Liquid crystal compounds having a chiral fluorinated terminal portion

Fluorine-containing, chiral liquid crystal compounds having smectic mesophases or latent smectic mesophases, the compounds comprising (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting said terminal portions; said alkylene or fluoroalkylene group of said chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between said chiral center of said chiral fluorochemical terminal portion and said central core.

Fluorine-containing, chiral liquid crystal compounds having smectic mesophases or latent smectic mesophases, the compounds comprising (a) a chiral fluorochemical terminal portion represented by the formula --D--R*--D--R.sub.f, where R* is a cyclic or acyclic chiral moiety containing at least one chiral center; R.sub.f is perfluoroether; and each D is independently and non-directionally selected from the group consisting of a covalent bond, ##STR246## and combinations thereof, where one or more hydrogen atoms can optionally be replaced with fluorine, and where r and r' are independently integers of 0 to about 20, s is independently an integer of 1 to about 10 for each (C.sub.s H.sub.2s O), t is an integer of 1 to about 6, and p is an integer of 0 to about 4; with the proviso that there are at least 3 in-chain atoms between said central core and at least one said chiral center of R*; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting said terminal portions.

Chiral liquid crystal intermediate compounds represented by the following general formulas IV and VI: ##STR250## B".dbd.D--R.sub.f (VII) ##STR251## b and c are each independently zero or an integer of from 1 to 3; B is non-directionally selected from the group consisting of a covalent bond, --C(.dbd.O)--O--, --C(.dbd.O)--S--, --C(.dbd.O)--Se--, --C(.dbd.O)--Te--, --(CH.sub.2 CH.sub.2).sub.k -- where k is 1 to 4, --CH.dbd.CH--, --C.tbd.C--, --CH.dbd.N--, --CH.sub.2 --O--, --C(.dbd.O)--, and --O--; each Y and Z are independently selected from the group consisting of --H, --Cl, --F, --Br, --I, --OH, --OCH.sub.3, --CH.sub.3, --CF.sub.3, --OCF.sub.3, --CN, and --NO.sub.2 ; each m and n are independently zero or an integer of 1 to 4; each D is non-directionally and independently selected from the group consisting of a covalent bond, ##STR252## where one or more hydrogen atoms can optionally be replaced with fluorine, and where r and r' are independently integers of 0 to about 20, s is independently an integer of 1 to about 10 for each (C.sub.s H.sub.2s O), t is an integer of 1 to about 6, and p is an integer of 0 to about 4; R* is a cyclic or acyclic chiral moiety containing at least one chiral center and selected from the group consisting of ##STR253## where each R' is independently selected from the group consisting of --Cl, --F, --CF.sub.3, --NO.sub.2, --CN, --H, --C.sub.q H.sub.2q+1, --O--(O.dbd.)C--C.sub.q H.sub.2q+1, --C(.dbd.O)--O--C.sub.q H.sub.2q+1, --Br, --OH, and --OC.sub.q H.sub.2q+1 ; q' is independently an integer of 1 to about 20 for each (C.sub.q H.sub.2q' --O); q is an integer of 1 to about 20; w is an integer of 0 to about 10; v is an integer of 0 to about 3; each v' is independently an integer of 0 to about 3; q is an integer of 1 to about 3; each D is independently and non-directionally selected from the group set forth for D above, with the proviso that the ring containing D has from about 3 to about 10 ring atoms; each W is independently selected from the group consisting of N, CR', and SiR'; and with the proviso that R* is chiral; R.sub.f is fluoroalkyl, perfluoroalkyl, fluoroether, or perfluoroether; with the proviso that there are at least 3 in-chain atoms between said central core structure .paren open-st.P.paren close-st..sub.2 -- or ##STR254## and A" and B" are selected from the group consisting of --H, --Cl, --Br, --I, --OH, --COOH, --CH(CH.sub.2 OH).sub.2, --SH, --SeH, --TeH, --NH.sub.2, --COCl, --CHO, --C.tbd.CH, dialkyl borane, --CH.dbd.CH.sub.2, --OSO.sub.2 R.sub.f'", --OSO.sub.2 CH.sub.3, --OSO.sub.2 -cyclo(C.sub.6 H.sub.4)--CH.sub.3, --CH.sub.2 COOH, --NH(C.dbd.O)OC.sub.q H.sub.2q+1, --NCO, and --CH(C(O)O--C.sub.q H.sub.2q+1).sub.2, where R.sub.f '" is perfluoroalkyl group having from 1 to about 10 carbon atoms and q is an integer of 0 to about 20.