Polar nematic compounds
Polar nematic compounds, one example of which has the following structure: is a caged boron structure, where the sphere of the caged boron structure is C and each non-sphere vertex of the caged boron structure is B—H. R is H, an alkyl, a cycloalkyl, a bicycloalkyl, an alkenyl, a cycloalkenyl, a bicycloalkenyl, an alkynyl, an acyl, an aryl, an alkylaryl, a halogen, a cyano group, or an isothiocyanoto group, or R is a group that forms an ether, a ketone, an ester, a thioester, a sulfide, or a sulfone. X is COOR′ or COSR′. R′ is H, an alkyl, a cycloalkyl, a bicycloalkyl, an alkenyl, a cycloalkenyl, a bicycloalkenyl, an alkynyl, an aryl, a halogen, or a cyano group. The compounds may be used in liquid crystal displays (LCDs), and in television sets, laptop computers, computer monitors, hand-held communication devices, gaming devices, watches, cash registers, clocks, and calculators having liquid crystal displays.
1. A compound comprising the following structure:
wherein
is a caged boron structure where the sphere of the caged boron structure is C and each non-sphere vertex of the caged boron structure is B—H;
wherein R is H, an alkyl, a cycloalkyl, a bicycloalkyl, an alkenyl, a cycloalkenyl, a bicycloalkenyl, an alkynyl, an acyl, an aryl, an alkylaryl, a halogen, a cyano group, or an isothiocyanoto group, or where R is a group that forms an ether, a ketone, an ester, a thioester, a sulfide, or a sulfone;
wherein X is COOR′ or COSR′; and
wherein R′ is H, an alkyl, a cycloalkyl, a bicycloalkyl, an alkenyl, a cycloalkenyl, a bicycloalkenyl, an alkynyl, or an aryl.
2. The compound of claim 1 , wherein R is H, a C 2 -C 9 alkyl, a C 2 -C 9 alkenyl, or a C 2 -C 9 alkoxy.
3. The compound of claim 1 , wherein R is propyl or heptyl.
4. The compound of claim 1 , wherein X is COOR′.
5. The compound of claim 1 , wherein R′ is H, a C 2 -C 9 alkyl, a C 2 -C 9 alkenyl, a C 6 -C 8 cycloalkyl, or an aryl.
6. The compound of claim 1 , wherein R′ is
7. The compound of claim 1 , wherein the compound is:
8. A method of making the compound of claim 1 , comprising:
heating a mixture comprising
and a thiocarbonyl to form an intermediate; and
reacting the intermediate under hydrolytic conditions with RCH(CH 2 CH 2 X′) 2 , where X′ is a halogen.
9. A method of making the compound of claim 1 , comprising heating a mixture comprising
10. A mixture comprising the compound of claim 1 and a nematic host.
11. A liquid crystal display comprising the compound of claim 1 .
12. A television set, a laptop computer, a computer monitor, a hand-held communication device, a gaming device, a watch, a cash register, a clock, or a calculator comprising the liquid crystal display of claim 11 .