Chemical sensors of zinc, nickel, and copper ions
View Patent ↗The present technology provides a dual chemical sensor for zinc and nickel ions and a chemical sensor for copper ions. Also provided are methods of making and using the chemical sensors. The chemical sensors have the structure of formula I, wherein R 1 , and R 2 are defined as set forth herein.
1. A compound of Formula I:
or salts thereof, wherein
each R 1 independently is
wherein X is —CH 2 — or is absent, and each R 2 is independently a C 3-6 straight, branched or cyclic alkyl group.
2. The compound of claim 1 , wherein each R 2 is a t-butyl.
3. The compound of claim 1 wherein X is CH 2 .
4. The compound of claim 1 wherein X is absent.
5. A complex comprising a compound of claim 1 and a Zn 2+ ion.
6. A complex comprising a compound of claim 1 and a Ni 2+ ion.
7. A complex comprising a compound of claim 1 and a Cu 2+ ion.
8. A method of testing a sample for the presence of Zn 2+ ions, Ni 2+ ions, or a mixture thereof comprising:
combining a compound of claim 1 , wherein X is absent, with a test sample, and
detecting a fluorescence of the test sample,
wherein an increase in the fluorescence of the test sample upon combination with said compound indicates the presence of Zn 2+ ions in the test sample and a decrease in the fluorescence of the test sample upon combination with said compound indicates the presence of Ni 2+ ions in the test sample.
9. The method of claim 8 further comprising comparing the detected fluorescence of the test sample with a fluorescence of a control sample, wherein an increase in the fluorescence of the test sample relative to the control sample indicates the presence of Zn 2+ ions in the test sample and a decrease in the fluorescence of the test sample relative to the control sample indicates the presence of Ni 2+ ions in the test sample.
10. The method of claim 8 , wherein the test sample is an alcoholic solution.
11. The method of claim 10 , wherein the alcoholic solution comprises methanol or ethanol.
12. The method of claim 11 , wherein the method selectively detects the presence of Zn 2+ ions or Ni 2+ ions in the presence of one or more additional divalent metal ions.
13. The method of claim 12 , wherein the one or more additional divalent metal ions are selected from the group consisting of Co 2+ , Cd 2+ , Cu 2+ , Fe 2+ , Hg 2+ , and Mn 2+ .
14. The method of claim 8 wherein the test sample includes a mixture of Ni 2+ and Zn 2+ ions in which the amount of Ni 2+ ions is at least ten times the amount of Zn 2+ ions or the amount of Zn 2+ ions is at least ten times the amount of Ni 2+ ions.
15. A method of testing a sample for the presence of Cu 2+ ions, comprising:
combining a compound of claim 1 , wherein X is CH 2 , with a test sample, and
detecting a fluorescence of the test sample,
wherein an increase in the fluorescence of the test sample upon combination with said compound indicates the presence of Cu 2+ ions in the test sample.
16. The method of claim 15 further comprising comparing the detected fluorescence of the test sample with the fluorescence of a control sample, wherein an increase in the fluorescence of the test sample relative to the control sample indicates the presence of Cu 2+ ions in the test sample.
17. The method of claim 16 , wherein the test sample or the control sample is an alcoholic solution.
18. The method of claim 17 , wherein the method selectively detects the presence of Cu 2+ ions in the presence of one or more additional mono- or divalent metal ions.
19. The method of claim 18 , wherein the one or more additional divalent metal ions are selected from the group consisting of Na + , K + , Ca 2+ , Mg 2+ , Mn 2+ , Co 2+ , Fe 2+ , Hg 2+ , Ni 2+ , Zn 2+ , and Mn 2+ ions.
20. A method for preparing a compound of claim 1 comprising contacting 2,2′-dipyridylamine or bis(pyridin-2-ylmethyl)amine in a presence of a suitable base and a solvent with a compound of Formula II:
wherein R 3 is —CH 2 COX and X is a halide.