Heterocyclic aromatic anion salts, and their uses as ionic...

Details Heterocyclic aromatic anion salts, and their uses as ionic... Heterocyclic aromatic anion salts, and their uses as ionic...

1998-11-19

2001-01-09

Kopec, Mark (Department: 1751)

Compositions

Electrically conductive or emissive compositions

C252S062200, C429S188000, C429S199000, C429S199000, C549S014000, C549S357000, C502S102000, C502S300000, C502S302000, C345S049000, C359S265000

Reexamination Certificate

active

06171522

ABSTRACT:

It is an object of the present invention to provide ionic compounds in which the anionic charge is delocalized, and their uses.
Derivatives of non-nucleophilic or slightly basic anions have an increasing importance in all applications of chemistry to stabilize or activate various cationic charges such as those of colouring materials or intermediate species in polymerizations. They also act as intermediates for various reactions of organic chemistry. In electrochemistry, media other than water are more and more relied upon for applications such as primary or secondary generators, supercapacitances, systems of modulation of light. The introduction of a weak ionic conductivity in the usual materials (polymers, combustible liquids), enables to disperse electrostatic charges.
Derivatives which are derived from coordination anions of the type BF
4
−
, PF
6
−
, AsF
6
−
, are mainly known, however, they have a limited stability due to dissociation equilibrium releasing the fluoride ion and the corresponding Lewis acid, both causing parasite reactions and presenting a toxicity which is not negligible. The perchlorate anion ClO
4
−
is thermally unstable and dangerous. On the other hand, anions derived from bis(perfluoroalkylsulfonyl)imides which present interesting properties are known. However, this type of chemistry is relatively difficult to control, in particular during the preparation of precursors of the type R
F
SO
2
—.
On the other hand, pyrimidinetrione (barbituric acid) and its derivatives which are obtained by replacing an atom of oxygen by an atom of sulfur (thiobarbituric acid) are known. Also known is the possibility to produce salts with 2,2-dimethyl-1,3-dioxane-4,6-dione (“Meldrum acid”). In both cases, the acids are relatively weak (pK
A
) of the order of 5 in water, of the order of 10 in dimethylsulfoxide). Their salts are neither easily soluble nor easily dissociable in organic solvents. In the case of pyrimidinetrione, the hydrogen bonds formed by the protons associated with nitrogen reinforce this insolubility. Their substitution with alkyl radicals strongly decreases the strength of the acid.
The inventors have now found that, surprisingly, the solubility and dissociation of the salts obtained from pyridiminandrione derivatives and its homologues by substitution on the carbon atom in position 5, or on the nitrogens in positions 1 and 3 is considerably increased when the substituents have an electronically attracting power. The same is true with respect to compounds derived from 1,3-dioxane-4,6-diones and their homologues which carry a substituent which is an electroattractor on carbon 2 and/or carbon 5. The choice of substituents and the numerous possible combinations in three substitution sites for each family give various materials for which it is possible to modulate the physical or chemical properties to a large extent. These compounds have interesting properties for the above-mentioned applications and their preparation calls for materials which are more readily accessible. For example, it is possible to obtain stable anionic heterocycles incorporating smaller quantities of fluorine, or to use as starting products fluorinated compounds which are easily accessible. Certain compounds may totally prevent having to rely on fluorine atoms.


REFERENCES:
patent: 5817376 (1998-10-01), Everaerts et al.

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