Liquid crystal compounds having a chiral fluorinated terminal portion

The compounds of claim 4 wherein said R* is selected from the group consisting of --O--((C.sub.q' H.sub.2q'-v' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q-v --(R').sub.v --, --((C.sub.q' H.sub.2q'-v' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q-v --(R').sub.v --, --C(.dbd.O)--O--C.sub.q H.sub.2q-v --(R').sub.v --, --O--(O.dbd.)C--C.sub.q H.sub.2q-v --(R').sub.v --, ##STR94## where each R' is independently selected from the group consisting of --Cl, --F, --CF.sub.3, --NO2, --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 6;
• each v' is independently an integer of 0 to about 6;
• g is an integer of 1 to about 3;
• each D is independently and non-directionally selected from the group set forth for D in claim 5, 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.

Fluorine-containing, chiral liquid crystal compounds having smectic mesophases or latent smectic mesophases, the compounds comprising (a) a chiral fluorochemical terminal portion containing at least one methylene group and at least one perfluoroether group, said chiral fluorochemical terminal portion being represented by the formula --D--R*--D--(O).sub.x --CH.sub.2 --D'--R.sub.f, where R* is a cyclic or acyclic chiral moiety;

• x is an integer of 0 or 1:
• R.sub.f is perfluoroether;
• and D' and each D are independently and non-directionally selected from the group consisting of a covalent bond, --C(.dbd.O)--O--C.sub.r H.sub.2r --, --O--C.sub.r H.sub.2r --, --O.paren open-st.C.sub.s H.sub.2s O.paren close-st..sub.t C.sub.r' H.sub.2r' --, --C.sub.r H.sub.2r --, .paren open-st.C.sub.s H.sub.2s O.paren close-st..sub.t C.sub.r' H.sub.2r' --, --OSO.sub.2 --, --SO.sub.2 --, --SO.sub.2 --C.sub.r H.sub.2r --, ##STR95## --S--, --N(C.sub.p H.sub.2p+1)--, and combination thereof, where and 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;
• (b) a saturated, chiral or achiral, hydrocarbon terminal portion;
• and (c) a central core connecting said terminal portions.

A process for preparing fluorine-containing, chiral liquid crystal compounds comprising the steps of (a) mixing at least one compound represented by the formula ##STR96## with at least one compound represented by the formula ##STR97## or mixing at least one compound represented by the formula ##STR98## with at least one compound represented by the formula ##STR99## or mixing at least one compound represented by the formula ##STR100## with at least one compound represented by the formula ##STR101## where M, N, and P are each independently selected from the group consisting of ##STR102## a, b, and c are each independently zero or an integer of from 1 to 3, with the proviso that the sum of a+b+c be at least 1:

• each A and B are non-directionally and independently 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 X, 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 l, m, and n are independently zero or an integer of 1 to 4;
• D is non-directionally selected from the group consisting of a covalent bond,
• --C(.dbd.O)--O--C.sub.r H.sub.2r --, --O--C.sub.r H.sub.2r --, --O--(O.dbd.)C--C.sub.r H.sub.2r --, --C.tbd.C--, --CH.dbd.CH--, --C(.dbd.O)--, --O.paren open-st.C.sub.2 H.sub.2s O.paren close-st..sub.t C.sub.r' H.sub.2r' --, --C.sub.r H.sub.2r --, .paren open-st.C.sub.s H.sub.2s O.paren close-st..sub.t C.sub.r' H.sub.2r' --, --O--, --S--, --OSO.sub.2 --, --SO.sub.2 --, --SO.sub.2 --C.sub.r H.sub.2r --, ##STR103## --N(C.sub.p H.sub.2p+1)--, ##STR104## --CH.dbd.N--, and combinations thereof, where r and r' are independently integer 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 selected from the group consisting of --O--(C.sub.q' H.sub.2q'-v' --(R').sub.v')--O).sub.x --C.sub.q H.sub.2q+1-v --(R').sub.v, --((C.sub.q' H.sub.2q'-y' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q+1-v --(R').sub.v, --C(.dbd.O)--O--C.sub.q H.sub.2q+1-v --(R').sub.v, --O--(O.dbd.)C--C.sub.q H.sub.2q+1-v --(R').sub.v, ##STR105## --CR'H--(D).sub.g--CR'H--C.sub.q H.sub.2q+1-v --(R').sub.v, where each R' is independently selected from the group consisting of --Cl, --F, --CF.sub.3, --NO.sub.2, --CH, --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 6:
• each v' is independently an integer of 0 to about 6;
• g 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 R is chiral or achiral;
• and R.sub.f ' is --R*--D--(O).sub.x --CH.sub.2 --D'--R.sub.f, where R* is a cyclic or acyclic chiral moiety:
• D and D' are each independently and non-directionally selected from the group set forth for D above;
• x is an integer of 0 or 1:
• and R.sub.f is fluoroalkyl, perfluoroalkyl, fluoroether, or perfluoroether;
• x is an integer of 0 or 1, with the proviso that x is 1 and a+b is at least 1 when compound III is mixed with compound VII;
• and each A', A", B', and B" are independently 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, --OSO.sub.2 R.sub.f '", --OSO.sub.2 CH.sub.3, --NH(C.dbd.O)OC.sub.q H.sub.2q+1, --NCO, --OSO.sub.2 -cyclo(C.sub.6 H.sub.4)--CH.sub.3, --CH.sub.2 COOH, and --CH(C(O)O--C.sub.q H.sub.2q+1).sub.2, where R.sub.f '" is a perfluoroalkyl group having from 1 to about 10 carbon atoms and q is an integer of 0 to about 20, and with the proviso that (R*).sub.x --A' can enter into an addition or condensation reaction with A" and that (R*).sub.x --B' can enter into an addition or condensation reaction with B";
• and (b) allowing compounds III and IV, compounds V and VI, or compounds III and VII to react.

Chiral liquid crystal intermediate compounds represented by the following general formulas IV, VI, and VII:

• ##STR106## where N and P are each independently selected from the group consisting of ##STR107## 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;
• D is non-directionally selected from the group consisting of a covalent bond, --C(.dbd.O)--O--C.sub.r H.sub.2r --, --O--C.sub.r H.sub.2r --, --O--(O.dbd.)C--C.sub.r H.sub.2r --, --C.tbd.C--, --CH.dbd.CH--, --C(.dbd.O)--, --O.paren open-st.C.sub.s H.sub.2s O.paren close-st..sub.t C.sub.r' H.sub.2r' --, --C.sub.r H.sub.2r --, .paren open-st.C.sub.s H.sub.2s O.paren close-st..sub.t C.sub.r' H.sub.2r' --, --O--, --S--, --OSO.sub.2 --, --SO.sub.2 --, --SO.sub.2 --C.sub.r H.sub.2r --, ##STR108## --N(C.sub.p H.sub.2p+1)--, ##STR109## --CH.dbd.N--, and combinations thereof, 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:
• and
• R.sub.f ' is --R*--D--(O).sub.x --CH.sub.2 --D'--R.sub.f, where R* is a cyclic or acyclic chiral moiety:
• D and D' are each independently and non-directionally selected from the group set forth for D above;
• x is an integer of 0 or 1;
• and R.sub.f is fluoroalkyl, perfluoroalkyl, fluoroether, or perfluoroether;
• 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, --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 a perfluoroalkyl group having from 1 to about 10 carbon atoms and q is an integer of 0 to about 20;
• with the proviso that, for compound VII, B'" is --CH(C(O)O--C.sub.q H.sub.2q+1).sub.2.