Liquid crystal quantitative analysis method for optically active compounds

• US 4,011,046 A
• Filed: 11/12/1975
• Issued: 03/08/1977
• Est. Priority Date: 11/12/1975
• Status: Expired due to Term

• Current Assignee: Temple University
• Original Assignee: Temple University
• Inventors: Labes, Mortimer M.
• Primary Examiner(s): Serwin, R.E.
• Application Number:
  US05/631,100
• Time in Patent Office: 482 Days
• Field of Search: 23/230 R, 23/230 B, 23/230 LC
• US Class Current: 436/92
• CPC Class Codes: G01N 21/45 using interferometric methods; using Schlieren methods
• CPC Class Codes: G02F 1/0063 Optical properties, e.g. absorption, reflection or birefringence materials for non-linear optics G02F1/355
• CPC Class Codes: Y10T 436/141111 Diverse hetero atoms in same or different rings [e.g., alkaloids, opiates, etc.]
• CPC Class Codes: Y10T 436/173845 Amine and quaternary ammonium

Abstract

Using a standardized cell containing a thin layer of an aligned nematic liquid crystalline material, a relationship is determined between concentration of an optically active solute material in the liquid crystal layer and line spacing in a pattern produced by differential light refraction, upon the injection of different amounts of the optically active compound. Subsequently, quantitative analysis of a sample containing the optically active compound is accomplished by injecting a known amount of the sample into a second identical standardized cell, observing the line spacing of refracted light in the second cell and comparing it to the relationship determined in the first cell. Optically active compounds analyzable in this manner include steroids and cholesteryl esters. A preferred nematic liquid crystalline material is n-p-methoxybenzylidene-p-n-butylaniline. A specific system described consists of cholesteryl-2-methyl valerate in homeotropically aligned n-p-methoxybenzylidene-p-n butylaniline with a layer thickness in the cell of 12.7 microns.

Claims

1. Method for quantitatively analyzing a sample, for a specific optically active compound contained therein, by first determining the relationship between line spacing of differentially refracted light and concentration of said optically active compound in a nematic liquid crystalline material oriented in a first standardized cell consisting of a thin layer of said liquid crystalline material disposed between transparent cell face members, and subsequently injecting a preselected amount of said sample into the nematic liquid crystalline layer of a second standardized cell identical with said first cell, observing the line spacing of refracted light in said second cell and comparing it to the relationship determined in said first cell and, on the basis of said comparison, determining the quantity of said optically active compound in said second cell.

2. Method, as recited in claim 1, wherein the thickness of said nematic liquid crystalline layer is from 6 to 150 microns and the side dimensions of the aligned liquid crystalline layer area is from 0.2 to 3 centimeters.

3. Method, as recited in claim 1, wherein said nematic liquid crystalline material is a nematogenic Schiff base, such as n-p-methoxybenzylidene-p-n-butyl aniline.

4. Method, as recited in claim 1, wherein said nematic liquid crystalline material is a compensated mixture of cholesteric liquid crystals.

5. Method, as recited in claim 1, wherein said nematic liquid crystalline material is a mixture of cholesteryl chloride and cholesteryl myristate, compensated at 43°

C.

6. Method, as recited in claim 1, wherein said nematic liquid crystalline material is a substituted azoxybenzene nematogen.

7. Method, as recited in claim 1, wherein said nematic liquid crystalline material is p-methoxy-p'"'"'-n-butyl azoxybenzene.

8. Method, as recited in claim 1, wherein said nematic liquid crystalline material is substituted phenyl-4-benzoyl oxy benzoate.

9. Method, as recited in claim 1, wherein said nematic liquid crystalline material is substituted benzoyloxy benzoate.

10. Method, as recited in claim 1, wherein said nematic liquid crystalline material is a substituted biphenyl.

11. Method, as recited in claim 1, wherein said nematic liquid crystalline material is p-n-heptyl-p'"'"' cyanobiphenyl.

12. Method, as recited in claim 1, wherein said liquid crystalline material is a mixture of one or more nematogenic materials.

13. Method, as recited in claim 1, wherein said nematic liquid crystalline material is homeotropically aligned.

14. Method, as recited in claim 1, wherein said nematic liquid crystalline material is homogeneously aligned.

15. Method, as recited in claim 1, wherein said optically active compound is a steroidal compound.

16. Method, as recited in claim 1, wherein said optically active compound is a cholesteryl derivative.

17. Method, as recited in claim 1, wherein said optically active compound is cholesteryl-2-methyl valerate.

18. Method, as recited in claim 1, wherein said optically active compound is an optically active amphetamine.

19. Method, as recited in claim 1, wherein said optically active compound is optically active dextroamphetamine.

20. Method, as recited in claim 1, wherein said optically active compound is an optically active organic acid.

21. Method, as recited in claim 1, wherein said optically active compound is optically active tartaric acid.

22. Method, as recited in claim 1, wherein said optically active compound is an alkaloid compound.

23. Method, as recited in claim 1, wherein said optically active compound is a morphine alkaloid.

24. Method, as recited in claim 1, wherein said optically active compound is an indole alkaloid.

25. Method, as recited in claim 1, wherein said optically active compound is a cinchona alkaloid.

26. Method, as recited in claim 1, wherein said optically active compound is an ergot alkaloid.

27. Method, as recited in claim 1, wherein said optically active compound is morphine.

28. Method, as recited in claim 1, wherein said optically active compound is codeine.

29. Method, as recited in claim 1, wherein said optically active compound is an optically active terpenoid alcohol.

30. Method, as recited in claim 1, wherein said optically active compounds is a chiral nematic liquid crystal.

31. Method, as recited in claim 1, wherein said optically active compound is an optically active sugar compound or sugar derivative.