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84%). H NMR (400 MHz, CDCl3): d 8.40 (d, J ¼ 8.0 Hz, 2H),
8.18–8.14 (m, 6H), 7.67 (dd, J ¼ 8.0 and 2.4 Hz, 2H), 7.00 (d, J ¼
8.8 Hz, 4H), 4.06 (t, J ¼ 6.4 Hz, 4H), 1.83 (quint, J ¼ 6.4 Hz, 4H),
1.52–1.43 (m, 4H), 1.40–0.89 (m, 40H), 0.88 (t, J ¼ 6.8 Hz, 3H).
13C NMR (100 MHz, CDCl3): d 181.45, 164.05, 163.99, 156.01,
135.19, 132.52, 130.95, 129.43, 127.67, 120.57, 120.41, 114.50,
68.42, 31.91, 29.68, 29.66, 29.64, 29.58, 29.54, 29.35, 29.08, 25.97,
22.68, 14.10. Anal. Calcd for C56H72O8: C, 77.03; H, 8.31%.
Found: C, 76.74; H, 8.40%.
´
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Acknowledgements
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J. Org. Chem., 2001, 66, 4517; (c) M. A. Herranz, B. Illescas,
This work was partially supported by a Grant-in-Aid for
Creative Scientific Research of ‘‘Invention of Conjugated
Electronic Structures and Novel Functions’’ (No. 16GS0209)
(T.K.) from the Japan Society for the Promotion of Science
(JSPS) and by the Global COE Program for Chemistry Inno-
vation (T.K. and K.I.) from the Ministry of Education, Culture,
Sports, Science and Technology. We also thank Drs T. Nishi-
mura and T. Hatano of The University of Tokyo for helpful
discussions, and Ms K. Saeki of The University of Tokyo for
help in elemental analyses. T.Y. is grateful for financial support
from the JSPS Research Fellowship for Young Scientists.
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16 The average number of molecules in a column stratum (m) was
estimated according to the following equation: m ¼ (O3NAa2hr)/2M,
where NA is Avogadro’s number, a is the lattice parameter (a ¼ d100
˚
ꢂ 2/O3), h is the thickness (estimated as ca. 3.7 A based on XRD
pattern measurement), r is the density (assumed to be 1 g cmꢁ3) and
M is the molecular weight of the compound.
This journal is ª The Royal Society of Chemistry 2008
J. Mater. Chem., 2008, 18, 4522–4528 | 4527