Y.-J. Wang et al. / Tetrahedron 63 (2007) 1695–1705
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4.1.10. [4-(Bis-{4-[(3,4-ditetradecanoxyphenylamino)-
methyl]phenyl}amino)phenyl]methanol (2b, n¼14). Off-
68.85, 114.43, 115.82, 124.13, 128.73, 133.71, 142.04,
146.89, 152.00. Anal. Calcd for C93H144N4O3: C, 81.76;
H, 10.62; N, 4.10. Found: C, 81.58; H, 10.89; N, 3.78.
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white solid. H NMR (CDCl3): d 0.91 (t, J¼6.5 Hz, –CH3,
12H), 1.29–1.48 (m, –CH2, 88H), 1.75–1.84 (m, –CH2,
8H), 3.92–3.97 (m, –OCH2, 8H), 4.23 (s, –NCH2, 4H),
4.67 (s, –CH2OH, 2H), 6.25 (s, Ar–H, 2H), 6.35 (s, Ar–H,
2H), 6.81 (d, J¼8.4 Hz, Ar–H, 2H), 7.05–7.08 (m, Ar–H,
6H), 7.26–7.28 (m, Ar–H, 6H). 13C NMR (CDCl3):
d 14.17, 22.75, 26.17, 29.43, 29.52, 29.57, 29.73, 29.77,
31.99, 48.83, 64.85, 69.11, 71.18, 101.06, 104.39, 117.64,
124.03, 124.20, 128.28, 128.75, 134.01, 135.40, 141.53,
143.76, 146.87, 147.21, 150.80. Anal. Calcd for
C89H143N3O5: C, 80.07; H, 10.80; N, 3.15. Found: C,
79.47; H, 10.45; N, 2.68.
4.1.15. Tris-{4-[(3,4-didecanoxyphenylamino)methyl]-
phenyl}amine (3b, n¼10). 1H NMR (CDCl3): d 0.94
(t, J¼6.6 Hz, –CH3, 18H), 1.33–1.51 (m, –CH2, 84H),
1.78–1.87 (m, –CH2, 12H), 3.86 (m, –OCH2, 12H), 4.25
(s, –NCH2, 6H), 6.23 (dd, J¼8.4, 2.3 Hz, Ar–H, 3H),
6.33 (d, J¼2.0 Hz, Ar–H, 3H), 6.84 (d, J¼8.5 Hz, Ar–H,
3H), 7.09 (d, J¼8.3 Hz, Ar–H, 6H), 7.29 (d, J¼8.3 Hz,
Ar–H, 6H). 13C NMR (CDCl3): d 14.17, 22.74, 26.15,
29.42, 29.50, 29.66, 29.72, 31.97, 48.84, 69.06, 71.29,
100.94, 104.27, 117.54, 124.16, 128.74, 133.91, 141.52,
143.69, 146.91, 150.78. Anal. Calcd for C99H156N4O6:
C, 79.36; H, 10.49; N, 3.74. Found: C, 79.53; H, 10.57;
N, 3.44.
4.1.11. [4-(Bis-{4-[(3,4-dihexadecyloxyphenylamino)-
methyl]phenyl}amino)phenyl]methanol (2b, n¼16). Off-
1
white solid. H NMR (CDCl3): d 0.86 (t, J¼6.6 Hz, –CH3,
12H), 1.24–1.43 (m, –CH2, 104H), 1.71–1.77 (m, –CH2,
8H), 3.87–3.92 (m, –OCH2, 8H), 4.18 (s, –NCH2, 4H),
4.62 (s, –CH2OH, 2H), 6.17 (dd, J¼8.5, 2.1 Hz, Ar–H,
2H), 6.27 (d, J¼2.0 Hz, Ar–H, 2H), 6.76 (d, J¼8.5 Hz,
Ar–H, 2H), 7.01–7.04 (m, Ar–H, 6H), 7.21–7.23 (m,
Ar–H, 6H). 13C NMR (CDCl3): d 14.11, 22.69, 26.11,
29.37, 29.46, 29.52, 29.67, 29.72, 31.94, 48.92, 65.08,
69.09, 71.10, 101.05, 104.38, 117.51, 124.00, 124.21,
128.28, 128.78, 133.71, 135.14, 141.49, 143.72, 146.86,
147.34, 150.76. Anal. Calcd for C97H159N3O5: C, 80.50;
H, 11.07; N, 2.90. Found: C, 80.05; H, 10.93; N, 2.69.
4.1.16. Tris-{4-[(3,4-didodecanoxyphenylamino)methyl]-
1
phenyl}amine (3b, n¼12). H NMR (CDCl3): d 0.87 (t,
J¼6.6 Hz, –CH3, 18H), 1.25–1.44 (m, –CH2, 108H), 1.72–
1.79 (m, –CH2, 12H), 3.88–3.93 (m, –OCH2, 12H), 4.19
(s, –NCH2, 6H), 6.18 (dd, J¼8.5, 2.4 Hz, Ar–H, 3H),
6.28 (d, J¼2.4 Hz, Ar–H, 3H), 6.77 (d, J¼8.6 Hz, Ar–H,
3H), 7.02 (d, J¼8.4 Hz, Ar–H, 6H), 7.23 (d, J¼8.4 Hz,
Ar–H, 6H). 13C NMR (CDCl3): d 14.13, 22.70, 26.11,
29.38, 29.46, 29.52, 29.62, 29.68, 31.94, 48.86, 69.07,
71.12, 100.96, 104.29, 117.54, 124.14, 128.74, 133.85,
141.54, 146.90, 150.76. Anal. Calcd for C111H180N4O6:
C, 79.99; H, 10.89; N, 3.36. Found: C, 79.70; H, 10.77;
N, 3.24.
4.1.12. Tris-{4-[(4-tetradecanoxyphenylamino)methyl]-
phenyl}amine (3a, n¼14). 1H NMR (CDCl3): d 0.96 (t, J¼
6.1 Hz, –CH3, 9H), 1.35–1.51 (m, –CH2, 66H), 1.82 (m,
–CH2, 6H), 3.94 (t, J¼6.1 Hz, –OCH2, 6H), 4.26 (s,
–NCH2, 6H), 6.67 (d, J¼8.6 Hz, Ar–H, 4H), 6.84–6.86 (m,
Ar–H, 6H), 7.10–7.11 (m, Ar–H, 6H), 7.29–7.30 (m,
Ar–H, 6H). 13C NMR (CDCl3): d 14.19, 22.77, 26.17,
29.44, 29.55, 29.69, 29.76, 32.00, 48.93, 68.84, 114.14,
115.84, 124.17, 128.67, 134.05, 142.51, 146.90, 151.79.
Anal. Calcd for C81H120N4O3: C, 81.22; H, 10.10; N, 4.68.
Found: C, 80.78; H, 10.29; N, 4.51.
4.1.17. Tris-{4-[(3,4-ditetradecanoxyphenylamino)-
methyl]phenyl}amine (3b, n¼14). 1H NMR (CDCl3):
d 0.94 (t, J¼6.4 Hz, –CH3, 18H), 1.32–1.51 (m, –CH2,
132H), 1.79–1.87 (m, –CH2, 12H), 3.94–3.99 (m, –OCH2,
12H), 4.25 (s, –NCH2, 6H), 6.22 (dd, J¼8.5, 2.1 Hz,
Ar–H, 3H), 6.33 (d, J¼2.0 Hz, Ar–H, 3H), 6.83 (d,
J¼8.5 Hz, Ar–H, 3H), 7.09 (d, J¼8.3 Hz, Ar–H, 6H), 7.29
(d, J¼8.3 Hz, Ar–H, 6H). 13C NMR (CDCl3): d 14.07,
22.65, 26.06, 29.33, 29.42, 29.47, 29.63, 29.68, 31.89,
48.74, 68.97, 71.03, 100.84, 104.15, 117.47, 124.06,
128.64, 133.83, 141.42, 143.64, 146.82, 150.70. Anal. Calcd
for C123H204N4O6: C, 80.51; H, 11.21; N, 3.05. Found C,
80.07; H, 11.52; N, 2.66.
4.1.13. Tris-{4-[(4-hexadecyloxyphenylamino)methyl]-
phenyl}amine (3a, n¼16). Off-white powder, yield 19%.
1H NMR (CDCl3): d 0.86 (t, J¼6.6 Hz, –CH3, 9H), 1.24–
1.43 (m, –CH2, 78H), 1.69–1.75 (m, –CH2, 6H), 3.86 (t, J¼
6.6 Hz, –OCH2, 6H), 4.19 (s, –NCH2, 6H), 6.62 (d, J¼
8.7 Hz, Ar–H, 6H), 6.77 (d, J¼8.7 Hz, Ar–H, 6H), 7.01 (d,
J¼8.1 Hz, Ar–H, 6H), 7.22 (d, J¼8.3 Hz, Ar–H, 6H). 13C
NMR (CDCl3): d 14.07, 22.67, 26.08, 29.34, 29.44, 29.48,
29.60, 29.68, 31.91, 49.23, 68.87, 114.58, 115.85, 124.13,
128.76, 133.63, 142.07, 146.91, 152.13. Anal. Calcd for
C87H132N4O3: C, 81.51; H, 10.38; N, 4.37. Found: C,
81.55; H, 10.45; N, 4.34.
4.1.18. Tris-{4-[(3,4-dihexadecyloxyphenylamino)-
methyl]phenyl}amine (3b, n¼16). 1H NMR (CDCl3):
d 0.87 (t, J¼6.1 Hz, –CH3, 18H), 1.25–1.43 (m, –CH2,
156H), 1.71–1.80 (m, –CH2, 12H), 3.87–3.93 (m, –OCH2,
12H), 4.18 (s, –NCH2, 6H), 6.17 (dd, J¼8.3, 2.1 Hz, 3H),
6.26 (d, J¼2.0 Hz, Ar–H, 3H), 6.77 (d, J¼8.4 Hz, Ar–H,
3H), 7.02 (d, J¼8.3 Hz, Ar–H, 6H), 7.23 (d, J¼8.3 Hz,
Ar–H, 6H). 13C NMR (CDCl3): d 14.13, 22.71, 26.12,
29.48, 29.53, 29.69, 29.74, 31.95, 48.85, 69.08, 71.13,
100.96, 104.28, 117.57, 124.14, 127.74, 133.87, 141.55,
143.70, 146.91, 150.79. Anal. Calcd for C135H228N4O6:
C, 80.94; H, 11.47; N, 2.80. Found: C, 80.44; H, 11.36;
N, 2.60.
4.1.14. Tris-{4-[(4-octadecyloxyphenylamino)methyl]-
phenyl}amine (3a, n¼18). 1H NMR (CDCl3): d 0.86 (t, J¼
6.7 Hz, –CH3, 9H), 1.28–1.42 (m, –CH2, 90H), 1.69–1.75
(m, –CH2, 6H), 3.86 (t, J¼6.6 Hz, –OCH2, 6H), 4.19 (s,
–NCH2, 6H), 6.61 (d, J¼8.4 Hz, Ar–H, 6H), 6.76 (d, J¼
8.4 Hz, Ar–H, 6H), 7.01 (d, J¼8.4 Hz, Ar–H, 6H), 7.22 (d,
J¼8.4 Hz, Ar–H, 6H). 13C NMR (CDCl3): d 14.10, 22.68,
26.09, 29.35, 29.48, 29.60, 29.67, 29.69, 31.93, 49.14,
4.1.19. Tris-{4-[2-(4-hexadecyloxyphenyl)vinyl]phenyl}-
amine (4a, n¼16). The mixture of (4-methoxybenzyl)-
triphenylphosphonium bromide (1.3 g, 1.93 mmol) and