Synthesis, Characterization, and Gas Permeation Properties

82
Dendronization of Ethyl Cellulose
(m, 8H, CH3CH2), 1.49–1.55 (m, 8H, CH3CH2CH2), 1.62–1.68 (m, 4H,
C(=O)NHCH2CH2CH2), 1.99–2.06 (m, 2H, (CH3CH2CH2)2CH)), 2.15 (brs, 1H,
CH2NHCH2), 2.56–2.64 (m, 4H, C(=O)NHCH2CH2CH2), 3.29–3.34 (m, 4H,
C(=O)NHCH2CH2CH2), 6.63 (brs, 2H, C(=O)NH); 13 C NMR (CDCl3, 100 MHz,
25 °C, ppm): 14.0, 20.8, 29.1, 35.2, 37.0, 46.7, 47.5, 176.4; HRMS(FAB): [MH] + ,
calcd for C22H45N3O2 384.3585, found 384.3588; anal. calcd for C22H45N3O2: C,
68.88; H, 11.82; N, 10.95; O,8.35, found: C, 68.69; H, 11.68; N, 10.98; O, 8.65.
4-(bis(3-(2-Propylpentanamido)propyl)amino)-4-oxobutanoic acid
(G1-b-ІІ). The reaction of G1-b-І (25 g, 0.065 mol) with succinic anhydride (9.79 g,
0.097 mol) and the purification of the product were carried out in the same way as that
for the synthesis of G1-a-ІІ. Yield 95%, white solid, mp 151 °C, 1 H NMR (CD3OD,
400 MHz, 25 °C, ppm): 0.84 (t, J = 6.8 Hz, 12H, CH3CH2), 1.18–1.28 (m, 8H,
CH3CH2), 1.42–1.53 (m, 8H, CH3CH2CH2), 1.60–1.79 (m, 4H,
C(=O)NHCH2CH2CH2), 2.09–2.17 (m, 2H, (CH3CH2CH2)2CH)), 2.53–2.58 (m, 4H,
CH2CH2C(=O)OH), 3.06–3.17 (m, 4H, C(=O)NHCH2CH2CH2), 3.22–3.34/3.28 (m,
4H, C(=O)NHCH2CH2CH2), 7.87 (brs, 1H, C(=O)NH), 8.05 (brs, 1H, C(=O)NH); 13 C
NMR (CD3OD, 100 MHz, 25 °C, ppm): 14.4, 21.8, 28.8, 30.1, 36.4, 37.6, 44.6, 46.8,
47.9, 173.9, 176.4, 178.7, 179.1; HRMS(FAB): [MH] + , calcd for C26H49N3O5
484.3745, found 484.3749; anal. calcd for C26H49N3O5: C, 64.56; H, 10.21; N, 8.69; O,
16.54, found: C, 64.59; H, 9.98; N, 8.62; O, 16.81.
N,N′-(3,3′-Azanediylbis(propane-3,1-diyl))bis(2-ethylhexanamide) (G1-c-І).
It was synthesized by using 2-ethylhexanoic acid (44.9 mL, 0.312 mol) rather than
2-ethylbutanoic acid whereas the rest of the conditions and procedure were the same as
those for the synthesis of G1-a-І. Yield 89%, white solid, mp 50 °C, 1 H NMR
(CDCl3, 400 MHz, 25 °C, ppm): 0.81–0.85 (m, 12H, CH3CH2), 1.16–1.28 (m, 8H,
CH3CH2CH2CH2), 1.31–1.44 (m, 4H, CH3CH2CH2CH2), 1.50–1.67 (m, 8H, CH3CH2,
C(=O)NHCH2CH2CH2), 1.85–1.94 (m, 2H, (CH3CH2CH2CH2)(CH3CH2)CH), 2.28
(brs, 1H, CH2NHCH2), 2.55–2.63 (m, 4H, C(=O)NHCH2CH2CH2), 3.27–3.37 (m, 4H,
C(=O)NHCH2CH2CH2), 6.57 (brs, 2H, C(=O)NH); 13 C NMR (CDCl3, 100 MHz,