Porous chiral materials and uses thereof

Patent metadata

Field	Value
Publication number	US-2020009531-A1
Application number	US-201616327784-A
Country	US
Kind code	A1
Filing date	Aug 22, 2016
Priority date	Aug 22, 2016
Publication date	Jan 9, 2020
Grant date	—

Abstract

A porous chiral material of formula [M(L)1.5(A)]+X− wherein M is a metal ion; L is a nitrogen-containing bidentate ligand; A is the anion of mandelic acid or a related acid; and X− is an anion

First claim

1 . A porous chiral material of formula [M(L) 1.5 (A)] + X − wherein M is a metal ion; L is a nitrogen-containing bidentate ligand; A is the anion of mandelic acid or a related acid; and X − is an anion.

2 . A porous chiral material according to claim 1 wherein M is selected from a group consisting of: cobalt, chromium, iron, nickel, manganese, calcium, magnesium, cadmium, copper and zinc.

3 . A porous chiral material according to claim 1 wherein L is selected from a group consisting of: 4,4′-bipyridine, 1,2-bis(4-pyridyl)ethane, and 4,4′-bipyridylacetylene.

4 . A porous chiral material according to claim 1 wherein A is the anion of (S)-(−)-mandelic acid.

5 . A porous chiral material according to claim 1 wherein X − is a triflate ion.

6 . (canceled)

7 . A material of formula [M(L) 1.5 (A) + ]X − G n wherein M is a metal ion; L is a nitrogen-containing bidentate ligand; A is an anion of mandelic acid or a related acid; X − is an organic anion; G is a guest molecule; and n is from 0 to 5.

8 . (canceled)

9 . A crystalline sponge comprising a porous chiral material of formula [M(L) 1.5 (A)] + X − .

10 . A method of separating enantiomers, the method comprising contacting a composition comprising a mixture of enantiomers with a material of claim 1 .

11 . (canceled)

12 . A method of separating enantiomers according to claim 10 , the method comprising passing a composition comprising the mixture of enantiomers through a chromatography column comprising as a stationary phase a chiral porous material of formula [M(L) 1.5 (A)] + X − wherein M is a metal ion; L is a nitrogen-containing bidentate ligand; A is an anion of mandelic acid or a related acid; and X − is an anion.

13 . A method of separating enantiomers according to claim 12 , the method comprising:
(a) passing a composition comprising the mixture of enantiomers through a chromatography column comprising as a stationary phase a chiral porous material of formula [M(L) 1.5 (A)] + X − ; (b) contacting the composition comprising the mixture of enantiomers with a crystalline chiral porous material of formula [M(L) 1.5 (A)] + X − for a period sufficient for the composition to equilibrate; and (c) obtaining the crystal structure of the material obtained in step (b), thereby identifying an enantiomer.

Assignees

• Univ Nankai
• Univ Limerick

Inventors

• Shi Wei
• Cheng Peng
• Yan xiu-ping
• Yang Cheng-Xiong
• Zaworotko Michael J
• Zhang shi-yuan

Classifications

• C07C253/34

  Separation; Purification · CPC title

• C07C59/56

  containing halogen · CPC title

• B01J20/29 Primary

  Chiral phases · CPC title

• B01J20/226

  Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF] (preparation of metal complexes containing carboxylic acid moieties C07C51/418; MOF's per se C07F) · CPC title

• C07B57/00 Primary

  Separation of optically-active compounds · CPC title