Homochiral metal-organic framework with enantiopure pillar[5]arene active domains

Patent metadata

Field	Value
Publication number	US-9815764-B2
Application number	US-201514844708-A
Country	US
Kind code	B2
Filing date	Sep 3, 2015
Priority date	Sep 3, 2014
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

Homochiral metal organic framework (MOF) selected from a group consisting of (S p )-P5A-MOF-1 and (R p )-P5A-MOF-1 is provided. The homochiral MOFs are prepared from pure enantiomer struts of formula (I):

The homochiral MOFs are suitable for separation of enantiomers from racemic mixtures.

First claim

The invention claimed is:

1. A method of preparing a homochiral metal organic framework (MOF) consisting of (S p )-P5A-MOF-1, comprising:
preparing a mixture of (S p )-1 and Zn(NO 3 ) 2 in a solvent, wherein (S p )-1 is the S p -enantiomer structure of formula (I):

 and
heating the mixture at temperature of about 100° C. to form the homochiral metal organic framework (MOF) consisting of (S p )-P5A-MOF-1.

2. The method of claim 1 , wherein the solvent is anhydrous dimethylformamide.

3. A method of preparing a homochiral metal organic framework (MOF) consisting of (R p )-P5A-MOF-1, comprising:
preparing a mixture of (R p )-1 and Zn(NO 3 ) 2 in a solvent, wherein (R p )-1 is the R p -enantiomer structure of formula (I):

 and
heating the mixture at temperature of about 100° C. to form the homochiral metal organic framework (MOF) consisting of (R p )-P5A-MOF-1.

4. The method of claim 3 , wherein the solvent is anhydrous dimethylformamide.

5. A method of preparing a pure enantiomer structure of formula (I):

comprising:
preparing a mixture comprising an aqueous-base solution and a solvent comprising a pure enantiomer structure of formula (II):

heating the mixture at temperature of about 85° C. to form the pure enantiomer structure of formula (I).

6. The method of claim 5 , wherein the pure enantiomer structure of formula (I) consists of the (S p )-1 enantiomer and the pure enantiomer structure of formula (II) consists of the (SSS p )-4 enantiomer.

7. The method of claim 5 , wherein the pure enantiomer structure of formula (I) consists of the (R p )-1 enantiomer and the pure enantiomer structure of formula (II) consists of the (SSR p )-4 enantiomer.

8. The method of claim 5 , wherein the solvent is dimethoxyethane.

9. The method of claim 5 , wherein the aqueous-base solution is an aqueous sodium hydroxide.

Assignees

• Univ Northwestern
• King Abdulaziz City For Science And Tech (Kacst)

Inventors

• Stoddart James Fraser
• Strutt Nathan

Classifications

• C07C51/487

  by treatment giving rise to chemical modification (by chemisorption C07C51/47) · CPC title

• C07C2603/92

  with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes · CPC title

• C07F3/003

  without C-Metal linkages · CPC title

• C07C65/24 Primary

  polycyclic · CPC title

• C07B2200/07

  Optical isomers · CPC title