Beilstein J. Org. Chem. 2013, 9, 26–35.
ethyl acetate to obtain the pure product 1a as a yellow solid. CDCl3) δ 13.40 (1H, s, -OH), 8.59 (1H, s, –CH=N–), 8.08 (2H,
Yield = 0.30 g (58%); IR (KBr) νmax: 3186, 2951, 2864, 2221, d, J = 7.2 Hz, ArH), 7.73 (2H, d, J = 8.1 Hz, ArH), 7.67 (2H, d,
1741, 1604, 1512, 1490, 1384, 1344, 1288, 1220, 1192, 1163, J = 9.0 Hz, ArH), 7.64 (2H, d, J = 8.7 Hz, ArH), 7.55 (1H, d, J
1107, 744 cm−1; 1H NMR (400 MHz, CDCl3) δ 13.46 (s, 1H, = 7.6 Hz, ArH), 7.34 (2H, d, J = 8.4 Hz, ArH), 7.29 (2H,d, J =
-OH), 8.55 (s, 1H, -CH=N-), 7.86 (dd, J = 2.0, 7.6 Hz, 1H, 8.7 Hz, ArH), 6.49 (2H, d, J = 2.4, 8.4 Hz, ArH), 3.99 (2H, t, J
ArH), 7.75 (dd, J = 2.4 Hz, 8.8 Hz, 2H, ArH), 7.69 (dd, J = 2.0, = 6.4 Hz, -O-CH2-), 1.81–1.28 (12H, m, -(CH2)6-), 0.87 (3H, t,
8.8 Hz, 2H, ArH), 7.64 (dd, J = 2.4 Hz, 8.8 Hz, 2H, ArH), 7.46 -CH3); Anal. calcd for C35H34N2O4: C, 76.90; H, 6.27; found:
(d, J = 8.0 Hz, 1H, ArH), 7.42 (d, J = 8.0 Hz, 1H, ArH), 7.38 C, 76.28; H, 6.15.
(dd, J = 2.4, 8.0 Hz, 1H, ArH), 7.31 (dd, J = 2.0, 7.6 Hz, 2H,
ArH), 6.52 (dd, J = 2.4 Hz, 7.2 Hz, 2H, ArH), 4.02 (t, J = 4'-Cyano-[1,1'-biphenyl]-4-yl 3-((4-(hexyloxy)-2-hydroxy-
6.4 Hz, 2H, -OCH2-), 1.83–1.76 (m, 2H, -(CH2)-), 1.55–1.46 benzylidene)amino)-4-chlorobenzoate (1e): IR (KBr) νmax:
(m, 2H, -(CH2)-), 0.98 (t, 3H, -CH3); Anal. calcd for 3184, 2951, 2856, 2222, 1737, 1600, 1512, 1489, 1381, 1342,
C31H25ClN2O4: C, 70.92; H, 4.80; found: C, 70.61; H, 4.75. 1290, 1191, 1169, 1112, 746 cm−1; Anal. calcd for
C33H29ClN2O4: C, 71.67; H, 5.29; found: C, 71.14; H, 5.24.
For the synthesis of 1b–1f, the same experimental procedure as
described for the preparation of 1a (with appropriate chemicals 4'-Cyanobiphenyl-4-yl 3-((4-(hexadecyloxy)-2-hydroxyben-
as detailed in Scheme 2) was followed to obtain the yellow zylidene)amino)-4-chlorobenzoate (1f): IR (KBr) νmax: 3184,
solids. Yield of 1b = 0.32 g, 60%, yield of 1c = 0.30 g, 55% ; 2951, 2856, 2222, 1737, 1600, 1488, 1389, 1290, 1215, 1192,
yield of 1d = 0.31 g, 56%; yield of 1e = 0.33 g, 61%; yield of 1f 1170, 1112, 746 cm−1; Anal. calcd for C43H49ClN2O4: C,
= 0.45 g, 65%.
74.49; H, 7.12; found: C, 74.18; H, 7.02.
4'-Cyano-[1,1'-biphenyl]-4-yl 3-((4-(pentyloxy)-2-hydroxy- Acknowledgements
benzylidene)amino)-2-chlorobenzoate (1b): IR (KBr) νmax: The authors wish to thank Prof S. Kumar and Ms. K. N.
3186, 2951, 2864, 2218, 1739, 1602, 1512, 1487, 1392, 1344, Vasudha of the Raman Research Institute for DSC spectra.
1290, 1247, 1219, 1192, 1166, 1107, 748 cm−1; 1H NMR Financial assistance is provided to KU and GV (DST Inspire
(400 MHz, CDCl3) δ 13.46 (s, 1H, -OH), 8.55 (s, 1H, -CH=N-), fellowship) by the Department of Science and Technology and
7.86 (dd, J = 2.0, 7.2 Hz, 1H, ArH), 7.75 (d, J = 8.0 Hz, 2H, to GM (Maulana Azad fellowship) by the University Grants
ArH), 7.70 (d, J = 8.4 Hz, 2H, ArH), 7.67 (d, J = 8.8 Hz, 2H, Commission, New Delhi.
ArH), 7.47 (d, J = 8.0 Hz, 1H, ArH), 7.45 (dd, J = 2.8, 7.6 Hz,
References
1. Pelzl, G.; Weissflog, W. Mesophase Behaviour at the Borderline
1H, ArH), 7.42 (d, J = 8.0 Hz, 1H, ArH), 7.32 (d, J = 8.8 Hz,
2H, ArH), 6.53 (dd, J = 2.4, 8.8 Hz, 2H, ArH), 4.01 (t, 2H, J =
between Calamitic and ‘Banana-shaped’ Mesogens. In Thermotropic
6.4 Hz, -OCH2-), 1.84–1.77 (q, 2H, -(CH2)-), 1.48–1.34 (m, 4H,
liquid crystals; Ramamoorthy, A., Ed.; Springer: The Netherlands,
-(CH2)2-), 0.99 (t, J = 6.8 Hz, 3H, -CH3); Anal. calcd for:
C32H27ClN2O4: C, 71.30; H, 5.05; found: C, 71.18; H, 4.99.
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benzylidene)amino)-2-chlorobenzoate (1c): IR (KBr) νmax:
3184, 2951, 2856, 2222, 1737, 1600, 1512, 1487, 1386, 1342,
1290, 1215, 1192, 1170, 1112, 746 cm−1; 1H NMR (400 MHz,
CDCl3) δ 13.43 (s, 1H, -OH), 8.54 (s, 1H, -CH=N-), 7.85 (dd, J
= 2.0, 7.2 Hz, 1H, ArH), 7.74 (d, J = 8.4 Hz, 2H, ArH), 7.69 (d,
J = 8.8 Hz, 2H, ArH), 7.66 (d, J = 8.4 Hz, 2H, ArH), 7.45 (d, J
= 8.0 Hz, 1H, ArH), 7.33 (dd, J = 2.8, 8.0 Hz, 1H, ArH), 7.39
(d, J = 8.4 Hz, 1H, ArH), 7.31 (d, J = 8.8 Hz, 2H, ArH), 6.53
(dd, J = 2.0, 8.8 Hz, 2H, ArH), 4.02 (t, 2H, J = 6.4 Hz, -OCH2-
), 1.85–1.78 (q, 2H, -(CH2)-), 1.49–1.35 (m, 6H, -(CH2)3-),
0.92 (t, J = 6.8 Hz, 3H, -CH3); Anal. calcd for C33H29ClN2O4:
C, 71.67; H, 5.29; found: C, 71.21; H, 5.21.
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4'-Cyano-[1,1'-biphenyl]-4-yl 3-((4-(octyloxy)-2-hydroxy-
benzylidene)amino)benzoate, (1d): 1H NMR (400 MHz,
33