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Can. J. Chem. Vol. 91, 2013
Tris-(((4-butoxyphenyl)methylidene)aminophenoxyethyl)
benzene-1,3,5-tricarboxylate (5b)
6H), 6.95 (d, 6H), 6.93 (d, 6H), 4.72 (t, 6H), 4.33 (t, 6H), 4.00 (t, 6H),
1.79 (m, 6H), 1.45 (m, 6H), 1.35 (m, 60H), 0.87 (t, 9H). 13C NMR
(CDCl3, 100 MHz, ppm) ␦: 164.92, 161.76, 158.33, 156.82, 145.98,
135.10, 131.15, 130.37, 129.33, 122.23, 115.35, 114.71, 68.26, 66.18,
64.18, 32.02, 29.85, 29.66, 29.40, 29.29, 26.12, 22.80, 14.24. EI-MS
m/z: 1518 (M+ + 1).
Yield: 60%; mp 172–174 °C. IR (KBr, cm−1): 2943 and 2871
(–CH2str), 1724 (C=Ostr ester), 1605 and 1508 (C=Cstr aromatic), 1473
1
(–CHben), 1242 and 1109 (C-O-Cstr of ester), 1162 (C-O-Cstr). H NMR
(CDCl3, 500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d, 6H),
7.13 (d, 6H), 6.95 (d, 6H), 6.93 (d, 6H), 4.72 (t, 6H), 4.33 (t, 6H), 4.00
(t, 6H), 1.78 (m, 6H), 1.50 (m, 6H), 0.98 (t, 9H). 13C NMR (CDCl3,
100 MHz, ppm) ␦: 164.92, 161.54, 158.32, 156.82, 145.98, 135.10,
131.15, 130.37, 129.33, 122.23, 115.35, 114.71, 67.94, 66.18, 64.18,
31.32, 19.32, 13.96. EI-MS m/z: 1097 (M+ + 1).
Tris-(((4-hexadecyloxyphenyl)methylidene)aminophenoxyethyl)
benzene-1,3,5-tricarboxylate (5h)
Yield: 60%; mp 148 °C. IR (KBr, cm−1): 2919 and 2851 (–CH2str),
1732 (C=Ostr ester), 1611 and 1572 and 1509 (C=C str aromatic), 1463
1
(–CHben), 1246 (C-O-Cstr of ester), 1163 (C-O-Cstr). H NMR (CDCl3,
Tris-(((4-hexyloxyphenyl)methylidene)aminophenoxyethyl)
benzene-1,3,5-tricarboxylate (5c)
500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d, 6H), 7.13
(d, 6H), 6.95 (d, 6H), 6.93 (d, 6H), 4.72 (t, 6H), 4.33 (t, 6H),3.99 (t, 6H),
1.79 (m, 6H), 1.45 (m, 6H), 1.25 (m, 72H), 0.87 (t, 9H).13C NMR (CDCl3,
100 MHz, ppm) ␦: 164.92, 161.76, 158.33, 156.82, 145.98, 135.10,
131.15, 130.37, 129.33, 122.23, 115.35, 114.71, 68.26, 66.18, 64.18,
32.00, 29.80, 29.68, 29.47, 29.29, 26.12, 22.80, 14.24. EI-MS m/z: 1602
(M+ + 1).
Yield: 60%; mp 164–166 °C. IR (KBr, cm−1): 2929 and 2863
(–CH2str), 1734 (C=Ostr ester), 1612 and 1508 (C=Cstr aromatic), 1461
(–CHben), 1226 and 1108 (C-O-Cstr of ester). 1H NMR (CDCl3,
500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d, 6H), 7.13 (d,
6H), 6.95 (d, 6H), 6.93 (d, 6H), 4.72 (t, 6H), 4.33 (t, 6H), 4.00 (t, 6H),
1.79 (m, 6H), 1.46 (m, 6H), 1.34 (m, 12H), 0.91 (t, 9H). 13C NMR (CDCl3,
100 MHz, ppm) ␦: 164.92, 161.76, 158.33, 156.82, 145.98, 135.10,
131.15, 130.37, 129.33, 122.23, 115.35, 114.71, 68.26, 66.18, 64.18,
31.68, 29.25, 25.80, 22.71, 14.16. EI-MS m/z: 1181.5 (M+ + 1).
Tris-(((4-ethoxyphenyl)methylidene)aminophenoxybutyl)
benzene-1,3,5-tricarboxylate (6a)
Yield: 60%; mp 146 °C. IR (KBr, cm−1): 2954 and 2871 (–CH2str),
1729 (C=Ostr ester), 1623 (–C=Nstr– imine), 1605 and 1510 (C=Cstr
aromatic), 1472 (–CHben), 1238 (C-O-Cstr of ester), 1165 (C-O-Cstr). 1H
NMR (CDCl3, 500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d,
6H), 7.13 (d, 6H), 6.94 (d, 6H), 6.89 (d, 6H), 4.46 (t, 6H), 4.07 (q, 6H),
4.02 (t, 6H), 1.98 (m, 12H), 1.43 (t, 9H). 13C NMR (CDCl3, 100 MHz,
ppm) ␦: 165.08, 161.48, 158.05, 157.30, 145.33, 134.59, 131.44, 130.35,
129.34, 122.18, 114.99, 114.69, 67.54, 65.55, 63.70, 26.10, 25.64, 14.86.
EI-MS m/z: 1096 (M+).
Tris-(((4-octyloxyphenyl)methylidene)aminophenoxyethyl)
benzene-1,3,5-tricarboxylate (5d)
Yield: 60%; mp 161–163 °C. IR (KBr, cm−1): 2930 and 2864
(–CH2str), 1730 (C=Ostr ester), 1610 and 1572 and 1508 (C=Cstr aro-
1
matic), 1469 (–CHben), 1242 (C-O-Cstr of ester), 1164 (C-O-Cstr). H
NMR (CDCl3, 500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d,
6H), 7.13 (d, 6H), 6.95 (d, 6H), 6.93 (d, 6H), 4.72 (t, 6H), 4.33 (t, 6H),
4.00 (t, 6H), 1.79 (m, 6H), 1.46 (m, 6H), 1.30 (m, 24H), 0.89 (t, 9H). 13
C
Tris-(((4-butoxyphenyl)methylidene)aminophenoxybutyl)
benzene-1,3,5-tricarboxylate (6b)
NMR (CDCl3, 100 MHz, ppm) ␦: 164.92, 161.76, 158.33, 156.82,
145.98, 135.10, 131.15, 130.37, 129.33, 122.23, 115.35, 114.71, 68.26,
66.18, 64.18, 31.91, 29.46, 29.34, 29.29, 26.12, 22.76, 14.22. EI-MS m/z:
1264.4 (M+).
Yield: 60%; mp 154 °C. IR (KBr, cm−1): 2956 and 2871 (–CH2str),
1731 (C=Ostr ester), 1625 (–C=Nstr– imine), 1606 and 1510 (C=Cstr
aromatic), 1471 (–CHben), 1243 (C-O-Cstr of ester), 1166 (C-O-Cstr). 1H
NMR (CDCl3, 500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d,
6H), 7.13 (d, 6H), 6.94 (d, 6H), 6.89 (d, 6H), 4.46 (t, 6H), 4.03 (t, 6H),
Tris-(((4-decyloxyphenyl)methylidene)aminophenoxyethyl)
benzene-1,3,5-tricarboxylate (5e)
Yield: 60%; mp 155–157 °C. IR (KBr, cm−1): 2925 and 2855
(–CH2str), 1731 (C=Ostr ester), 1608 and 1572 and 1508 (C=Cstr aro-
4.00 (t, 6H), 1.97 (m, 12H), 1.78 (m, 6H), 1.50 (m, 6H), 0.98 (t, 9H). 13
C
NMR (CDCl3, 100 MHz, ppm) ␦: 165.08, 161.71, 158.05, 157.30, 145.33,
134.59, 131.44, 130.35, 129.29, 122.18, 114.99, 114.69, 67.93, 67.54,
65.55, 31.32, 26.10, 25.64, 19.32, 13.97. EI-MS m/z: 1181.6 (M+ + 1).
1
matic), 1469 (–CHben), 1253 (C-O-Cstr of ester), 1162 (C-O-Cstr). H
NMR (CDCl3, 500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d,
6H), 7.13 (d, 6H), 6.95 (d, 6H), 6.93 (d, 6H), 4.72 (t, 6H), 4.33 (t, 6H),
4.00 (t, 6H), 1.79 (m, 6H), 1.45 (m, 6H), 1.31 (m, 36H), 0.88 (t, 9H). 13
C
Tris-(((4-hexyloxyphenyl)methylidene)aminophenoxybutyl)
benzene-1,3,5-tricarboxylate (6c)
NMR (CDCl3, 100 MHz, ppm) ␦: 164.92, 161.76, 158.33, 156.82,
145.98, 135.10, 131.15, 130.37, 129.33, 122.23, 115.35, 114.71, 68.26,
66.18, 64.18, 32.00, 29.66, 29.50, 29.42, 29.29, 26.12, 22.76, 14.22.
EI-MS m/z: 1349.6 (M+ + 1).
Yield: 60%; mp 151 °C. IR (KBr, cm−1): 2933 and 2868 (–CH2str),
1731 (C=Ostr ester), 1625 (–C=Nstr– imine), 1607 and 1510 (C=Cstr
aromatic), 1472 (–CHben), 1245 (C-O-Cstr of ester), 1166 (C-O-Cstr). 1H
NMR (CDCl3, 500 MHz, ppm) ␦: 8.84 (s, 3H), 8.35 (s, –CH=N), 7.78 (d,
6H), 7.13 (d, 6H), 6.94 (d, 6H), 6.89 (d, 6H), 4.46 (t, 6H), 4.03 (t, 6H),
4.00 (t, 6H), 1.97 (m, 12H), 1.79 (m, 6H), 1.46 (m, 6H), 1.34 (m, 12H),
0.90 (t, 9H). 13C NMR (CDCl3, 100 MHz, ppm) ␦: 165.08, 161.71,
158.05, 157.30, 145.33, 134.59, 131.44, 130.35, 122.18, 114.99, 114.69,
68.25, 67.54, 65.55, 31.67, 29.25, 26.10, 25.79, 25.64, 22.70, 14.15.
EI-MS m/z: 1264.5 (M+).
Tris-(((4-dodecyloxyphenyl)methylidene)aminophenoxyethyl)
benzene-1,3,5-tricarboxylate (5f)
Yield: 60%; mp 150–152 °C. IR (KBr, cm−1): 2924 and 2855
(–CH2str), 1730 (C=Ostr ester), 1611 and 1572 and 1508 (C=Cstr aro-
1
matic), 1473 (–CHben), 1245 (C-O-Cstr of ester), 1164 (C-O-Cstr). H
NMR (CDCl3, 500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d,
6H), 7.13 (d, 6H), 6.95 (d, 6H), 6.93 (d, 6H), 4.72 (t, 6H), 4.33 (t, 6H),
4.00 (t, 6H), 1.79 (m, 6H), 1.46 (m, 6H), 1.33 (m, 48H), 0.88 (t, 9H). 13
C
Tris-(((4-octyloxyphenyl)methylidene)aminophenoxybutyl)
benzene-1,3,5-tricarboxylate (6d)
NMR (CDCl3, 100 MHz, ppm) ␦: 164.92, 161.76, 158.33, 156.82,
145.98, 135.10, 131.15, 130.37, 129.33, 122.23, 115.35, 114.71, 68.26,
66.18, 64.18, 32.00, 29.75, 29.71, 29.66, 29.50, 29.42, 29.29, 26.12,
22.76, 14.22. EI-MS m/z: 1434 (M+ + 1).
Yield: 60%; mp 147 °C. IR (KBr, cm−1): 2926 and 2859 (–CH2str),
1729 (C=Ostr ester), 1611 and 1509 (C=Cstr aromatic), 1468 (–CHben),
1243 (C-O-Cstr of ester), 1163 (C-O-Cstr). 1H NMR (CDCl3, 500 MHz,
ppm) ␦: 8.84 (s, 3H), 8.35 (s, –CH=N), 7.78 (d, 6H), 7.13 (d, 6H), 6.94
(d, 6H), 6.89 (d, 6H), 4.46 (t, 6H), 4.03 (t, 6H), 4.00 (t, 6H), 1.97 (m,
12H), 1.79 (m, 6H), 1.46 (m, 6H), 1.31 (m, 24H), 0.88 (t, 9H). 13C NMR
(CDCl3, 100 MHz, ppm) ␦: 165.08, 161.71, 158.05, 157.30, 145.33,
134.59, 131.44, 130.35, 129.29, 122.18, 114.99, 114.69, 68.25, 67.54,
65.55, 31.91, 29.44, 29.34, 29.28, 26.11, 25.64, 22.70, 14.15. EI-MS m/z:
1348.5 (M+).
Tris-(((4-tetradecyloxyphenyl)methylidene)aminophenoxyethyl)
benzene-1,3,5- tricarboxylate (5g)
Yield: 60%; mp 152–154 °C. IR (KBr, cm−1): 2920 and 2852
(–CH2str), 1732 (C=Ostr ester), 1611 and 1509 (C=Cstr aromatic), 1463
1
(–CHben), 1245 (C-O-Cstr of ester), 1163 (C-O-Cstr). H NMR (CDCl3,
500 MHz, ppm) ␦: 8.88 (s, 3H), 8.35 (s, –CH=N), 7.78 (d, 6H), 7.13 (d,
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