Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units

Abstract

The subject application discloses a chiral nonracemic composition of the general formula: R.sub.1 --Ar--O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O--R.sub.2 wherein R 1 is an achiral tail of two to sixteen carbons; Ar is an achiral FLC core of at least two rings; * denotes a chiral carbon; X and Y are halogens; and R 2 is one to ten carbon atoms. The --O--CH 2 --C*HX--C*HY--CH 2 --O-- segment comprises the chiral proximal segment of the chiral tail; the proximal segment is selected from the enantiomers 2R,3R-dihalo and 2S,3S-dihalo. R 2 is the distal segment of the chiral tail.

We claim: 
     
       1. A chiral nonracemic compound of the formula:   R.sub.1 --AR--O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O--R.sub.2     wherein   * denotes a chiral carbon,   X and Y are halogens selected from the group of chlorine and fluorine, the .[.--O--CH 2  --C*HX--C--HY--CH 2  --O--.]. .Iadd.--O--CH 2  --C*HX--C*HY--CH 2  --O-- .Iaddend.segment comprises the chiral proximal segment of the chiral tails, said proximal segment being selected from the enantiomers 2R,3R-dihalo and 2S,3S-dihalo,   R 1  is an achiral alkyl, alkyl sulfide, alkyl ether, alkenyl, alkenyl sulfide, alkenyl ether, alkoxy, alkoxy sulfide, or alkoxy ether group of two to sixteen carbons,   Ar is an achiral FLC core selected from the group consisting of phenylbenzoates, phenylpyrimidines, biphenyls, phenylpyridines, biphenylbenzoates, diphenylpyrimidines, diphenylpyridines, terphenyls, phenyldiazenes, diphenyldiazenes, and diphenylthiadiazoles, and the chiral proximal segment and R 1  para-substituted with respect to each other on outer rings of said core, and R 2  is a distal segment of the chiral tail comprising one to ten carbon atoms and is selected from the group consisting of alkdehyde, alkyl acyl, alkyl, alkenyl, alkenyl acyl, alkyl halide, alkenyl halide, alkyl epoxide, and alkenyl epoxide.   
     
     
       2. The compound of claim 1, wherein R 1  comprises five to sixteen carbons. 
     
     
       3. The compounds of claim 4, wherein R 1  comprises eight carbons. 
     
     
       4. The compound of claim 1, wherein R 1  is selected from the group of straight-chain or branched. 
     
     
       5. The compound of claim 1, wherein R 2  comprises three carbons. 
     
     
       6. The compound of claim 1, wherein R 2  is selected from the group of straight-chain and branched. 
     
     
       7. The compound of claim 1, wherein R 2  comprises a chiral carbon. 
     
     
       8. The compound of claim 1, wherein R 2  is an alkyl halide consisting of two halogens. 
     
     
       9. The compound of claim 1, wherein said alkyl halides comprise fluorine or chlorine. 
     
     
       10. The compound of claim 1, wherein said composition is selected from the group consisting of .[.4'-[(2R,3R-difluoro-4-formyl)-butyloxy]phenyl-4-hexylpyrimidine.]. .Iadd.2-4'-(2R,3R-difluoro-4-formyloxybutyloxy)phenyl]-5-hexylpyrimidine .Iaddend.(X); .[.4'-[(2R,3R-difluoro-4-acetyl)butyloxy]phenyl-4-hexylpyrimidine.]. .Iadd.2-[4'-(2R,3R-difluoro-4-acetoxybutyloxy)phenyl]-5-hexylpyrimidine .Iaddend.(XI); .[.4'-[(2R,3R-difluoro-4-acetyl)butyloxy]phenyl-4-heptylpyrimidine.]. .Iadd.2-[4'-(2R,3R-difluoro-4-acetoxybutyloxy)phenyl]-5-heptylpyrimidine .Iaddend.(XII); .[.4'-[(2R,3R-difluoro-4-propanoate)butyloxy]phenyl-4-hexylpyrimidine.]. .Iadd.2-[4'-(2R,3R-difluoro-4-propanoatebutyloxy)phenyl]-5-hexylpyrimidine .Iaddend.(XIII); .[.4'-[(2R,3R-difluoro-4-butanoate)-butyloxy]phenyl-4-hexylpyrimidine.]. .Iadd.2-[4'-(2R,3R-difluoro-4-butanoatebutyloxy)phenyl]-5-hexylpyrimidine .Iaddend.(XIV); .[.4'-[(2R,3R-difluoro-4-pentanoate)butyloxy]phenyl-4-heptylpyrimidine.]. .Iadd.2-[4'-(2R,3R-difluoro-4-pentanoatebutyloxy)phenyl]-5-heptylpyrimidine .Iaddend.(XV); .[.4'-[2R,3R-difluoro-4-(4-pentanoate)-butyloxy]phenyl-4-hexylpyrimidine.]. .Iadd.2-{4'-[2R,3R-difluoro-4-(pent-4-enoate)butyloxy]phenyl}-5-hexylpyrimidine .Iaddend.(XVI); .[.4'-[2R,3R-difluoro-4-methoxy)butyloxy]-phenyl-4-heptylpyrimidine.]. .Iadd.2-[4'-(2R,3R-difluoro-4-methoxybutyloxy)phenyl]-5-heptylpyrimidine .Iaddend.(XVII); .[.4'-[(2R,3R-difluoro-4-butyloxy) butanoxy]phenyl-4-heptylpyrimidine.]. .Iadd.2-4'( 2R,3R-difluoro-4-butyloxybutyloxy)phenyl]-5-heptylpyrimidine .Iaddend.(XVIII); .[.4'-(2R,3R-difluoro-4-(4-pentenoxy)-butyloxy)phenyl-4-hexylpyrimidine.]. .Iadd.2-{4'-[2R,3R-difluoro-4-(pent-4-enoxy)butyloxy]phenyl}-5-hexylpyrimidine .Iaddend.(XIX); .[.4'-(2R,3R-difluoro-4-(1-methylheptyloxy)buty oxy)- phenyl-4-4-hexylpyrimidine.]. .Iadd.2-{4'-[2R,3R-difluoro-4-(R-1-methylheptyloxy)butyloxy]phenyl}-5-hexylpyrimidine .Iaddend.(XX); .[.4'-{[2R,3R-difluoro-4-(2R,3R-epoxy)hexyloxy]butyloxy}phenyl-4-hexylpy.]. .Iadd.2-{4'-[2R,3R-difluoro-4-(2R,3R-epoxyhexyloxy)butyloxy]phenyl}-5-hexylpyrimidine .Iaddend.(XXI); .[.4'-{[2R,3R-difluoro-4-(2S,3S-epoxy)hexyloxy]butyloxy}phenyl-4-hexylpyrimidine.]. .Iadd.2-{4'-[2R,3R-difluoro-4-(2S,3S-epoxyhexyloxy)butyloxy]phenyl}-5-hexylpyrimidine .Iaddend.(XXIII); .[.4'-[2R,3R-difluoro-4-(2S,3S-difluorohexyloxy)butyloxy]phenyl-4-hexylpyrimidine.]. .Iadd.2-{4'-[2R,3R-difluoro-4-(2S,3S-difluorohexyloxy)butyloxy]phenyl}-5-hexylpyrimidine .Iaddend.(XXIV); and .[.4'-[2R,3R-difluoro-4-(2R,3R-difluorohexyloxy)butyloxy]phenyl-4-hexylpyrimidine.]. .Iadd.2-{4'-[2R,3R-difluoro-4-(2R,3R-difluorohexyloxy)butyloxy]phenyl}-5-hexylpyrimidine .Iaddend.(XXII). 
     
     
       11. An FLC composition comprising the compound of claim 1.