IP Library Granted Patent US 10,189,864
Granted Patent B2
US 10,189,864 · App. 15/048,921 · Granted Jan 29, 2019

Metal complexes based on a bis(2-pyridylmethyl)amine-based scaffold and methods of making the same

Inventors: Carlos Valdez (San Ramon, CA); Edmond Y. Lau (Dublin, CA); Brian P. Mayer (San Francisco, CA)
Assignee: Lawrence Livermore National Security, LLC
C07F1/08A62D3/38C07D401/14C07F3/06C07F15/025C07F15/045C07F15/065A62D2101/02A62D2101/04A62D2101/26A62D2101/45
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Quick Facts
Patent No.
US 10,189,864
App. No.
15/048,921
Granted
Jan 29, 2019
Kind
B2
Abstract

A catalyst includes a bis(2-pyridylmethyl)amine-based ligand. A method of forming a catalyst, may include: reacting bis(2-pyridylmethyl)amine-based compound with a terminal azide and/or a terminal alkyne in the presence of Cu(I) to form a bis(2-pyridylmethyl)amine-based ligand. A method of using such catalysts may include neutralizing toxicity of at least one organophosphorus-based compound by reacting the organophosphorus-based compound with a bis(2-pyridylmethyl)amine-based ligand-metal complex.

Claims (25)

1. A catalyst, comprising:

a ligand comprising a bis(2-pyridylmethyl)amine group, wherein the ligand comprises at least three sp 2 nitrogen atoms and at least one sp3 nitrogen atom, and wherein the ligand has a structure selected from the group consisting of:

wherein each R is independently selected from the group consisting of: hydrogen, an ester, an alcohol, and polyethylene glycol (PEG); and

at least one metal cation complexed to the nitrogen atoms of the ligand, wherein the at least one metal cation includes one or more of: Zn 2+ , and Co 2+ .

2. The catalyst as recited in claim 1 , wherein the metal cation is Co 2+ .

3. The catalyst as recited in claim 1 , wherein the metal cation is Zn 2+ .

4. The catalyst as recited in claim 1 , comprising a hydroxyl group functionalized to the metal cation.

5. The catalyst as recited in claim 1 , wherein the ligand has the structure

and

wherein R is hydrogen.

6. The catalyst as recited in claim 1 , wherein the ligand has the structure

and

wherein R is hydrogen.

7. The catalyst as recited in claim 1 ,

wherein R is hydrogen.

8. A catalyst, comprising a ligand, wherein the ligand has a structure selected from the group consisting of:

wherein each R is independently selected from the group consisting of: hydrogen, an ester, an alcohol, and polyethylene glycol (PEG).

9. The catalyst as recited in claim 8 ,

wherein R is hydrogen.

10. The catalyst as recited in claim 8 , wherein the ligand has the structure

11. The catalyst as recited in claim 8 , wherein the ligand has the structure

12. The catalyst as recited in claim 8 , comprising at least one metal cation complexed to the ligand.

13. The catalyst as recited in claim 12 , wherein the at least one metal cation is selected from the group consisting of: Cu 2+ , Zn 2+ , Co 2+ , and Fe 2+ .

14. A method of forming a catalyst as recited in claim 1 , the method comprising:

reacting bis(2-pyridylmethyl)amine-based compound with a terminal azide or a terminal alkyne in the presence of Cu(I) to form the bis(2-pyridylmethyl)amine-based ligand.

Assignments (2)
CONFIRMATORY LICENSE (SEE DOCUMENT FOR DETAILS) Recorded Jul 15, 2022
From: LAWRENCE LIVERMORE NATIONAL SECURITY, LLC
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 060670/0682 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 19, 2016
From: VALDEZ, CARLOS; LAU, EDMOND Y.; MAYER, BRIAN P.
To: LAWRENCE LIVERMORE NATIONAL SECURITY, LLC
Reel/Frame 037780/0789 →
Continuity (1)
Related Publication 20170240569A1 · Aug 24, 2017