Bioreachable chiral dopants for liquid crystal applications

Patent metadata

Field	Value
Publication number	US-11814563-B2
Application number	US-201917299777-A
Country	US
Kind code	B2
Filing date	Dec 6, 2019
Priority date	Dec 7, 2018
Publication date	Nov 14, 2023
Grant date	Nov 14, 2023

Abstract

The disclosure discusses chiral dopants for liquid-crystalline materials. Chiral dopants can be bioreachable compounds, i.e. compounds produced from microbes through fermentation. Chiral dopants can also include bioreachable materials that are further modified by chemical synthetic steps. Chiral dopants as discussed herein can include biomolecules such as glycyrrhetinic acid (1), S-naringenin (2), shikimic acid (3), alpha-phellandrene (4), betulin (5), malic acid (6), valencene (7), or nootkatone (8), and any stereoisomers or chemically modified derivatives thereof. The disclosure further shows optical properties of such compounds in a liquid-crystalline material.

First claim

What is claimed is:

1. A liquid-crystalline material comprising at least one chiral dopant selected from the group consisting of the structures

wherein R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, an aliphatic moiety, an aryl moiety, an arylalkylene moiety, an alkyl arylene moiety, an alkanoyl moiety, an arylalkanoyl moiety, or any halogenated derivative of the foregoing moieties, and
wherein Z is selected from C(H)R 5 , —CR 5 ═CR 5 —, O, S, or NRs, wherein R 5 is independently hydrogen, an aliphatic moiety, an aryl moiety, an arylalkylene moiety, an alkyl arylene moiety, an alkanoyl moiety, an arylalkanoyl moiety, or any halogenated derivative of the foregoing moieties, and
a nematic or a nematogenic substance.

2. The liquid-crystalline material according to claim 1 , wherein the at least one chiral dopant is present in an amount of at least 0.001 wt %, based on the weight of the liquid-crystalline material.

3. The liquid-crystalline material according to claim 1 , wherein the at least one chiral dopant is present in an amount of not greater than 20 wt %, based on the weight of the liquid-crystalline material.

4. The liquid-crystalline material according to claim 1 , further comprising at least one polymerizable mesogenic compound having at least one polymerizable functional group.

5. The liquid-crystalline material according to claim 4 , wherein the at least one polymerizable functional group includes an epoxy group, a vinyl group, an allyl group, an acrylate, a methacrylate, an isoprene group, an alpha-amino carboxylate, or any combination thereof.

6. The liquid-crystalline material according to claim 1 , wherein the nematic or the nematogenic substance is selected from azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl benzoates, cyclohexyl benzoates, phenyl esters of cyclohexanecarboxylic acid, cyclohexyl esters of cyclohexanecarboxylic acid, phenyl esters of cyclohexylbenzoic acid, cyclohexyl esters of cyclohexylbenzoic acid, phenyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl esters of benzoic acid, cyclohexylphenyl esters of cyclohexanecarboxylic acid, cyclohexylphenyl esters of cyclohexylcyclohexanecarboxylic acid, phenylcyclohexanes, cyclohexylbiphenyls, phenylcyclohexylcyclohexanes, cyclohexylcyclohexanes, cyclohexylcyclohexenes, cyclohexylcyclohexylcyclohexenes, 1,4-bis-cyclohexylbenzenes, 4,4′-bis-cyclohexylbiphenyls, phenylpyrimidines, cyclohexylpyrimidines, phenylpyridines, cyclohexylpyridines, phenylpyridazines, cyclohexylpyridazines, phenyldioxanes, cyclohexyldioxanes, phenyl-1,3-dithianes, cyclohexyl-1,3-dithianes, 1,2-diphenylethanes, 1,2-dicyclohexylethanes, 1-phenyl-2-cyclohexylethanes, 1-cyclohexyl-2-(4-phenylcyclohexyl) ethanes, 1-cyclohexyl-2-biphenylethanes, 1-phenyl-2-cyclohexylphenylethanes, halogenated stilbenes, benzyl phenyl ether, tolanes, substituted cinnamic acids, or any combination thereof.

Assignees

• Zymergen Inc
• Univ Kent State Ohio

Inventors

• Safir Adam
• Raja Shilpa Naresh
• Zoombelt Arjan
• Twieg Robert J
• Nepal Pawan
• Wedige-Fernando Ashani
• Palffy-Muhoray Peter

Classifications

• C09K19/588 Primary

  Heterocyclic compounds · CPC title

• C09K19/586 Primary

  Optically active dopants; chiral dopants · CPC title

• G02F1/13718

  based on a change of the texture state of a cholesteric liquid crystal · CPC title

• G02B5/20

  Filters (polarising elements G02B5/30) · CPC title

• C09K19/02

  characterised by optical, electrical or physical properties of the components, in general · CPC title