Chiral Liquid Crystals
129
2.5), 275 (C11H23O–C6H4–CO+, 100), 121 (HO–C6H4–CO+, 10.8). Elemental analysis:
calculated for C37H39O6F17, C 49.23, H 4.35%; found, C 48.98, H 4.19%.
Synthesis of Compound A12. M.p. 99.4◦C. IR (KBr, cm−1): 2922, 2853, 1733, 1734, 1607,
1
1512, 1468, and 1200. H NMR (300 MHz, CDCl3), δ (ppm) 0.88 (t, J = 6.6 Hz, 3H,
–CH2CH3), 1.23–1.85 (m, 20H, aliphatic hydrogens). 1.63 (d, J = 6.8 Hz, 3H, –CHCH3),
2.49 (tt, J1 = 18 Hz, J2 = 6.4 Hz 2H, –CH2Rf), 4.04 (t, J = 6.6 Hz, 2H, –CH2CH2Rf), 4.48
(t, J = 6.4 Hz, 2H, –OCH2), 4.77 (q, J = 6.8 Hz, 1H, –CHCH3), 6.90 (d, J = 9.2 Hz, 2H,
ArH), 6.95 (d, J = 8.8 Hz, 2H, ArH), 7.10 (d, J = 9.2 Hz, 2H, ArH), 8.11 (d, J = 8.8 Hz,
2H, ArH). 19F NMR (300 MHz, CDCl3): δ (ppm) −48.56 (t, J = 12.27 Hz, 2F), −45.98 (s,
2F), −45.16 (s, 2F), (−44.39 to −44.12) (m, 6F), −36.01 (m, 2F), −3.16 (t, J = 9.87 Hz,
3F). MS m/z (rel. int.): 916 (M++1), 425 (–C6H4–COO–C6H4–O–C+H–CH3, 1.1), 289
(C12H25–C6H4–CO+, 100), 121 (HO–C6H4–CO+, 14.2). Elemental analysis: calculated for
C38H41O6F17, C 49.79, H 4.51%; found, C 50.13, H 4.51%.
Synthesis of Compound B4. M.p. 113.0◦C. IR (KBr, cm−1): 2958, 2872, 1753, 1736, 1605,
1510, 1414, and 1198. 1H NMR (400 MHz, CDCl3, TMS): δ (ppm) 0.98 (t, J = 7.8 Hz, 3H,
–CH2CH3), 1.45–1.84 (m, 4H, aliphatic hydrogens), 1.62 (d, J = 6.8 Hz, 3H, –CHCH3),
2.47 (tt, J1 = 18 Hz, J2 = 6.4 Hz, 2H, –CH2Rf), 4.04 (t, J = 6.4 Hz, 2H, –CH2CH2Rf),
4.47 (t, J = 6.2 Hz, 2H, –OCH2), 4.76 (q, J = 6.5 Hz, 1H, –CHCH3), 6.90 (d, J = 9.2 Hz,
2H, ArH), 6.97 (d, J = 8.8 Hz, 2H, ArH), 7.11 (d, J = 8.8 Hz, 2H, ArH), 7.34 (d, J =
8.8 Hz, 2H, ArH), 8.13 (d, J = 8.8 Hz, 2H, ArH), 8.24 (d, J = 8.8 Hz, 2H, ArH). 19F
NMR (400 MHz, CDCl3): δ (ppm) −48.28 (t, J = 17.6 Hz, 2F), −45.70 (s, 2F), −44.83 (s,
2F), (−43.81–−44.12) (m, 6F), −35.71 (m, 2F), −2.91 (t, J = 9.87 Hz, 3F). MS m/z (rel.
int.): 924 (M++1),297 (C4H9O–C6H4–COO–C6H4–CO+, 20), 177 (C4H9O–C6H4–CO+,
100), 121 (HO–C6H4-CO+,15). Elemental analysis: calculated for C37H29O8F17, C 48.06,
H 3.16%; found, C 47.30, H 3.30%.
Synthesis of Compound B5. M.p. 112.5◦C. IR (KBr, cm−1), 2937, 2871, 1753, 1736, 1606,
1511, 1415, and 1199. 1H NMR (400 MHz, CDCl3, TMS): δ (ppm) 0.93 (t, J = 6.8 Hz, 3H,
–CH2CH3), 1.34–1.87 (m, 6H, aliphatic hydrogens). 1.62 (d, J = 6.8 Hz, 3H, –CHCH3),
2.47 (tt, J1 = 19.8 Hz, J2 = 6.8 Hz, 2H, –CH2Rf), 4.04 (t, J = 6.4 Hz, 2H, –CH2CH2Rf),
4.47 (t, J = 6.4 Hz, 2H, –OCH2), 4.76 (q, J = 6.6 Hz, 1H, –CHCH3), 6.90 (d, J = 6.8 Hz,
2H, ArH), 6.97 (d, J = 8.0 Hz, 2H, ArH), 7.11 (d, J = 8.8 Hz, 2H, ArH), 7.34 (d, J =
8.4 Hz, 2H, ArH), 8.13 (d, J = 8.0 Hz, 2H, ArH), 8.24 (d, J = 8.0 Hz, 2H, ArH). 19F NMR
(400 MHz, CDCl3): δ (ppm) −48.28 (t, J = 17.6 Hz, 2F), −45.70 (s, 2F), −44.83 (s, 2F),
(−43.81 to −44.12) (m, 6F), −35.71 (m, 2F), −2.91 (t, J = 9.87 Hz, 3F). MS m/z (rel.
int.): 938 (M++1), 311 (C5H11O–C6H4–COO–C6H4–CO+, 16), 191 (C5H11O–C6H4–CO+,
100), 121 (HO–C6H4–CO+, 20). Elemental analysis: calculated for C38H31O8F17, C 48.63,
H 3.33%; found, C 48.73, H 4.57%.
Synthesis of Compound B6. M.p. 113.2◦C. IR (KBr, cm−1), 2938, 2872, 1752, 1736, 1606,
1511, 1416, and 1199. 1H NMR (400 MHz, CDCl3, TMS): δ (ppm) 0.90 (t, J = 6.8 Hz, 3H,
–CH2CH3), 1.26–1.86 (m, 8H, aliphatic hydrogens). 1.62 (d, J = 6.8 Hz, 3H, –CHCH3),
2.47 (tt, J1 = 18.2 Hz, J2 = 6.0 Hz, 2H, –CH2Rf), 4.04 (t, J = 6.6 Hz, 2H, –CH2CH2Rf),
4.47 (t, J = 6.2 Hz, 2H, –OCH2), 4.76 (q, J = 6.5 Hz, 1H, –CHCH3), 6.90 (d, J = 8.8 Hz,
2H, ArH), 6.97 (d, J = 8.8 Hz, 2H, ArH), 7.11 (d, J = 8.8 Hz, 2H, ArH), 7.34 (d, J =
8.8 Hz, 2H, ArH), 8.13 (d, J = 8.8 Hz, 2H, ArH), 8.24 (d, J = 8.8 Hz, 2H, ArH). 19F NMR
(400 MHz, CDCl3): δ (ppm) −48.28 (t, J = 17.6 Hz, 2F), −45.70 (s, 2F), −44.83 (s, 2F),