Paper
NJC
1e: Yield 85%, m.p. 105 1C, 1H NMR (400 MHz, CDCl3, TMS): 2.431 (s, 3H; CH3), 1.808–1.739 (m, 2H; CH2), 1.267–1.224
d 12.165 (s, 1H, NH), 7.457 (d, 1H; CH), 7.023 (d, 1H; CH), (m, 24H; CH2), 0.913–0.897 (t, 3H; CH3). MS (EI): m/z 352.20
2.590–2.553 (t, 2H; CH2), 1.827–1.752 (m, 2H, CH2), 1.424–1.264 [M]+. FTIR (KBr): 3427, 3180, 3080, 2919, 2850, 1697, 1585,
(m, 22H, CH2), 0.910 (t, 3H; CH3). MS (EI): m/z 324.53 [M]+. FTIR 1462, 1409, 1381, 1311, 1280, 1111, 953, 832, 723, 527 cmÀ1
.
(KBr): 3171, 2916, 2849, 1688, 1577, 1468, 1321, 1279, 1166,
1065, 959, 874, 805, 778, 624, 520 cmÀ1
3g: Yield 80%, m.p. 111 1C, 1H NMR (400 MHz, CDCl3, TMS):
d 12.005 (s, 1H, NH), 7.075 (s, 1H; CH) 2.531–2.494 (t, 2H; CH2),
.
1f: Yield 80%, m.p. 121 1C, 1H NMR (400 MHz, CDCl3, TMS): 2.437 (s, 3H; CH3), 1.806–1.752 (m, 2H; CH2), 1.398–1.266
d 12.053 (s, 1H, NH), 7.458 (d, 1H; CH), 7.026 (d, 1H; CH), (m, 26H; CH2), 0.912–0.893 (t, 3H; CH3). MS (EI): m/z 366.63
2.585–2.547 (t, 2H; CH2), 1.888–1.771 (m, 2H, CH2), 1.424–1.265 [M]+. FTIR (KBr): 3432, 3181, 2919, 2850, 2274, 1697, 1588,
(m, 24H, CH2), 0.911–0.876 (t, 3H; CH3). MS (EI): m/z 338.31 1472, 1380, 1312, 1166, 1112, 1067, 962, 831, 782, 622 cmÀ1
.
[M]+. FTIR (KBr): 3174, 2917, 2849, 1686, 1581, 1468, 1380,
1322, 1288, 1110, 1067, 959, 873, 777, 718, 625, 520 cmÀ1
3h: Yield 79%, m.p. 108 1C, 1H NMR (400 MHz, CDCl3, TMS):
d 12.173 (s, 1H, NH), 7.088 (s, 1H; CH), 2.533–2.515 (t, 2H; CH2),
.
1g: Yield 83%, m.p. 117 1C, 1H NMR (400 MHz CDCl3, TMS): 2.497 (s, 3H; CH3), 1.787–1.752 (m, 2H; CH2), 1.331–1.266
d 11.9855 (s, 1H, NH), 7.462 (d, 1H; CH), 7.032 (d, 1H; CH), (m, 28H; CH2), 0.912–0.878 (t, 3H; CH3). MS (EI): m/z 380.35
2.590–2.365 (t, 2H; CH2), 1.827–1.752 (m, 2H, CH2), 1.437–1.264 [M]+. FTIR (KBr): 3428, 3179, 2919, 2850, 1696, 1583, 1465,
(m, 26H, CH2), 0.911–0.877 (t, 3H; CH3). MS (EI): m/z 351.84 1411, 1380, 1311, 1278, 1168, 1108, 793, 722 cmÀ1
.
[M]+. FTIR (KBr): 3170, 2917, 2849, 1685, 1576, 1469, 1379,
1321, 1272, 1168, 1064, 959, 875, 778, 718, 624, 520 cmÀ1
.
Characterization
1h: Yield 79%, m.p. 102 1C, 1H-NMR (400 MHz, CDCl3, FTIR spectra were recorded on a Perkin Elmer – RX FTIR
TMS): d 11.865 (s, 1H, NH), 7.458 (d, 1H; CH), 7.024 (d, 1H; instrument. Solid samples were recorded as an intimate mix-
1
CH), 2.581–2.544 (t, 2H; CH2), 1.828–1.753 (m, 2H, CH2), 1.430– ture with powdered KBr. The H-NMR spectra were measured
1.265 (m, 28H, CH2), 0.912–0.878 (t, 3H; CH3). MS (EI): m/z using a Bruker AVANCE, 400 MHZ with TMS as internal
366.18 [M]+. FTIR (KBr): 3176, 2924, 2851, 1683, 1580, 1465, standard. Morphologies of all reported xerogels (dried gels)
1379, 1323, 1275, 1169, 1065, 962, 872, 774, 718, 623, 520 cmÀ1
.
were investigated using scanning electron microscopy (SEM)
2e: Yield 72%, m.p. 100 1C, 1H NMR (400 MHz, CDCl3, TMS): (JEOL JSM5610 LV microscope). For SEM study, the hot sample
d 12.165 (s, 1H, NH), 6.506 (s, 1H; CH), 2.507–2.478 (t, 2H; CH2), gel liquid was placed over the SEM sample holder and allowed
2.346 (s, 3H; CH3), 1.768–1.712 (m, 2H; CH2), 1.330–1.266 to form the gel. Then, the sample was subjected to dryness
(m, 22H; CH2), 0.911–0.880 (t, 3H; CH3). MS (EI): m/z 338.39 under normal room temperature and pressure and coated with
[M]+. FTIR (KBr): 3358, 3164, 2928, 2854, 1672, 1553, 1469, carbon (1e, 1h, 3e–3g) and gold sputtering (3h). The morpho-
1314, 1235, 1115, 1079, 974, 772, 564 cmÀ1
.
logies of synthesized Ag and ZnO nanoparticles were investi-
2f: Yield 70%, m.p. 83 1C, 1H NMR (400 MHz, CDCl3, TMS); d gated using transmission electron microscopy (TEM) (Philips
13.360 (s, 1H, NH), 6.652 (s, 1H; CH) 2.698–2.660 (t, 2H; CH2), CM 200) in the working voltage of 20–200 kV. TEM studies were
2.511 (s, 3H; CH3), 1.801–1.765 (m, 2H; CH2), 1.377–1.311 carried out by placing a small amount of the corresponding
(m, 24H; CH2), 0.908–0.874 (t, 3H; CH3). MS (EI): m/z 352.29 compound dispersed in ethanol–water on carbon-coated copper
[M]+. FTIR (KBr): 3348, 3152, 2914, 2849, 1670, 1552, 1461, grids and dried by slow evaporation. The range of diameter of
1317, 1233, 1117, 1085, 976, 778, 561 cmÀ1
.
the synthesized nanoparticles was determined by measuring the
2g: Yield 74%, m.p. 89 1C, 1H NMR (400 MHz, CDCl3, TMS); diameters of o100 nanoparticles (from smallest to largest) using
d 13.345 (s, 1H, NH), 6.526 (s, 1H; CH), 2.557–2.422 (t, 2H; CH2), TEM images. Powder diffraction patterns of neat xerogel 1e
2.262 (s, 3H; CH3), 1.777–1.642 (m, 2H; CH2), 1.331–1.208 (methanol, slowly evaporated) and xerogel loaded with silver
(m, 26H; CH2), 0.911–0.877 (t, 3H; CH3). MS (EI): m/z 366.40 nanoparticles were recorded on XPERT Philips (CuKa radiation).
[M]+. FTIR (KBr): 3359, 3160, 2923, 2859, 1675, 1559, 1463, The silver nano-particles loaded on gelator fibres was subjected
1329, 1239, 1121, 1090, 982, 770, 569 cmÀ1
.
to powder diffraction studies using Bruker D8 (CuKa radiation)
2h: Yield 71%, m.p. 96 1C, 1H NMR (400 MHz, CDCl3, TMS): diffractometer. Single crystal X-ray study of compounds 1c, 1d,
d 13.178 (s, 1H, NH), 6.559 (s, 1H; CH), 2.501–2.463 (t, 2H; CH2), 2d and 3c was carried out on single crystal X-ray diffractometer
2.238 (s, 3H; CH3), 1.756–1.720 (m, 2H; CH2), 1.331–1.267 (Xcalibur, EOS, Gemini diffractometer). All structures were ana-
(m, 28H; CH2), 0.912–0.896 (t, 3H; CH3). MS (EI): m/z 380.20 lysed using Olex1.2 software24 and refined using ShelXL refine-
[M]+. FTIR (KBr): 3355, 3154, 2918, 2851, 1678, 1552, 1468, ment package.25
1311, 1233, 1111, 1089, 976, 777, 560 cmÀ1
3e: Yield 78%, m.p. 105 1C, 1H NMR (400 MHz, CDCl3, TMS):
.
Gelation test
d 12.191 (s, 1H, NH), 7.085 (s, 1H; CH), 2.546–2.526 (t, 2H; CH2), A weighted amount of potential gelator (10 mg) and a measured
2.451 (s, 3H; CH3), 1.772–1.767 (m, 2H; CH2), 1.278–1.266 volume (1 ml) of selected pure organic solvent–water were
(m, 22H; CH2), 0.912–0.878 (t, 3H; CH3). MS (EI): m/z 338.19 placed into a capped test tube (outer diameter 10 mm and
[M]+. FTIR (KBr): 3179, 3060, 2912, 2847, 1682, 1589, 1466, length 75 mm), and the system was heated in an oil or water
1418, 1381, 1303, 1279, 1181, 958, 719, 526 cmÀ1
.
bath, until the dissolution of solid materials. The solution was
3f: Yield 82%, m.p. 121 1C, 1H NMR (400 MHz, CDCl3, TMS): cooled to room temperature and finally, the test tube was
d 11.986 (s, 1H, NH), 7.062 (s, 1H; CH), 2.532–2.494 (t, 2H; CH2), turned upside down to observe if the solution inside could still
728 | New J. Chem., 2015, 39, 721--730
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