ACCEPTED MANUSCRIPT
1.49 (m, 28H, −CH2), 1.71–1.79 (m, 4H, −CH2), 3.92−4.00 (m, 4H, −OCH2), 6.90−7.00 (m, 4H,
Ar−H), 7.72 (d, 1H, Ar−H, J = 8.7 Hz), 7.79 (d, 1H, Ar−H, J = 8.7 Hz) 8.04−8.07 (m, 2H, Ar−H),
8.18 (s, 1H, −N=CH), 9.85 (s, 1H, O=CNH). 13C NMR (75 MHz, CDCl3): δ 14.10, 22.67, 25.98,
29.08, 29.22, 29.34, 29.57, 29.64, 31.80, 31.92, 66.78, 68.24, 68.42, 76.59, 77.01, 77.43, 92.47,
101.37, 114.77, 114.83, 115.17, 128.54, 129.55, 129.89, 131.99, 150.53, 157.49, 162.91, 180.39.
MS (HRFAB): calcd for M+: 604.3989. Found: 604.3991. Anal. Calcd for C36H52N4O4: C, 71.49;
H, 8.67; N, 9.26. Found C, 71.47; H, 8.75; N, 9.28.
4.16.1 (E)-N'-(4-(dodecyloxy)benzylidene)-5-(4-(dodecyloxy)phenyl)-1,3,4-oxadiazole-2-carbo
hydrazide 3b (n = 12)
White solids, mp 187.2 °C. Yield 67%. 1H NMR (300 MHz, CDCl3): δ 0.82 (m, 6H, −CH3), 1.21–
1.49 (m, 36H, −CH2), 1.71–1.79 (m, 4H, −CH2), 3.92−4.00 (m, 4H, −OCH2), 6.90 (d, 2H, Ar−H, J
= 8.7 Hz), 6.99 (d, 2H, Ar−H, J = 8.7 Hz), 7.73 (d, 2H, Ar−H, J = 8.7 Hz), 8.08 (d, 2H, Ar−H, J =
8.7 Hz), 8.18 (s, 1H, −N=CH), 9.92 (s, 1H, O=CNH). 13C NMR (75 MHz, CDCl3): δ 14.09, 22.67,
25.97, 29.08, 29.16, 29.33, 29.56, 29.63, 31.90, 68.24, 68.41, 76.58, 77.00, 77.43, 114.82, 115.17,
125.22, 129.52, 129.86, 131.97, 149.43, 150.64, 161.85, 162.89, 166.97, 190.80. IR (KBr): 3270
(N—H), 3085(N=C—H), 1693 (C=N), 1609 (C=O) cm-1. MS (HRFAB): calcd for M+:
660.4615. Found: 660.4610. Anal. Calcd for C40H60N4O4: C, 72.69; H, 9.15; N, 8.48. Found C,
72.56; H, 9.16; N, 8.52.
4.16.2 (E)-5-(4-(dodecyloxy)phenyl)-N'-(4-(hexadecyloxy)benzylidene)-1,3,4-oxadiazole-2-
carbohydrazide 3b (n = 16)
White solids, mp 182.6 °C. Yield 63%. 1H NMR (300 MHz, CDCl3): δ 0.82–0.87 (m, 6H, −CH3),
1.23–1.50 (m, 44H, −CH2), 1.74–1.79 (m, 4H, −CH2), 3.90−4.04 (m, 4H, −OCH2), 6.89−7.01 (m,
4H, Ar−H), 7.72 (d, 1H, Ar−H, J = 9.0 Hz), 7.79 (d, 1H, Ar−H, J = 9.0 Hz), 8.08 (d, 2H, Ar−H, J =
9.0 Hz), 8.18 (s, 1H, −N=CH), 9.82 (s, 1H, −O=CNH). 13C NMR (75 MHz, CDCl3): δ 14.11, 22.69,
25.97, 29.07, 29.16, 29.36, 29.55, 29.68, 31.92, 66.78, 68.24, 68.44, 76.59, 77.01, 77.44, 114.62,
114.76, 114.83, 125.14, 129.55, 129.89, 131.99, 150.53, 167.02. MS (HRFAB): calcd for M+:
716.5241. Found: 716.5234. Anal. Calcd for C44H68N4O4: C, 73.70; H, 9.56; N, 7.81. Found C,
25