Molecular probe for selective detection of copper (II) ions

Patent metadata

Field	Value
Publication number	US-12172948-B2
Application number	US-202117525730-A
Country	US
Kind code	B2
Filing date	Nov 12, 2021
Priority date	Nov 12, 2020
Publication date	Dec 24, 2024
Grant date	Dec 24, 2024

Abstract

Multifunctional dendritic molecular probes that selectively detect Cu 2+ ions via potentiometric and fluorometric techniques with low detection limits are disclosed. The selective and reversible binding of the molecules with the Cu 2+ ion was used to make solid-state microsensors by incorporating the molecular probes into the carbon-based membranes as an ionophore for Cu (II).

First claim

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A compound having formula (I):

or a salt, an isomer, or tautomer thereof, wherein:
R 1 , R 2 , and R 6 are independently H, optionally substituted C1-C18 alkyl, C1-C18 optionally substituted C6-C18 aryl, or optionally substituted C5-C18 heteroaryl, and
R 3 , R 4 , and R 5 are C1-C18 alkyl substituted with a C6-C18 aryl or a C5-C18 heteroaryl.

2. The compound of claim 1 , wherein R 3 , R 4 , and R 5 are independently optionally substituted benzyl.

3. The compound of claim 1 , wherein R 3 , R 4 , and R 5 are benzyl.

4. The compound of claim 1 , wherein R 1 and R 2 are independently H, methyl, or ethyl.

5. The compound of claim 1 , wherein R 1 and R 2 are methyl and R 6 is H.

6. The compound of claim 1 , wherein the compound is:

7. A carbon-based membrane comprising a compound of claim 1 bound to the membrane.

8. The membrane of claim 7 , wherein the compound is bound covalently or non-covalently.

9. A sensor comprising the membrane of claim 7 .

10. The sensor of claim 9 , wherein the sensor is a potentiometric, fluorimetric, or colorimetric sensor.

11. The sensor of claim 9 , wherein the sensor is a potentiometric sensor with Cu2+ ion detection limit of about 3.5 μM and/or a fluorimetric sensor with Cu2+ ion detection limit of about 15 nM.

12. A Cu2+-selective electrode comprising a solid electron conductor in electrical contact with an ion-selective polymeric composition comprising a compound of claim 1 .

13. The electrode of claim 12 , wherein the solid electron conductor is a copper wire.

14. The electrode of claim 12 , wherein the ion-selective polymeric composition further comprises: (a) tetraphenyl borate, tetrakis(4-chlorophenyl) borate, tetrakis [3,4-bis(trifluoromethyl) phenyl] borate, or a combination thereof; (b) polyvinyl chloride (PVC); (c) dioctyl sebacate (DOS), 1-nitro-2-(n-octyloxy) benzene (NPOE), or a combination thereof; and (d) carbon.

15. The electrode of claim 12 , wherein the ion-selective polymeric composition further comprises tetraphenylborate, PVC, DOS, and Vulcan carbon powder.

16. A colorimetric device comprising a membrane impregnated with a compound of claim 1 .

17. The colorimetric device of claim 16 , wherein the membrane is a cellulose membrane.

18. A carbon-based membrane comprising a compound bound to the membrane, wherein the compound has formula (I):

or a salt, an isomer, or tautomer thereof, wherein:
R 1 , R 2 , and R 6 are independently H, optionally substituted C1-C18 alkyl, C1-C18 optionally substituted C6-C18 aryl, or optionally substituted C5-C18 heteroaryl, and
R 3 , R 4 , and R 5 are C1-C18 alkyl optionally substituted with a C6-C18 aryl or a C5-C18 heteroaryl.

19. The membrane of claim 18 , wherein the compound is bound covalently or non-covalently.

20. A sensor comprising the membrane of claim 18 .

21. The sensor of claim 20 , wherein the sensor is a potentiometric, fluorimetric, or colorimetric sensor.

22. The sensor of claim 20 , wherein the sensor is a potentiometric sensor with Cu2+ ion detection limit of about 3.5 μM and/or a fluorimetric sensor with Cu2+ ion detection limit of about 15 nM.

23. A Cu2+-selective electrode comprising a solid electron conductor in electrical contact with an ion-selective polymeric composition comprising a compound, wherein the compound has formula (I):

or a salt, an isomer, or tautomer thereof, wherein:
R 1 , R 2 , and R 6 are independently H, optionally substituted C1-C18 alkyl, C1-C18 optionally substituted C6-C18 aryl, or optionally substituted C5-C18 heteroaryl, and
R 3 , R 4 , and R 5 are C1-C18 alkyl optionally substituted with a C6-C18 aryl or a C5-C18 heteroaryl.

24. The electrode of claim 23 , wherein the solid electron conductor is a copper wire.

25. The electrode of claim 23 , wherein the ion-selective polymeric composition further comprises: (a) tetraphenyl borate, tetrakis(4-chlorophenyl) borate, tetrakis [3,4-bis(trifluoromethyl) phenyl] borate, or a combination thereof; (b) polyvinyl chloride (PVC); (c) dioctyl sebacate (DOS), 1-nitro-2-(n-octyloxy) benzene (NPOE), or a combination thereof; and (d) carbon.

26. The electrode of claim 23 , wherein the ion-selective polymeric composition further comprises tetraphenylborate, PVC, DOS, and Vulcan carbon powder.

27. A colorimetric device comprising a membrane impregnated with a compound, wherein the compound has formula (I):

or a salt, an isomer, or tautomer thereof, wherein:
R 1 , R 2 , and R 6 are independently H, optionally substituted C1-C18 alkyl, C1-C18 optionally substituted C6-C18 aryl, or optionally substituted C5-C18 heteroaryl, and
R 3 , R 4 , and R 5 are C1-C18 alkyl optionally substituted with a C6-C18 aryl or a C5-C18 heteroaryl.

28. The colorimetric device of claim 27 , wherein the membrane is a cellulose membrane.

Assignees

• Univ Oregon State

Inventors

• Koley Dipankar
• Sheet Partha Sarathi

Classifications

• G01N21/643

  non-biological material · CPC title

• G01N21/251

  Colorimeters; Construction thereof · CPC title

• G01N2021/6434

  Optrodes · CPC title

• G01N27/3335

  the membrane containing at least one organic component (G01N27/3271 takes precedence; aspects concerning the enzyme reagent in enzyme electrodes C12Q1/001) · CPC title

• G01N31/22

  using chemical indicators (G01N31/02 takes precedence) · CPC title