3668
F. YANG ET AL.
Compound 4a. 1H NMR (600 MHz, CDCl3) d ppm: 0.60 (m, 16H, SiCH2),
0.95 (d, 42H, J ¼ 6.6 Hz, CH3), 1.23–1.88 [m, 15H, (CH2)3CH2OAr, COOCH2CH2
and SiCH2CH], 2.27 (t, 2H, J ¼ 7.2 Hz, CH2COO), 2.77 (s, 3H, NCH3), 3.94 (t,
2H, J ¼ 6.6 Hz, OCH2), 4.02 (t, 2H, J ¼ 6.6 Hz, CH2OAr), 4.22 (d, 1H, J ¼ 9.6 Hz,
NCH2), 4.87 (s, 1H, ArCH), 4.95 (d, 1H, J ¼ 9.6 Hz, NCH2), 6.92 (d, 2H, J ¼ 8.4
ArH), 7.68 (bs, 2H, ArH); 13C NMR (150 MHz, CDCl3) d ppm: 8.56, 22.43,
22.65, 22.72, 24.07, 24.10, 24.98, 25.90, 25.93, 25.96, 29.27, 34.41, 40.22, 66.47,
67.80, 69.20, 70.21, 77.60, 83.40, 129.01, 136.01, 136.02, 136.80, 137.0, 139.80,
140.13, 140.34, 140.37, 141.76, 141.90, 142.05, 142.19, 142.23, 142.25, 142.30,
142.33, 142.35, 142.38, 142.48, 142.51, 142.76, 142.80, 142.89, 143.20, 143.36,
144.62, 144.84, 144.93, 145.36, 145.45, 145.49, 145.52, 145.55, 145.68, 145.71,
145.76, 146.0, 146.14, 146.16, 146.31, 146.35, 146.37, 146.43, 146.49, 146.52,
146.61, 146.75, 147.03, 147.51, 147.52, 153.90, 154.34, 156.60, 159.30, 173. FT-IR
(KBr) v=cmꢀ1: 3437, 2952, 1737, 1464, 1109, 836, 560, 481. UV-vis: 256, 308, and
429 nm. MS m=z (%): 1840.34 (Mþ, 100). Anal. calcd. for C106H89O15Si8N: C,
69.16; H 4.87; N, 0.76. Found: C, 69.24; H, 5.73; N, 0.67.
Compound 4b. 1H NMR (600 MHz, CDCl3) d ppm: 0.60 (m, 16H, SiCH2),
0.95 (d, 42H, J ¼ 6.6 Hz, CH3), 1.24–1.86 [m, 25H, (CH2)8CH2OAr, COOCH2CH2
and SiCH2CH], 2.28 (t, 2H, J ¼ 7.2 Hz, CH2COO), 2.77 (s, 3H, NCH3), 3.93 (t,
2H, J ¼ 6.6 Hz, OCH2), 4.01 (t, 2H, J ¼ 6.6 Hz, CH2OAr), 4.22 (d, 1H, J ¼ 9.6 Hz,
NCH2), 4.87 (s, 1H, ArCH), 4.95 (d, 1H, J ¼ 9.6 Hz, NCH2), 6.92 (d, 2H, J ¼ 8.4
ArH), 7.69 (bs, 2H, ArH); 13C NMR (150 MHz, CDCl3) d ppm: 8.57, 22.43, 22.65,
22.72, 24.07, 24.10, 25.22, 25.89, 25.93, 26.32, 29.41, 29.51, 29.56, 29.63, 29.64,
29.75, 34.57, 40.22, 66.38, 68.19, 69.20, 70.22, 77.61, 83.42, 128.90, 136.01, 136.80,
136.99, 139.79, 140.11, 140.33, 140.37, 141.75, 141.89, 142.05, 142.19, 142.22,
142.25, 142.30, 142.33, 142.35, 142.38, 142.48, 142.51, 142.77, 142.80, 142.88,
143.20, 143.36, 144.61, 144.84, 144.92, 145.36, 145.45, 145.49, 145.52, 145.55,
145.68, 145.71, 145.76, 146.0, 146.13, 146.16, 146.31, 146.34, 146.37, 146.42,
146.48, 146.52, 146.62, 146.75, 147.04, 147.50, 147.52, 153.92, 154.35, 156.62,
159.41, 174.01. FT-IR (KBr) v=cmꢀ1: 3440, 2952, 1737, 1464, 1108, 836, 572, 483.
UV-vis: 256, 307, and 430 nm. MS m=z (%): 1910.22 (Mþ, 100). Anal. calcd. for
C
111H99O15Si8N: C, 69.76; H, 5.22; N, 0.73. Found: C, 69.86; H, 5.17; N, 0.64.
ACKNOWLEDGMENTS
Financial support from the National Natural Science Foundation of China
(No. 20402002), Fujian Natural Science Foundation of China (No. 2009J01019),
and Program for Excellent Young Researchers in University of Fujian Province
(JA10056) were greatly acknowledged. Thanks go to Prof. Lei Zhu at Case Western
Reserve University for supplying the materials.
REFERENCES
1. Sawamura, M.; Kawai, K.; Matsuo, Y.; Kanie, K.; Kato, T.; Nakamura, E. Stacking of
conical molecules with a fullerene apex into polar columns in crystals and liquid crystals.
Nature 2002, 419, 702–705.