—, N(SO 2 CF 3 ) 2 —, CF 3 SO 3 —, CH 3 SO 3 —, CF 3 COO—, (CH 3 O)(H)PO 2 —, and N(CN) 2 —,
R 1 and R 4 are independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group, a linear alkyl group, and a branched alkyl group; and
R 7 and R 8 are independently selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group optionally having one or more heteroatoms, and a branched alkyl group optionally having one or more heteroatoms.
11. The electrolytic solution according to claim 10 , wherein R 7 and R 8 are independently selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group containing one or more heteroatoms, and a branched alkyl group containing one or more heteroatoms.
12. The electrolytic solution according to claim 10 , wherein:
R 1 and R 4 are independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group comprising from 1 to 6 carbon atoms, a linear alkyl group comprising from 1 to 6 carbon atoms, and a branched alkyl group comprising from 1 to 6 carbon atoms; and
R 7 and R 8 are independently selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group comprising from 2 to 8 carbon atoms, and a branched alkyl group comprising from 2 to 8 carbon atoms.
13. The electrolytic solution according to claim 12 , wherein R 7 and R 8 are independently selected from the group consisting of
—H,
—CH3,
a halogenide,
a linear alkyl group comprising from 2 to 8 carbon atoms and having one or more heteroatoms chosen from O, S, and N, and
a branched alkyl group comprising from 2 to 8 carbon atoms and having one or more heteroatoms chosen from O, S and N.
14. The electrolytic solution according to claim 10 , having the following general formula:
in which:
n is an integer in a range of from 1 to 10,
m is equal to 0 or 1,
p is an integer in a range of from 1 to 5,
X— and Y— independently represent a counter-ion of the diazonium cation chosen from the halogenides, BF 4 —, NO 3 —, HSO 4 —, PF 6 —, CH 3 COO—, N(SO 2 CF 3 ) 2 —, CF 3 SO 3 —, CH 3 SO 3 —, CF 3 COO—, (CH 3 O)(H)PO 2 —, and N(CN) 2 —,
R 1 and R 4 are independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group, a linear alkyl group, and a branched alkyl group; and
R 7 and R 8 are independently selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group optionally having one or more heteroatoms, and a branched alkyl group optionally having one or more heteroatoms.
15. The electrolytic solution according to claim 14 , wherein R 7 and R 8 are independently selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group comprising one or more heteroatoms, and a branched alkyl group comprising one or more heteroatoms.
16. The electrolytic solution according to claim 14 , wherein:
R 1 and R 4 are independently selected from the group consisting of —CH 2 —, a cyclic alkyl group, an acyclic alkyl group comprising from 1 to 6 carbon atoms, a linear alkyl group comprising from 1 to 6 carbon atoms, and a branched alkyl group comprising from 1 to 6 carbon atoms; and
R 7 and R 8 are independently selected from the group consisting of —H, —CH 3 , a halogenide, a linear alkyl group comprising from 2 to 8 carbon atoms, and a branched alkyl group comprising from 2 to 8 carbon atoms.
17. The diazonium salt according to claim 16 , wherein R 7 and R 8 are independently selected from the group consisting of
—H,
—CH 3 ,
a halogenide,
a linear alkyl group comprising 2 to 8 carbon atoms and one or more heteroatoms chosen from O, S, and N, and
a branched alkyl group comprising from 2 to 8 carbon atoms and one or more heteroatoms chosen from O, S, and N.
18. The electrolytic solution according to claim 10 , wherein R 7 and R 8 are identical and represent —H.