SYNTHESIS AND AGGREGATION PROPERTIES OF THIACALIX[4]ARENE
435
under reflux, the precipitate was filtered off, and the
filtrate was evaporated. The residue was treated with
an aqueous solution of Na2S2O3, the mixture was
stirred for 2 h at room temperature, and the precipitate
was filtered off, washed with water, and dried under
reduced pressure (water-jet pump).
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 14-03-00 921) and by the Ministry of Education
and Science of the Russian Federation.
REFERENCES
4,4′,4″,4′′′-[5,11,17,23-Tetra-tert-butyl-2,8,14,20-
tetrathiacalix[4]arene-25,26,27,28-tetrayltetrakis-
(oxy)]tetrakis[N-acetyl-N-(2-hydroxyethyl)butan-
amide] (1,3-alternate) (11). Yield 58%, mp 179°C. IR
spectrum, ν, cm–1: 3307 (OH), 2957 (C–Har1om, t-Bu),
1741 (C=O), 1650 (C=O), 1263 (COC). H NMR
spectrum (CDCl3), δ, ppm: 1.23 s (36H, t-Bu), 1.44 t
(8H, OCH2CH2OH, J = 8.0 Hz), 1.68 br.s (4H, OH),
1.99 t (8H, OCH2CH2OH, J = 8.0 Hz), 2.06 s (12H,
Me), 3.45 m (8H, OCH2CH2CH2), 3.88 t (8H,
OCH2CH2CH2, J = 8.0 Hz), 4.12 t (8H, OCH2CH2CH2,
J = 4.0 Hz), 7.33 s (8H, Harom). Mass spectrum, m/z:
1427 [M + Na]+, 1443 [M + K]+. C72H102N4O16S4.
Calculated: M 1406.
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4,4′,4″,4′′′-[5,11,17,23-Tetra-tert-butyl-2,8,14,20-
tetrathiacalix[4]arene-25,26,27,28-tetrayltetrakis-
(oxy)]tetrakis[N-(2-hydroxyethyl)-N-(1-oxopropyl)-
butanamide] (1,3-alternate) (12). Yield 79%,
mp 158°C. IR spectrum, ν, cm–1: 3369 (OH), 2962
(C–Harom, t-Bu), 1739 (C=O), 1649 (C=O), 1267
8. Dworak, A., Polym. Bull., 1997, vol. 38, p. 7.
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1
(COC). H NMR spectrum (CDCl3), δ, ppm: 1.14 t
(12H, CH2CH3, J = 8.0 Hz), 1.23 s (36H, t-Bu), 1.44 t
(8H, OCH2CH2OH, J = 8.0 Hz), 1.77 br.s (4H, OH),
2.06 t (8H, OCH2CH2OH, J = 8.0 Hz), 2.33 q (8H,
CH2CH3), 3.46 m (8H, OCH2CH2CH2), 3.89 t (8H,
OCH2CH2CH2, J = 8.0 Hz), 4.14 t (8H, OCH2CH2CH2,
J = 4.0 Hz), 7.35 s (8H, Harom). Mass spectrum, m/z:
1483 [M + Na]+. C76H108N4O16S4. Calculated: M 1460.
4,4′,4″,4′′′-[5,11,17,23-Tetra-tert-butyl-2,8,14,20-
tetrathiacalix[4]arene-25,26,27,28-tetrayltetrakis-
(oxy)]tetrakis[N-benzoyl-N-(2-hydroxyethyl)butan-
amide] (1,3-alternate) (13). The precipitate was sub-
jected to column chromatography on alumina using
acetonitrile as eluent. Yield 20%, mp 90°C. IR spec-
trum, ν, cm–1: 3380 (OH), 2961 (C–Harom, t-Bu), 1724
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1
(C=O), 1646 (C=O), 1270 (COC). H NMR spectrum
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(CDCl3), δ, ppm: 1.18 br.s (36H, t-Bu), 1.35 m (8H,
OCH2CH2OH), 2.05–2.14 m (8H, OCH2CH2OH),
3.60–3.68 m (8H, OCH2CH2CH2), 3.87 m (8H,
OCH2CH2CH2), 4.25–4.38 m (8H, OCH2CH2CH2),
7.32 s (8H, Harom), 7.28–7.55 m (12H, m-H, p-H),
7.77 t (4H, o-H, J = 8.0 Hz), 8.01 t (4H, o-H, J =
8.0 Hz). Mass spectrum, m/z: 1692 [M + K]+.
C92H108N4O16S4. Calculated: M 1652.
19. Gordon, A.J. and Ford, R.A., The Chemist’s Companion,
New York: Wiley, 1972.
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