K.C. Majumdar et al. / Tetrahedron 65 (2009) 152–157
157
115.1, 115.3, 120.2, 121.6, 122.6, 123.0, 124.7, 129.3, 130.9, 138.5,
139.2, 140.0, 147.0, 160.1, 162.3, 173.3. [
Anal. Calcd for C50H68N2O4: C, 78.91; H, 9.01; N, 3.68%. Found: C,
78.58; H, 9.97; N, 3.52%.
Anal. Calcd for C79H119NO6: C, 80.49; H, 10.18; N, 1.19%. Found: C,
80.05; H, 10.12; N, 1.35%.
a
]
D
ꢀ18.6 (c 0.16, CHCl3).
Acknowledgements
3.2.6. Compound 8a
We thank the DST (New Delhi) for financial assistance. Two of us
(S.C. and N.P.) are thankful to the CSIR (New Delhi) for their fel-
lowships. We also thank the Material Science Department of the
IACS (Kolkata) for HRXRD facilities.
A mixture of amine 7 (100 mg, 0.168 mmol) and 9-anthracene
aldehyde (34 mg, 0.168 mmol) was refluxed in absolute ethanol
(10 mL) in the presence of a catalytic amount of glacial acetic acid
for 9 h. Yellow solid was precipitated out from the reaction mixture.
It was collected, washed with ethanol, and dried in vacuum.
Yield 85%; mp 113–115 ꢁC; UV (CHCl3) lmax: 254, 204 nm; IR
References and notes
(KBr) nmax: 1255, 1622, 1731, 2866, 2942 cmꢀ1 1H NMR (CDCl3,
;
1. Kitzerow, H. S.; Bahr, Ch Chirality in Liquid Crystals; Springer: New York, NY,
2002.
400 MHz): 0.66–2.36 (51H, m, aliphatic and cholesteric protons are
overlapped), 4.02 (2H, t, J 6.4 Hz, OCH2), 4.57–4.60 (1H, m, OCH),
5.38 (1H, d, J 4.0 Hz, ]CH), 7.0 (2H, d, J 8.7 Hz, ArH), 7.42 (2H, d, J
8.7 Hz, ArH), 7.49–7.52 (2H, m, ArH), 7.54–7.57 (2H, m, ArH), 8.03
(2H, d, J 8.3 Hz, ArH), 8.54 (1H, s, ArH), 8.81 (2H, d, J 8.8 Hz, ArH),
9.69 (1H, s, CH]N). 13C NMR (CDCl3, 125 MHz): 12.2, 19.1, 19.7, 21.4,
22.9, 23.2, 24.2, 24.6, 25.2, 26.0, 28.2, 28.4, 28.6, 29.3, 32.2, 32.3,
35.0, 36.1, 36.5, 37.0, 37.4, 38.5, 39.9, 40.1, 42.7, 50.4, 56.5, 57.0, 68.4,
74.2, 115.5, 122.7, 123.0, 125.2, 125.7, 127.4, 128.1, 129.3, 130.6, 130.9,
2. Goodby, J. W. Nature 1989, 337, 449.
3. Goodby, J. W.; Slaney, A. J.; Booth, C. J.; Nishiyama, I. J. D.; Vuijk, P.; Toyne, K. J.
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26, 589.
131.7, 140.0, 145.8, 158.0, 158.4, 173.4. [
a]
ꢀ20.0 (c 0.16, CHCl3).
D
Anal. Calcd for C54H69NO3: C, 83.14; H, 8.91; N, 1.80%. Found: C,
82.92; H, 9.55; N, 1.57%.
11. Lee, D. W.; Jin, J.-I.; Laguerre, M.; Achard, M. F.; Hardouin, F. Liq. Cryst. 2000,
27, 145.
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1393.
3.2.7. Compound 8b
A mixture of amine 7 (100 mg, 0.168 mmol) and ferrocene alde-
hyde (35 mg, 0.168 mmol) was refluxed in absolute ethanol (10 mL)
in the presence of a catalytic amount of glacial acetic acid for 8 h. Ash
color solid was precipitated out from the reaction mixture. It was
collected, washed with ethanol, and dried in vacuum.
Yield 85%; mp 173–175 ꢁC; UV (CHCl3) lmax: 244, 228, 217 nm; IR
nmax: 1255,1622,1732, 2866, 2935 cmꢀ1; 1H NMR (CDCl3, 400 MHz):
0.67–2.33 (51H, m, aliphatic and cholesteric protons are over-
lapped), 3.95 (2H, t, J 6.03 Hz, OCH2), 4.23 (5H, s, ferrocenyl H), 4.45
(2H, s, ferrocenyl H), 4.59–4.61 (1H, m, OCH), 4.77 (2H, s, ferrocenyl
H), 5.37 (1H, d, J 4.5 Hz, ]CH), 6.87 (2H, d, J 8.6 Hz, ArH), 7.1 (2H, d, J
8.6 Hz, ArH), 8.32 (1H, s, CH]N). 13C NMR (CDCl3, 125 MHz): 12.2,
19.1, 19.7, 21.4, 22.9, 23.2, 24.2, 24.6, 25.2, 26.0, 28.2, 28.4, 28.6, 29.3,
29.4, 30.0, 31.3, 32.2, 32.3, 34.9, 36.1, 36.5, 36.9, 37.3, 38.5, 39.9, 40.1,
42.7, 50.4, 56.5, 57.0, 68.3, 68.7, 69.2, 70.0, 71.4, 73.5, 74.1, 74.2,115.3,
116.0,116.8,122.0,123.0,140.0,146.2,157.5,159.9,173.4,193.8, 207.3.
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Iyi, N.; Taketoshi, F. Liq. Cryst. 2003, 30, 681.
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17. Yelamaggad, C. V.; Mathews, M. Liq. Cryst. 2003, 30, 125.
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20. Mery, S.; Haristoy, D.; Nicoud, J.-F.; Guillon, D.; Monobe, H.; Shimizu, Y. J. Mater.
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21. Lin, Y.-C.; Weiss, R. G. Liq. Cryst. 1989, 4, 367.
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25. Imrie, C. T. Struct. Bond. 1990, 95, 150.
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[
a
]
D ꢀ16.0 (c 0.16, CHCl3). Anal. Calcd for C50H69FeNO3: C, 76.38; H,
8.92; N, 1.75%. Found: C, 76.50; H, 9.10; N, 1.90%.
29. Dierking, I. Liq. Cryst. 1999, 26, 83.
3.2.8. Compound 8c
30. Wen, J.; Chen, H.; Shen, Y. Liq. Cryst. 1999, 26, 1833.
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Mol. Cryst. Liq. Cryst. 2001, 363, 1.
41. Yelamaggad, C. V.; Nagamani, S. A.; Hiremath, U. S.; Rao, D. S. S.; Prasad, S. K. Liq.
Cryst. 2001, 28, 1581.
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28, 1009.
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1367.
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47. Mallia, A.; Tamaoki, N. J. Mater. Chem. 2003, 219.
48. Tamaoki, N.; Kruk, G.; Matsuda. J. Mater. Chem. 1999, 9, 2381.
A mixture of amine 7 (100 mg, 0.168 mmol) and aldehyde 5
(100 mg, 0.168 mmol) was refluxed in absolute ethanol (10 mL) in
the presence of a catalytic amount of glacial acetic acid for 1 h. Pale
yellow solid was precipitated out from the reaction mixture. It was
collected, washed with ethanol, and dried in vacuum.
Yield 98%; mp 163–165 ꢁC; UV (CHCl3) lmax: 335, 283, 240 nm;
IR (KBr) nmax: 1255, 1621, 1731, 2866, 2935 cmꢀ1 1H NMR (CDCl3,
;
400 MHz): 0.67–2.33 (102H, m, aliphatic and cholesteric protons
are overlapped), 3.94 (2H, t, J 6.3 Hz, OCH2), 3.99 (2H, t, J 6.3 Hz,
OCH2), 4.59–4.77 (2H, m, OCH), 5.35 (2H, d, J 3.6 Hz, ]CH), 6.88
(2H, d, J 8.7 Hz, ArH), 6.93 (2H, d, J 8.5 Hz, ArH), 7.23 (2H, d, J 8.5 Hz,
ArH), 7.85 (2H, d, J 8.7 Hz, ArH), 8.37 (1H, s, CH]N). 13C NMR
(CDCl3, 125 MHz): 12.2, 18.8, 19.7, 21.4, 22.9, 23.2, 24.2, 24.6, 25.1,
25.2, 25.9, 26.0, 28.2, 28.4, 28.6, 29.2, 29.3, 32.2, 32.2, 34.9, 34.9,
36.1, 36.5, 36.9, 37.3, 38.5, 39.9, 40.1, 42.7, 50.4, 56.5, 57.0, 68.6, 68.1,
68.2, 74.2, 74.2, 115.0, 115.3, 122.4, 123.0, 123.0, 129.7, 130.6, 140.0,
145.4, 157.8, 158.2, 161.8, 173.3, 173.4. [
a]
ꢀ24.0 (c 0.16, CHCl3).
D