Method for enantiomeric enrichment

Patent metadata

Field	Value
Publication number	US-11420909-B2
Application number	US-201917259962-A
Country	US
Kind code	B2
Filing date	Jul 17, 2019
Priority date	Jul 18, 2018
Publication date	Aug 23, 2022
Grant date	Aug 23, 2022

Abstract

According to the present invention there is provided a method for enantiomeric enrichment of a mixture of two enantiomers of a chiral compound, the method comprises the application of the mixture of two enantiomers of a chiral compound onto a surface of a support material for producing a coated support, the determination a first value of an optical activity (OA0) of the coated support, the irradiation of the coated support with a light beam having an intensity at least higher than a desorption threshold of one of the enantiomers from the coated support, wherein, if the support material is achiral, the light beam is circularly polarized and, if the support material is chiral, the light beam is unpolarized, linearly polarized or circularly polarized, and the determination of a second value of the optical activity (OAe) of the coated support after said irradiation, wherein the second value of the optical activity (OAe) differs from the first value of the optical activity (OA0).

First claim

The invention claimed is:

1. A method for enantiomeric enrichment of a mixture of two enantiomers of a chiral compound, the method comprising:
applying the mixture of two enantiomers of a chiral compound onto a surface of a support material for producing a coated support;
determining a first value of an optical activity of the coated support;
irradiating the coated support with a light beam having an intensity at least higher than a desorption threshold of one of the enantiomers from the coated support, wherein, if the support material is achiral, the light beam is circularly polarized and, if the support material is chiral, the light beam is unpolarized, linearly polarized or circularly polarized; and
determining a second value of the optical activity of the coated support after said irradiating, the second value of the optical activity differing from the first value of the optical activity.

2. The method according to claim 1 , further comprising repeating said irradiating and said determining in order to obtain a final value of the optical activity of the coated support, which value corresponds to a given value of the optical activity.

3. The method according to claim 2 , wherein the light beam has a wavelength that matches resonantly with an optical transition of the chiral compound, either by a single photon or by multiple photons.

4. The method according to claim 1 , wherein said irradiating has a duration between 0.2 ns and 1000 s.

5. The method according to claim 1 , wherein said irradiating comprises irradiating the coated support using by one of a light emitting diode, a pulsed laser or a continuous wave laser.

6. The method according to claim 1 , wherein said determining includes determining the value of the optical activity by circular dichroism.

7. The method according to claim 1 , wherein said applying includes an application of the enantiomeric mixture of two enantiomers by molecular evaporating.

8. The method according to claim 1 , wherein the chiral support material belongs to the group of high Miller index surfaces of metals.

9. The method according to claim 1 , wherein the achiral support material belongs to the group of amorphous solids of low Miller index surfaces of a metal.

10. The method according to claim 1 , wherein the mixture of the two enantiomers is provided in powder.

11. The method according to claim 1 , wherein the light beam has a wavelength that matches resonantly with an optical transition of the chiral compound by multiple photons.

12. The method according to claim 1 , wherein said irradiating comprises irradiating the coated support using a pulsed laser or a continuous wave laser.

13. The method according to claim 1 , wherein said irradiating comprises irradiating the coated support using a continuous wave laser.

14. The method according to claim 1 , wherein said determining includes determining the value of the optical activity by optical rotation dispersion.

15. The method according to claim 1 , wherein said determining includes determining the value of the optical activity by second harmonic generation circular dichroism.

16. The method according to claim 1 , wherein said determining includes determining the value of the optical activity by second harmonic generation optical rotation.

17. The method according to claim 1 , wherein said applying includes an application of the enantiomeric mixture of two enantiomers by spin coating.

18. The method according to claim 1 , wherein said applying includes an application of the enantiomeric mixture of two enantiomers by dip coating.

19. The method according to claim 1 , wherein said applying includes an application of the enantiomeric mixture of two enantiomers by drop casting.

20. The method according to claim 1 , wherein the mixture of the two enantiomers is provided in liquid form.

Assignees

• Univ Muenchen Tech

Inventors

• Kartouzian Aras
• Heiz Ulrich
• Mortaheb Farinaz
• Oberhofer Katrin
• Riemensberger Johann
• Iglev Hristo
• Kienberger Reinhard

Classifications

• C07B57/00 Primary

  Separation of optically-active compounds · CPC title

• C07C37/685

  Processes comprising at least two steps in series · CPC title

• G01N21/19

  Dichroism · CPC title