¨ ¨
A. YILDIRIM AND S. OZTURK
1546
1.42–1.22 (m, 32H, CH2−), 0.87 (t, J = 6.4 Hz, 6H, 2 CH3), 13C NMR (100 MHz,
CDCl3) δ 168.1, 163.7, 158.6, 130.3, 127.7, 114.8, 70.9, 69.7, 67.4, 36.3, 31.9, 29.6, 29.4,
29.1, 29.0, 26.4, 25.4, 22.4, 14.1. Anal calc for C46H70N4O6S2 (839.21): C 65.84, H 8.41,
N 6.68, S 7.64. Found: C 66.79, H 8.35, N 6.22, S 7.31.
2-Tridecyl-5-({[4-(2-{2-[2-(4-{[(5-tridecyl-1,3,4-oxadiazol-2-yl)sulfanyl]me-
thyl}phenoxy)ethoxy]ethoxy}ethoxy)phenyl]methyl}sulfanyl)-1,3,4-oxadiazole 6b (n
= 12)
Intermediate 5b (n = 12) (0.67 g, 2.36 mmol), bis-benzyl chloride (3) (0.47 g,
1.18 mmol), K2CO3 (0.65 g, 4.72 mmol), and DMF (15 mL) were used for the synthesis.
The product was crystallized from acetone/petroleum ether as white crystals. Yield 1.01 g
1
(96%); mp 100–101◦C. IR (KBr): 3039, 1612, 1242. H NMR (400 MHz, CDCl3) δ
7.32–7.30 (m, 4H, Ar), 6.86–6.84 (m, 4H, Ar), 4.39 (s, 4H, 2ArCH2S), 4.10 (t, J = 4.4 Hz,
4H, 2 OCH2CH2OAr), 3.84 (t, J = 4.4 Hz, 4H, 2OCH2CH2OAr), 3.73 (s, 4H, OCH2CH2O),
2.79 (t, J = 7.6 Hz, 4H, 2hetCH2CH2−), 1.74 (quin, J = 7.5 Hz, 4H, 2hetCH2CH2CH2−),
1.42–1.22 (m, 40H, CH2−), 0.87 (t, J = 6.7 Hz, 6H, 2 CH3). 13C NMR (100 MHz,
CDCl3) δ 168.1, 163.7, 158.6, 130.3, 127.7, 114.8, 70.9, 69.7, 67.4, 36.4, 31.9, 29.7, 29.6
(2C), 29.4, 29.3, 29.1, 29.0, 26.4, 25.4, 22.7, 14.1. Anal calc for C50H78N4O6S2 (895.32):
C 67.08, H 8.78, N 6.26, S 7.16. Found: C 67.32, H 8.20, N 6.71, S 6.99.
2-Pentadecyl-5-({[4-(2-{2-[2-(4-{[(5-pentadecyl-1,3,4-oxadiazol-2-yl)sulfanyl]
methyl}phenoxy)ethoxy]ethoxy}ethoxy)phenyl]methyl}sulfanyl)-1,3,4-oxadiazole 6c
(n = 14)
Intermediate 5c (n = 14) (0.47 g, 1.50 mmol), bis-benzyl chloride (3) (0.30 g,
0.75 mmol), K2CO3 (0.41 g, 2.97 mmol), and DMF (15 mL) were used for the synthesis.
The product was crystallized from AcOEt/petroleum ether as white crystals. Yield 0.7 g
1
(98%); mp 103–104◦C. IR (KBr): 3039, 1612, 1242. H NMR (400 MHz, CDCl3) δ
7.32–7.30 (m, 4H, Ar), 6.87–6.84 (m, 4H, Ar), 4.39 (s, 4H, 2ArCH2S), 4.10 (t, J = 4.4 Hz,
4H, 2 OCH2CH2OAr), 3.85 (t, J = 4.8 Hz, 4H, 2OCH2CH2OAr), 3.74 (s, 4H, OCH2CH2O),
2.79 (t, J = 7.6 Hz, 4H, 2hetCH2CH2−), 1.74 (quin, J = 7.6 Hz, 4H, 2hetCH2CH2CH2−),
1.42–1.22 (m, 48H, CH2−), 0.87 (t, J = 6.4 Hz, 6H, 2 CH3). 13C NMR (400 MHz,
CDCl3) δ 168.1, 163.7, 158.6, 130.3, 127.7, 114.8, 70.9, 69.7, 67.4, 36.4, 31.9, 29.7 (3C),
29.6 (2C), 29.4, 29.3, 29.1, 29.0, 26.4, 25.4, 22.7, 14.1. Anal calc for C54H86N4O6S2
(951.42): C 68.17, H 9.11, N 5.89, S 6.74. Found: C 68.32, H 9.04, N 5.71, S 6.99.
2-Hexadecyl-5-({[4-(2-{2-[2-(4-{[(5-hexadecyl-1,3,4-oxadiazol-2-yl)sulfanyl]
methyl}phenoxy)ethoxy]ethoxy}ethoxy)phenyl]methyl}sulfanyl)-1,3,4-oxadiazole 6d
(n = 15)
Intermediate 5d (n = 15) (0.51 g, 1.56 mmol), bis-benzyl chloride (3) (0.31 g,
0.78 mmol), K2CO3 (0.43 g, 3.12 mmol), and DMF (15 mL) were used for the synthesis.
The product was crystallized from AcOEt/petroleum ether as white crystals. Yield 0.75 g
(100%); mp 104 – 105◦C. IR (KBr): 3039, 1608, 1242. 1H NMR (400 MHz, CDCl3) δ 7.32
– 7.30 (m, 4H, Ar), 6.87 – 6.84 (m, 4H, Ar), 4.39 (s, 4H, 2ArCH2S), 4.10 (t, J = 4.8 Hz, 4H,
2 OCH2CH2OAr), 3.85 (t, J = 4.4 Hz, 4H, 2OCH2CH2OAr), 3.74 (s, 4H, OCH2CH2O),
2.79 (t, J = 7.6 Hz, 4H, 2hetCH2CH2−), 1.74 (quin, J = 7.5 Hz, 4H, 2hetCH2CH2CH2−),
1.40–1.23 (m, 52H, CH2−), 0.87 (t, J = 6.7 Hz, 6H, 2 CH3). 13C NMR (100 MHz,
CDCl3) δ 168.1, 163.7, 158.6, 130.3, 127.7, 114.8, 70.9, 69.7, 67.4, 36.4, 31.9, 29.7(3C),
29.6 (2C), 29.4, 29.3, 29.1, 29.0, 26.4, 25.4, 22.7, 14.1. Anal calc for C56H90N4O6S2
(979.48): C 68.27, H 9.26, N 5.72, S 6.55. Found: C 68.02, H 9.24, N 5.71, S 6.86.