Achiral Bent-Core Liquid Crystalline Molecules
J. Chin. Chem. Soc., Vol. 57, No. 1, 2010 131
45.14; H 4.30.
3,4¢-Bis(4-nitrobenzoyloxy)-biphenyl (9a)
2-(Biphenyl-3-yloxy)-bis-tetrahydro-pyran (7a)
1
Yield 95%, as a yellowish solid, 1H NMR (300 MHz,
CDCl3) d: 7.26 (m, 1H), 7.34 (m, 2H), 7.47 (m, 1H), 7.55
(m, 2H), 7.70 (m, 2H), 8.40 (m, 8H); HRMS (ESI), m/z,
484.0906; Anal. Calc. for C26H16N2O8: C 64.47; H 3.33; N
5.78. Found: C 64.70; H 3.42; N 5.73.
Yield 78%, as a white solid, H NMR (300 MHz,
CDCl3) d: 1.62-1.81 (m, 6H), 1.93-2.13 (m, 6H), 3.62 (m,
2H), 4.02 (m, 2H), 5.51 (m, 2H), 7.03 (m, 1H), 7.12 (m,
2H), 7.15 (m, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 7.52 (m,
1H); HRMS (ESI), m/z, 354.1831; Anal. Calc. for
C22H26O4: C 74.55; H 7.39. Found: C 74.37; H 7.50.
2-(3¢-Fluoro-biphenyl-3-yloxy)-bis-tetrahydro-pyran
(7b)
3,4¢-Bis(4-nitrobenzoyloxy)-3¢-fluoro-biphenyl (9b)
Yield 90%, as a yellowish solid, 1H NMR (300 MHz,
CDCl3) d: 7.28 (m, 1H), 7.40 (m, 1H), 7.47 (m, 1H), 7.50-
7.6 (m, 3H), 7.75 (m, 1H), 8.43 (m, 8H); HRMS (ESI), m/z,
502.0812; Anal. Calc. for C26H15FN2O8: C 62.16; H 3.01;
N 5.58. Found: C 62.29; H 3.34; N 5.71.
1
Yield 69%, as a white solid, H NMR (300 MHz,
CDCl3) d: 1.55-1.77 (m, 6H), 1.87-2.08 (m, 6H), 3.55 (m,
2H), 3.95 (m, 2H), 5.45 (m, 2H), 6.95 (m, 1H), 7.01 (m,
1H), 7.12 (m, 1H), 7.15 (m, 1H), 7.25 (m, 1H), 7.35 (m,
1H), 7.45 (m, 1H), 7.55 (m, 1H); HRMS (ESI), m/z,
372.1737; Anal. Calc. for C22H25FO4: C 70.95; H 6.77.
Found: C 71.30; H 6.66.
3,4¢-Bis(4-nitrobenzoyloxy)-3¢-chloro-biphenyl (9c)
Yield 92%, as a yellowish solid, 1H NMR (300 MHz,
CDCl3) d: 7.29 (m, 1H), 7.49 (m, 1H), 7.51 (m, 1H), 7.60-
7.70 (m, 3H), 7.82 (m, 1H), 8.41 (m, 8H); HRMS (ESI),
m/z, 518.0517; Anal. Calc. for C26H15ClN2O8: C 60.19; H
2.91; N 5.40. Found: C 60.15; H 2.79; N 5.60.
2-(3¢-Chloro-biphenyl-3-yloxy)-bis-tetrahydro-pyran
(7c)
3,4¢-Bis(4-aminibenzoyloxy)-biphenyl (10a)
1
Yield 69%, as a colorless viscous liquid, H NMR
Yield 97%, as a yellow powder, IR (KBr) v/cm-1
3475, 3365, 3221, 3064, 2924, 2852, 2674, 1915, 1700,
1624, 1597, 1516, 1481, 1445, 1395, 1319, 1270, 1212,
1167, 1069, and 1010; 1H NMR (300 MHz, CDCl3) d: 6.21
(s, 4H), 6.42 (m, 4H), 7.18-7.30 (m, 3H), 7.49-7.60 (m,
3H), 7.73-7.83 (m, 6H); HRMS (ESI), m/z, 424.1423;
Anal. Calc. for C26H20N2O4: C 73.57; H 4.75; N 6.60.
Found: C 73.45; H 4.89; N 6.45.
(300 MHz, CDCl3) d: 1.62-1.81 (m, 6H), 1.91-2.12 (m,
6H), 3.62 (m, 2H), 4.01 (m, 2H), 5.52 (m, 2H), 7.02 (m,
1H), 7.05 (m, 1H), 7.11 (m, 1H), 7.15 (m, 1H), 7.18 (m,
1H), 7.23 (m, 1H), 7.38 (m, 1H), 7.47 (m, 1H), 7.61 (m,
1H); HRMS (ESI), m/z, 388.1441; Anal. Calc. for
C22H25ClO4: C 67.95; H 6.48. Found: C 68.03; H 6.49.
Biphenyl-3,4¢-diol (8a)
1
Yield 90%, as a white solid, H NMR (300 MHz,
3,4¢-Bis(4-aminibenzoyloxy)-3¢-fluoro-biphenyl (10b)
Yield 98%, as a yellow powder, IR (KBr) v/cm-1
3884, 3473, 3362, 3237, 2979, 2943, 2872, 2683, 2522,
2336, 2120, 2010, 1991, 1703, 1610, 1596, 1506, 1460,
1443, 1392, 1316, 1261, 1221, 1167, 1051, and 1012; 1H
NMR (300 MHz, CDCl3) d: 6.17 (s, 2H), 6.24 (s, 2H), 6.47
(m, 4H), 7.25 (m, 1H), 7.43-7.60 (m, 4H), 7.70-7.83 (m,
5H), 7.93 (m, 1H); HRMS (ESI), m/z, 442.1329; Anal.
Calc. for C26H19FN2O4: C 70.58; H 4.33; N 6.33. Found: C
70.19; H 4.52; N 6.41.
CDCl3) d: 6.72 (m, 1H), 6.82 (m, 2H), 6.95 (m, 2H), 7.22
(m, 1H), 7.42 (m, 2H), 9.41 (s, 1H), 9.52 (s, 1H); HRMS
(ESI), m/z, 186.0681; Anal. Calc. for C12H10O2: C 77.40; H
5.41. Found: C 77.09; H 5.50.
3¢-Fluoro-biphenyl-3,4¢-diol (8b)
1
Yield 83%, as a white solid, H NMR (300 MHz,
CDCl3) d: 6.71 (m, 1H), 6.81 (m, 1H), 6.85 (m, 1H), 6.95
(m, 1H), 7.05 (m, 1H), 7.15 (m, 1H), 7.21 (m, 1H), 9.41 (s,
1H), 9.52 (s, 1H); HRMS (ESI), m/z, 204.0586; Anal. Calc.
for C12H9FO2: C 70.58; H 4.44. Found: C 70.33; H 4.52.
3¢-Chloro-biphenyl-3,4¢-diol (8c)
3,4¢-Bis(4-aminibenzoyloxy)-3¢-chloro-biphenyl (10c)
Yield 96%, as a yellow powder, IR (KBr) v/cm-1
3874, 3475, 3364, 3239, 2969, 2933, 2875, 2680, 2525,
2338, 2122, 2011, 1993, 1701, 1617, 1601, 1512, 1468,
1446, 1390, 1318, 1263, 1223, 1168, 1052, and 1002; 1H
NMR (300 MHz, CDCl3) d: 6.19 (s, 2H), 6.23 (s, 2H), 6.53
(m, 4H), 7.23 (m, 1H), 7.42-7.63 (m, 4H), 7.72-7.95 (m,
6H); HRMS (ESI), m/z, 458.1033; Anal. Calc. for
1
Yield 87%, as a white solid, H NMR (300 MHz,
CDCl3) d: 6.75 (m, 1H), 6.83 (m, 1H), 6.87 (m, 1H), 6.97
(m, 1H), 7.03 (m, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 9.41 (s,
1H), 9.52 (s, 1H); HRMS (ESI), m/z, 220.0291; Anal.
Calc. for C12H9ClO2: C 65.32; H 4.11. Found: C 65.42; H
4.09.