Halogenated calixpyrroles, calixpyridinopyrroles and calixpyridines, and uses thereof
First Claim
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1. A compound comprising a β
- -substituted calix[n]pyrrole macrocycle having structure I;
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Abstract
The present invention provides halogenated calixpyrrole, calixpyridinopyrrole, and calixpyridine macrocycles having 4-12 pyrrolic rings with greater stability, enhanced anion and neutral molecule binding affinity, and different binding selectivites as compared to their nonhalogenated congeners as judged from 1H NMR, 19F NMR and fluorescence emission spectroscopic analyses.
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Citations
30 Claims
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1. A compound comprising a β
- -substituted calix[n]pyrrole macrocycle having structure I;
- View Dependent Claims (2, 3, 5, 6, 7, 9, 10, 11, 13, 15, 16, 17, 19, 20, 21, 22, 23, 25, 26, 27, 29)
- -substituted calix[n]pyrrole macrocycle having structure I;
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4. A compound comprising a β
- -substituted calix[n]pyrrole macrocycle having structure I;
- -substituted calix[n]pyrrole macrocycle having structure I;
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8. A compound comprising a fluorinated calix[n]pyrrole where n is 9, 10, 11, or 12.
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12. A method of making a halogenated calix[n]pyrrole where n is 4, 5, 6, 7, 8, 9, 10, 11, or 12 comprising
reacting 3,4-dihalopyrrole and a ketone molecule for a time sufficient to produce the halogenated calix[n]pyrrole.
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14. A method of removing an anion from an environment containing the anion comprising contacting the environment with a halogenated calix[n]pyrrole where n is 4, 5, 6, 7, or 8 wherein the halogenated calix[n]pyrrole binds the anion thereby removing the anion from the environment.
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18. A method for extracting an ion pair having a cation associated with an anion from an environment containing said ion pair, the method comprising contacting the environment with an anion coextractant and a cation coextractant, wherein the anion coextractant is a calix[n]pyrrole where n is 4, 5, 6, 7, or 8, and wherein the calix[n]pyrrole binds the anion and the cation coextractant binds the cation thereby allowing for removal of the ion pair from the environment.
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24. A method for reducing or preventing corrosion on a substrate susceptible to corrosion in the presence of a corrosion-promoting anion, comprising contacting the substrate with a calix[n]pyrrole where n is 4, 5, 6, 7, or 8 wherein the calix[n]pyrrole binds the corrosion-promoting anion, thereby reducing or preventing corrosion of the substrate.
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28. A method for producing a naked cation in a solution containing said cation paired with an anion, the method comprising contacting a calix[n]pyrrole where n is 4, 5, 6, 7, or 8 with the solution, wherein the calix[n]pyrrole binds the anion thereby providing the naked cation.
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30. A compound selected from the group consisting of compounds 44, 46, 48, 50, and 52.
Specification