H. Uno et al. / Tetrahedron Letters 46 (2005) 1981–1983
1983
Fritz, S. E.; Martin, S. M.; Frisbie, C. D.; Ward, M. D.;
Toney, M. F. J. Am. Chem. Soc. 2004, 126, 4084.
thermal decomposition of 3. When the sodium salt of 3
was heated at 100 °C in DMF,12 the obtained product
was 6,13-pentacenequinone (5, 89%) probably due to
air oxidation of pentacene formed.
3. Takahashi, T.; Kitamura, M.; Shen, B.; Nakajima, K. J.
Am. Chem. Soc. 2000, 122, 12876; Anthony, J. E.; Brooks,
J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001,
123, 9482; Anthony, J. E.; Eaton, D. L.; Parkin, S. R. Org.
Lett. 2002, 4, 15; Meng, H.; Bendikof, M.; Mitchell, G.;
Helgeson, R.; Wudl, F.; Bao, Z.; Siegrist, T.; Kloc, C.;
Chen, C.-H. Adv. Mater. 2003, 15, 1090; Payne, M. M.;
Delcamp, J. H.; Parkin, S. R.; Anthony, J. E. Org. Lett.
2004, 6, 1609; Sakamoto, Y.; Suzuki, T.; Kobayashi, M.;
Gao, Y.; Fukai, Y.; Inoue, Y.; Sato, F.; Tokito, S. J. Am.
Chem. Soc. 2004, 126, 8138.
In conclusion, we achieved the first preparation of the
readily soluble and stable photo precursor of pentacene,
and showed the efficient conversion to pentacene both in
solid and in solution. This method provides not only a
new synthetic method of pentacene derivatives, which
are not easily accessible due to low solubility and stabil-
ity, but also new preparative methodology for the penta-
cene-based devices. Further studies about the device
preparation are under way.
4. (a) Brown, A. R.; Pomp, A.; de Leeuw, D. M.; Klaassen,
D. B. M.; Havinaga, E. E.; Herwig, P.; Mullen, K. J. Appl.
¨
Phys. 1996, 79, 2136; Herwig, P. T.; Mullen, K. Adv.
¨
Mater. 1999, 11, 480; (b) Miao, Q.; Nguyen, T.-Q.;
Someya, T.; Blanchet, G. B.; Nuckolls, C. J. Am. Chem.
Soc. 2003, 125, 10284; Vets, N.; Smet, M.; Dehaen, W.
Tetrahedron Lett. 2004, 45, 7287.
Acknowledgements
Partial financial support from Canon inc. is greatly
acknowledged. We also thank Professor Nagao Azuma
for permission of our use of an ultra-high Hg lamp.
5. Very recently, deposition of pentacene from a precursor by
photochemically generated proton and its application for
an EFT device were reported, see: Weidkamp, K. P.;
Afzali, A.; Tromp, R. M.; Hamers, R. J. J. Am. Chem.
Soc. 2004, 126, 12740.
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9. Selected data for 1: Yellow crystals, mp 320 °C; H NMR
d (CDCl3) 7.94 (4H, s), 7.84 (4H, m), 7.52 (4H, m) and
5.31 (2H, s); 13C NMR d (CDCl3) 185.2, 133.6, 131.9,
127.9, 127.0, 125.4, and 60.6; IR (KBr) 1755, 1736, and
756 cmÀ1; UV–vis (e, CHCl3) 463 (1400) nm.
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