Y. Zhao et al. / Tetrahedron 68 (2012) 1547e1551
1551
by column chromatography on silica gel with dichloromethane to
yield monoimide as white solid (1.893 g, 26.7%). Mp 181e183 ꢀC, EI-
MS (m/z): 379, 1H NMR (400 M, CDCl3)
8.82 (s, 4H, H-Naphthalene
rings); 1.43e1.28 (m, 12H,
4.20 (t, 2H, J¼7.6 Hz, N-methylene);
octyl chain);
0.88 (t, 3H, J¼6.6 Hz, octyl chain methyl).
d
6.96e6.97 (m, 5H,1HePh, p N; 4HePhe, m Ethylene);
d
6.96 (s, 4H,
d
H-ethylene);
d
4.24 (t, 2H, J¼7.9 Hz, N-octyl methylene);
1.81 (t,
0.91 (t, 3H,
(ppm)
d
2H, H-octyl chain); d 1.29 (m, 10H, H-octyl chain); d
d
d
J¼9.2 Hz, H-octyl methane). 13C NMR (150 M, CDCl3):
d
d
163.24, 162.92, 148.23, 147.91, 146.79, 146.61, 141.86, 133.57, 133.49,
133.39, 132.92, 131.93, 131.55, 130.91, 130.84, 130.63, 129.53, 129.19,
128.37, 128.20, 127.53, 127.24, 125.61, 125.38, 122.17, 121.93, 41.56,
31.70, 29.80, 29.70, 28.63, 27.61, 23.15, 14.55. HRMS (ESI): calcd for
C68H54N4O4 990.4145, Found 990.4140.
4.1.5. N-(4-bromophenyl)-N0-octyl-naphthalene-1,4,5,8-tetracarbo-
xylic acid bisimide(8)25. Compound 7 (1.89 g, 5.0 mmol) and 4-
bromoaniline (1.72 g, 10 mmol) were stirred under nitrogen in
dry DMF (50 ml) at 130 ꢀC for 12 h. When the solution was cooling
down, it was washed with water and extracted with dichloro-
methane. The organic layer was dried over anhydrous sodium
sulfate. The product was purified by column chromatography on
silica gel with dichloromethane as eluent yielding 1.247 g yellow
Acknowledgements
This work was supported by Chinese Academy of Science.
solid (46.9%). Mp 258e260 ꢀC, 1H NMR (400M, CDCl3):
4H, H-naphthalene rings);
d
8.77 (s,
7.70 (d, 2H, J¼8.4 Hz, HePhe, o N);
4.20 (t, 2H, J¼7.6 Hz, N-
References and notes
d
d
7.22 (d, J¼8.4 Hz, HePhe, o Br);
d
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d 1.43e1.25 (m, 12H, H-octyl chain); d 0.87 (t, 3H,
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d
(ppm) 163.07, 162.96, 133.89, 133.11, 131.74, 131.30, 130.58,
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4.1.6. N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N0-
octyl-naphthalene-1,4,5,8-tetracarboxylic acid (2)26. A solution of 8
(1.24 g, 2.33 mmol), bis(pinacolato)diboron (0.519 g, 2.71 mmol),
2(dppf) (0.348 g, 0.42 mmol), and KOAc (0.67 g, 7 mmol) in dry 1,4-
dioxane (15 ml) was stirred at 80 ꢀC for 12 h under N2. After the
solution was cooling down to room temperature, it was washed
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rough product with petroleum ether, and then filtered, the solid
was used in the next step without further purification.) 1H NMR:
14. Zhuang, X. D.; Chen, Y.; Li, B. X.; Ma, D. G.; Zhang, B.; Li, Y. X. Chem. Mater. 2010,
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d
8.78 (s, 4H, H-naphthalene rings);
o N);
7.34 (d, 2H, J¼8.0 Hz, HePhe, o B);
octyl methylene); 1.37 (m, 12H, 4CH3);
chain);
d
8.03 (d, 2H, J¼8.0 Hz, HePhe,
d
d
4.2 (t, 2H, J¼7.6 Hz, N-
d
d
1.26 (m, 12H, H-octyl
d
0.88 (t, 3H, J¼6.0 Hz, H-octyl chain, methyl); MS(EI):580.
4.1.7. TPADPNI26. Compound 1 (696 mg, 1 mmol), compound 2
(1.6 g, 3 mmol), Pd(PPh3)4 (124 mg, 0.1 mmol), and Cs2CO3 (3.258 g,
10 mmol) were added to a 100 ml three necked Schlenk flask.
Vacuum nitrogen cycles were repeated for three times. Then DMF
(40 ml) and H2O were injected and the mixture was heated at
120 ꢀC for 20 h. After the solution was cooling to room temperature,
it was washed with water and extracted with dichloromethane
twice. The organic layers were dried over anhydrous sodium sul-
fate, filtered and concentrated in vacuum. The residue was purified
with silica gel chromatography yielding 246 mg pale yellow pow-
der (24.8%). Mp: decomposing before melting. (Td¼354.3 ꢀC) 1H
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23. Mallegol, T.; Gmouh, S.; Meziane, M. A. A.; Blanchard-Desce, M.; Mongin, O.
NMR(600 M, CDCl3):
7.77 (d, 2H, J¼8.3 Hz, HePhe, o N-naphthalene);
J¼8.4 Hz, HePhe, m Ne2Phe); 7.39 (d, 2H, J¼8.3 Hz, HePhe, m
N-naphthalene); 7.16 (d, 2H,
7.22 (t, 2H, J¼7.9 Hz, HePh, m N);
J¼8.5 Hz, HePhe, m Ne2Phe); 7.06e7.09 (m, 6H, 2HePh, o
Ne2Phe; 4HePhe, o N-Phe);
7.03 (d, 8H, J¼7.6 Hz, o Ethylene);
d
8.84e8.87 (d,d, 4H, H-naphthalene rings);
Synthesis-Stuttgart 2005, 1771e1774.
24. Wiederrecht, G. P.; Niemczyk, M. P.; Svec, W. A.; Wasielewski, M. R. J. Am. Chem.
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d
d
7.53 (d, 2H,
d
25. Chaignon, F.; Falkenstrom, M.; Karlsson, S.; Blart, E.; Odobel, F.; Hammarstrom,
d
d
L. Chem. Commun. 2007, 64e66.
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A.; Sellinger, A. J. Mater. Chem. 2009, 19, 3228e3237.
d
d