Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1994-12-19
1997-03-04
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540471, 544225, 544347, 546 2, 546 10, 546316, C07D21350, C07D21330, C07D22500, C07D24146
Patent
active
056080590
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The invention relates to ion-sensitive compounds. More particularly, the invention relates to ion-sensitive compounds comprising a receptor designed to bind anionic species by the formation of a receptor-substrate complex.
BACKGROUND OF THE INVENTION
Anion receptors comprising a plurality of quaternary amine groups are known. Examples of such compounds may be seen in P.G. Potvin and J-M Lehn, Prog. Macrocyclic Chem., 1987, 3, 214.
L .A. Summers, "The Bipyridinium Herbicides", Academic Press, New York, 1980, describes the use of certain compounds comprising diquaternary 2,2'-bipyridinium moieties in herbicidal applications.
Metal ion centres have also been utilised in systems for the recognition of anions as described in D.N. Reinhoudt, J. Am. Chem. Soc. 1992, 114, 9671-9673.
PROBLEM TO BE SOLVED BY THE INVENTION
There is a continuing need to provide new receptor compounds for a variety of applications. For example, there is a need for compounds which can be incorporated in electrochemical or optical sensors for anion determination. There is also a need for compounds which can be used in removal devices where levels of a given anion need to be kept low.
It is also desirable to provide receptor compounds which can be readily synthesised.
SUMMARY OF THE INVENTION
The ion-sensitive compounds of the invention have the formula A.sup.2+ B.sup.2- wherein A represents a cation capable of forming a receptor-substrate complex with an anion, and B represents one or more counter anions, characterised in that the cation is an anion receptor represented by the formula I ##STR2## or by the formula II ##STR3## wherein
R.sup.1 and R.sup.2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or R.sup.1 and R.sup.2 taken together with the atoms separating them represent the atoms necessary to complete a (2)-cryptand; and,
R.sup.3 and R.sup.4 are each independently H or a lower alkyl group having from 1 to 4 carbon atoms, or R.sup.3 and R.sup.4 taken together represent an ethylene bridging group.
The invention also provides a method of sensing an anion in solution by contacting the anion with a compound comprising a cation which is a receptor for the anion to form a receptor-substrate complex and sensing a detectable change which results from the formation of the complex characterised in that the compound is a compound of the invention.
ADVANTAGEOUS EFFECT OF THE INVENTION
The compounds of the invention show selectivity to anions and are useful for the electrochemical and/or optical detection of anions, especially halides and particularly chlorides.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a cyclic voltammogram of a compound of the invention.
FIG. 2 is a graph showing the fluorescence of a compound of the invention.
FIG. 3 is a .sup.1 H NMR titration curve of a compound of the invention and Cl.sup.- in CD.sub.3 CN solution.
DETAILED DESCRIPTION OF THE INVENTION
Preferably, R.sup.1 and R.sup.2 are each independently a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms e.g. methyl, ethyl, propyl, butyl, pentyl, hexyl, eicosyl. Suitable substituents include alkyloxy, aryloxy, alkylamido, arylamido, atkylsulfonamido, arylsulfonamido, dialkylamino, cyano and nitro. Specific examples of such R.sup.1 and R.sup.2 groups include butyl and methoxyethyl.
Preferably, R.sup.1 and R.sup.2 are each independently a substituted or unsubstituted phenyl group. Suitable substituents include alkyloxy, aryloxy, alkylamido, arylamido, alkylsulfonamido, arylsulfonamido, dialkylamino, cyano and nitro. A specific example of such a group is 3,4-dimethoxyphenyl.
R.sup.1 and R.sup.2 taken together with the atoms separating them may represent the atoms necessary to complete a (2)-cryptand. Preferably, the (2)-cryptand comprises two ionisable hydroxy groups. The two ionisable hydroxy groups together with the two amide protons shown in formula I and II are preferably arranged tetrahedrally with respect to each other within the cavity de
REFERENCES:
ACS Symp. Ser. vol. 537, (1994) Calvert et al, pp. 210-219 "Top-Surface Imaging".
J. Med. Chem. vol. 31, No. 24, (1993) Hale et al, "Novel Inhibitors".
J. Am. Chem. Soc. vol. 115, No. 10, (1993) Belser et al, "Supramolecular Ru / and or Os Complexes".
Beer Paul D.
Fletcher Nicholas C.
Goulden Alistair J.
Moore Christopher P.
Wear Trevor J.
Covington Raymond
Eastman Kodak Company
Everett John R.
Ivy C. Warren
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