S. Pappalardo et al.
FULL PAPER
+
[
M + H + MeOH] . C141
H
168
N
16
O
15 (2326.9): calcd. C 72.78, H
[7] P. Lhoták, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron
1
996, 52, 12399–12408.
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7.28, N 9.63; found C 72.44, H 7.40, N 9.51.
[
TAPB Dodecaamino Tris(calixarene) Dendron 14: Off-white powder
from MeOH (0.035 g, 74% yield); m.p. Ͼ250 °C. H NMR ([D
DMSO): δ = 9.98 (br. s, 3 H, NH), 7.80–7.68 (m, 15 H, ArH core),
1
1
6
]-
[
[
6
.00, 5.99, 5.91 (3ϫ s, ratio 1:1:2, 24 H, ArH calix), 4.4–4.0 (hump,
4 H, NH ), 4.19, 4.17 (2ϫ d, J = 11.0, 10.5 Hz, 6 H each, 12 H,
Ar), 3.78, 3.66, 3.61 (3ϫ t, J = 7.3 Hz, ratio 1:1:2, 24 H,
), 2.80, 2.78 (2ϫ d, J = 12.1 Hz, 6 H each, 12 H, ArCH Ar),
.39 (t, J = 7.3 Hz, 6 H, CH CO), 2.20 (quint., J = 7.3 Hz, 6 H,
CH CH CO), 1.85 (m, 18 H, OCH CH CH ), 0.92, 0.91 (2ϫ t, J
7.3 Hz, ratio 1:2, 27 H, OCH CH CH ]-
) ppm. 13C NMR ([D
DMSO): δ = 170.9, 147.6, 147.5, 142.3, 142.1, 142.0, 134.6, 134.14,
2
2
ArCH
OCH
2
2
2
2
2
2
2
2
2
3
=
2
2
3
6
1
2
34.09, 127.3, 119.3, 114.2, 114.1, 76.4, 76.2, 73.9, 33.2, 30.9, 25.5,
2.7, 22.6, 21.1, 10.4, 10.3 ppm. ESI MS: m/z = 1205.7 [M + H +
[
12] a) L. Di Costanzo, S. Geremia, L. Randaccio, R. Purrello, R.
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2+
+
+
Na] , 2421.2 [M + H + MeOH] , 2443.1 [M + Na + MeOH] .
15 (2388.0): calcd. C 73.93, H 7.22, N 8.80; found C
4.12, H 7.35, N 8.71.
C
7
147 171 15
H N O
1
4536–14537; c) F. G. Gulino, R. Lauceri, L. Frish, T. Evan-
TAPT Dodecaamino Tris(calixarene) Dendron 16: Brownish-red
powder from MeOH (0.042 g, 88% yield); m.p. Ͼ250 °C. H NMR
Salem, Y. Cohen, R. De Zorzi, S. Geremia, L. Randaccio, D.
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4, 436–445.
1
(
[D
6
]DMSO): δ = 10.28 (s, 3 H, NH), 8.68, 7.87 (2ϫ d, J = 8.5 Hz,
H each, 1,4-phenylene core), 6.03, 6.01, 5.91 (3ϫ s, ratio 1:1:2,
4 H, ArH calix), 4.24 (br. s, 24 H, NH ), 4.21, 4.18 (2ϫ d, J =
2.2 Hz, 6 H each, ArCH Ar), 3.81, 3.68, 3.62 (3ϫ t, J = 7.5 Hz,
), 2.81, 2.79 (2ϫ d, J = 12.2 Hz, 6 H each,
Ar), 2.45 (t, J = 7.0 Hz, 6 H, CH C=O), 2.23 (quint., J =
.0 Hz, 6 H, CH CH C=O), 1.89–1.82 (m, 18 H, OCH CH CH ),
.926, 0.920 (2ϫ t, 7.5 Hz, ratio 1:2, 27 H,
CH CH ]DMSO): δ = 171.4, 170.1,
) ppm. 13C NMR ([D
47.6, 147.4, 143.6, 142.3, 142.1, 142.0, 134.7, 134.1, 134.0, 129.7,
29.6, 118.6, 114.2, 114.1, 76.4, 76.1, 73.8, 33.3, 30.8, 25.3, 22.7,
6
2
1
[13] A. D’Urso, D. A. Cristaldi, M. E. Fragalà, G. Gattuso, A. Pap-
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2
2
ratio 1:1:2, 24 H, OCH
ArCH
7
0
2
[
2
2
2
2
2
2
3
J
=
OCH
2
2
3
6
1
1
2
[15]
a) M. Mazik, W. Radunz, W. Sicking, Org. Lett. 2002, 4, 4579–
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2.5, 10.4, 10.3 ppm. ESI MS: m/z = 1196.5 [M + 2H] , 2392 [M
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168 18
+
+
found C 72.21, H 7.19, N 10.60.
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