Synthesis of optically active 4,4,4-trifluoro-3-{4-(4-methoxyphenyl)phenyl}butanoic acid and its application to chiral dopant for nematic liquid crystals

• Published in: Journal of fluorine chemistry Vol. 127; no. 4; pp. 620 - 626
• Main Authors: Tojo, Kenta, Aoki, Yoshio, Yasutake, Mikio, Hirose, Takuji
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.05.2006; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chiral dopant; Helical twisting power; Nematic liquid crystals; Physical Sciences; Science & Technology; Trifluoromethyl asymmetric frame; Chiral dopant; Trifluoromethyl asymmetric frame; Nematic liquid crystals; Helical twisting power; chiral dopant; nematic liquid crystals; trifluoromethyl asymmetric frame; helical twisting power
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2005.11.005

We synthesized an optically active 4,4,4-trifluoro-3-{4-(4-methoxyphenyl)phenyl}butanoic acid ( 5 *). New chiral dopants for nematic liquid crystals were derived from ( R)-(−)- 5 *, and their helical twisting power (HTP) values were measured. The chiral dopant, ( R)-(+)-4,4,4-trifluoro-1-(4-hexyloxyphenyl)-3-{4-(4-methoxyphenyl)phenyl}-1-butanone showed the largest HTP value. ▪ We synthesized an optically active 4,4,4-trifluoro-3-{4-(4-methoxyphenyl)phenyl}butanoic acid ( 5 *). New chiral dopants for nematic liquid crystals were derived from ( R)-(−)- 5 *, and their helical twisting power (HTP) values were measured. Their HTP values were largely influenced by the linkage between the asymmetric frame and the core moiety. The chiral dopant, ( R)-(+)-4,4,4-trifluoro-1-(4-hexyloxyphenyl)-3-{4-(4-methoxyphenyl)phenyl}-1-butanone (( R)-(+)- 7 *) showed the largest HTP value (−21.7 μm −1).