3834
B.-Y. Lu et al. / Tetrahedron Letters 51 (2010) 3830–3835
Figure 3. Fluorescence micrographs of vesicles of (a) 14, (b) 19, and (c) 22, formed in methanol (1 mg/mL) in the presence of rhodamine B (1%) after being purified by dialysis
for 5 days.
9. Cai, W.; Wang, G.-T.; Du, P.; Wang, R.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc.
2008, 130, 13450–13459.
10. Yuan, L.; Sanford, A. R.; Feng, W.; Zhang, A.; Zhu, J.; Zeng, H.; Yamato, K.; Li, M.;
ferent positions. Therefore, their stacking patterns may be differ-
ent—to form membranes of mono- or multi-layered structures.
However, the results, together with our previous studies, well
demonstrate that DOAEO is a new, unique, and useful amphiphilic
amide-alkane-hybridized chain for the formation of vesicular
structures in polar organic solvents. Because DOAEO can modulate
the self-assembly of aromatic backbones of varying shape, in the
future we will design new large electron-rich and deficient conju-
gated disc or linear backbones to assemble vesicular structures,
which are expected to exhibit new interesting electron or energy
transfer properties within their membranes.
Ferguson, J. S.; Gong, B. J. Org. Chem. 2005, 70, 10660–10669.
11. Typical procedure: A solution of compounds 4b (92 mg, 0.20 mmol) and 6b
(0.10 g, 0.20 mmol) in the mixture of chloroform (5 mL) and DMSO (5 mL) was
stirred at 60 °C for 12 h and then concentrated with a rotavapor. The obtained
slurry was dissolved in chloroform (10 mL). The solution was washed with
water (5 mL Â 2) and brine (5 mL) and dried over sodium sulfate. Upon
removal of the solvent, the crude product was recrystallized from ether and
petroleum ether to give macrocycle 1b as a yellow solid (0.18 g, 95%). 1H NMR
(300 MHz, CDCl3) d: 11.10 (s, 6H), 9.07 (s, 6H), 9.02 (s, 6H), 8.21 (s, 6H), 6.68 (s,
6H), 6.39 (s, 6H), 4.17–3.23 (m, 180H). 13C NMR (75 MHz, CDCl3) d: 160.7,
160.5, 159.5, 140.8, 137.6, 125.7, 116.5, 113.9, 97.8, 96.5, 71.8, 70.6, 70.4, 70.3
(d), 69.8, 69.4, 68.5, 68.0, 58.9, 58.8. MS (MALDI-TOF): m/z 2845.2 [M+Na]+.
HRMS (MALDI-TOF): calcd for
2844.34782.
C132H204N12O54Na: 2844.3475. Found:
Acknowledgments
12. (a) Lin, J.-B.; Xu, X.-N.; Jiang, X.-K.; Li, Z.-T. J. Org. Chem. 2008, 73, 9403–9410;
(b) Lin, J.-B.; Wu, J.; Jiang, X.-K.; Li, Z.-T. Chin. J. Chem. 2009, 27, 117–122; (c) Xu,
X.-N.; Wang, L.; Lin, J.-B.; Wang, G.-T.; Jiang, X.-K.; Li, Z.-T. Chem. Eur. J. 2009,
15, 5763–5774; (d) Xu, X.-N.; Wang, L.; Li, Z.-T. Chem. Commun. 2009, 6634–
6636.
13. (a) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F.
Angew. Chem., Int. Ed. 2002, 41, 899–952; (b) Corbett, P. T.; Leclaire, J.; Vial, L.;
West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652–
3711.
We thank National Natural Science Foundation of China
(20921091, 20732007, 20974118), Ministry of Science and Tech-
nology of China (2007CB808001), and Science and Technology
Commission of Shanghai Municipality (09XD1405300) for financial
support.
14. Ferguson, J. S.; Yamato, K.; Liu, R.; He, L.; Zeng, X. C.; Gong, B. Angew. Chem., Int.
Ed. 2009, 48, 3150–3154.
References and notes
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17. Typical procedure: A solution of compounds 17 (0.16 g, 0.12 mmol) and 2018
(11 mg, 0.06 mmol) in methanol (8 mL) was stirred at room temperature for
16 h and then concentrated with
a rotavapor. The resulting residue was
recrystallized from methanol to give compound 19a as a yellow solid (0.13 g,
85%). 1H NMR (300 MHz, CDCl3) d: 11.43 (s, 2H), 10.92 (s, 2H), 8.51(s, 2H),
8.41(s, 2H), 7.40 (d, J = 12 Hz, 4H), 6.80 (s, 2H), 4.81 (s, 4H), 4.75 (s, 8H), 4.15 (s,
12H), 3.31 (s, 12H), 3.19 (s, 12H). 13C NMR (75 MHz, CDCl3): 169.6, 168.5,
167.4, 162.3, 151.0, 150.7, 149.7, 140.8, 128.6, 120.3, 117.8, 108.2, 72.9, 68.9,
47.4, 46.6, 41.2, 41.0, 32.0, 29.6, 29.5, 29.0 (d), 27.8, 27.2, 22.8, 14.3. MS
(MALDI-TOF): 2584.8 [M+K+H2O]+. HRMS (MALDI-TOF): calcd for
C
142H246N16O22Na [M+Na]+: 2550.8514. Found: 2550.8498.
18. Borisenko, K. B.; Zauer, K.; Hargittai, I. J. Phys. Chem. 1996, 100, 19303–19309.
19. Compound 22: A mixture of compounds 17 (96 mg, 0.08 mmol), 20 (13 mg,
0.08 mmol), and 21 (10 mg, 0.04 mmol) in the mixture of chloroform (6.4 mL)
and methanol (1.6 mL) was stirred at room temperature for 48 h and then
concentrated. The resulting slurry was subjected to column chromatography
(CH2Cl2/MeOH 10:1) to give a crude product, which was further recrystallized
from petroleum ether and ethyl acetate to give 22 as an orange-yellow solid
(10 mg, 10%). 1H NMR (300 MHz, CDCl3) d: 11.26 (t, J = 3.6 Hz, 2H), 10.83 (s,
4H), 10.39 (d, J = 6.0 Hz, 2H), 8.42 (s, 2H), 8.23 (d, J = 1.8 Hz, 2H), 7.84–7.80 (m,
8. Richter, D. T.; Lash, T. D. Tetrahedron 2001, 57, 3657–3672.