利用兩分子的萘環1-溴-8-苯乙炔衍生物於鎳金屬錯合物催化及鋅粉活化下，進行二聚合反應，合成出二苯駢[de,mn]稠四苯的駢環衍生物，其結構為非平面結構。由單晶X-ray分析獲得確認，扭曲角度約為(43.8-66.6o)，並根據X-ray單晶結構鍵長與單鍵、雙鍵的差值分析，及理論計算HOMA可知，中心兩個六環是缺少芳香性的。
在產率調整中，鎳金屬錯合物種類、鋅粉的量、溶劑、及溫度都扮演重要角色。將使用萘環1-溴-8-苯乙炔衍生物、1,2-雙(二苯基膦)乙烷錯合的鎳二價金屬、鋅粉，溶於溶劑1,4-二噁烷中，溫度130-150 ℃反應14小時，此方法皆可利用在鹵素為碘及溴時，的活化可以得到五種二苯駢[de,mn]稠四苯的駢環衍生物，產率為30-69％。並利用四正丁基氟化胺脫矽得到第六種二苯駢[de,mn]稠四苯的駢環衍生物。
光電物理性質方面六種二苯駢[de,mn]稠四苯的駢環衍生物，氧化還原電位也跟一般多苯環芳香化合物類似，吸收波長都介於黃光到紅光區，因此化合物HOMO-LUMO能差1.81-2.12 eV都相當低。

Dibenzo[de,mn]naphthacene annelated derivatives has been generated by nickel-catalyzed cyclodimerization. These structure which has been comfirmed by X-ray single-crystal diffraction analysis is non-planar and twist angle about 43.8-66.6o. The bond length and bond alternation in the crystal structures and HOMA theoretical calculations reveal that the central two six-membered rings lack aromaticity.
Systematic studies of reaction conditions reveal that nickel-catalyst, the amount of zinc powder, slovent and temperature all play key roles in this reaction. The reaction conditions have been optimized. Upon heating 1-bromo-(phenylethynyl)acene with mixture of NiBr2(dppe) and zinc powder in 1,4-dioxane at temperature between 130 to 150 ℃ for 14 hours, we generated 6 kinds of Dibenzo[de,mn]naphthacene annelated derivatives, the isolated yield is between 30% to 69%.
These Dibenzo[de,mn]naphthacene annelated derivatives show similar perfermoce in oxidation-reduction potential as most PAHs compounds show. In optical physical properties, the maximum absorption wavelenth of these compound is between 551 nm to 647nm, which shows small HOMO-LUMO energy gap(1.81-2.12 eV).

1. Klauk, H.; Halik, M.; Zschieschang, U.; Eder, F.; Schmid, G.; Dehm, C. Appl. Phys. Lett. 2003, 82, 4175.
2. Hasegawa, T.; Takeya, J. Sci. Technol. Adv. Mater. 2009, 10, 024314.
3. Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Grandi, M. J. D. J. Am. Chem. Soc. 1996, 118, 2843.
4. Slipchenko, L. V.; Krylov, A. I. J. Chem. Phys. 2003, 118, 6874.
5. Trost, B. M.; Chan D. M. T. J. Am. Chem. Soc. 1979, 101, 6429.
6. Fukui K.; Inoue J.; Kubo T.; Nakazawa S.; Aoki T.; Morita Y.; Yamamoto K.; Sato K.; Shiomi D.; Nakasuji K.; Takui, T. synthetic Metals. 2001, 121, 1824.
7. Tidwell, T. T. Angew. Chem. Int. Ed. 2001, 40, 331.
8. Saunderson, A. Physics Education 1968, 3, 272.
9. Montgomery, L. K.; Huffman, J. C.; Jurczak, E. A.; Grendze, M. P. J. Am. Chem. Soc. 1986, 108, 6004.
10. Kamada, K.; Ohta, K.; Kubo, T.;Shimizu, A.; Morita, Y.; Nakasuji, K.; Kishi, R.; Ohta, S.; Furukawa, S-. I.; Takahashi, H.; Nakano, M. Angew. Chem. Int. Ed. 2007, 46, 3544.
11. Li, Y.; Heng, W. K.; Lee, B. S.; Aratani, N.; Zafra, J. L.; Bao, N.; Lee, R.; Sung, Y. M.; Sun, Z.; Huang, K. W.; Webster, R. D.; Navarrete, J. T. L.; Kim, D.; Osuka, A.; Casado, J.; Ding, J.; Wu, J. J. Am. Chem. Soc. 2012, 134, 14913.
12. Konishi, A.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kish i, R.; Shigeta, Y.; Nakano, M.; Tokunaga, K.; Kamada, K.; Kubo, T. J. Am. Chem. Soc. 2013, 135, 1430.
13. Krygowski, T. M.; Ejsmont, K.; Stepień , B. T.; Cyrański, M. K.; Poater, J.; Solà , M. J. Org. Chem. 2004, 69, 6634.
14. (a) Umeda, R.; Hibi, D.; Miki,K.; Tobe,Y. Pure Appl. Chem. 2010, 82, 871. (b) Harvey, R. G. Polycyclic Aromatic Hydrocarbons, Wiley-VCH, Weinheim, 1997.
15. (a) Clar, E. The Aromatic Sextet, Wiley, New York, 1972. (b) Clar, E. Polycyclic Hydrocarbons, Vol. 1 and Vol. 2, Academic Press, London, 1964.
16. Dewar, M. J. S.; Dougherty, R. C. The PMO Theory of OrganicChemistry, Plenum Press, New York, 1975.
17. (a) Morikawa, T.; Narita, S.; Klein, D. J. J. Chem. Inf. Comput. Sci. 2004, 44, 1891. (b) Randic’, M. Tetrahedron 1975, 31, 1477. (c) Randić, M. Chem. Rev. 2003, 103, 3449.
18. (a) Haigh, C. W.; Mallion, R. B. Mol. Phys. 1970, 18, 767.(b) Mallion, R. B. Proc. R. Soc. London Ser. A 1975, 341, 429.(c) Aihara, J. i. J. Phys. Chem. A 2003, 107, 11553. (d) Mallion, R. B. Croa. Chem. Acta 2008, 81, 227.
19. (a) Mitchell, R. H.; Sondheimer, F. J. Am. Chem. Soc. 1968, 90, 530. (b) Meinwald, J.; Young, J. W. J. Am. Chem. Soc. 1971, 93, 725.
20. (a) Kemp, W.; Storie, I. T.; Tulloch, C. D. J. Chem. Soc. Perkin Trans. 1 1980, 2812. (b) Gleiter, R.; Schaff, H. P.; Rodewald, H.; Jahn, R.; Irngartinger, H. Helv. Chim. Acta 1987, 70, 480.
21. Wu, T. C.; Chen, C. H.; Hibi, D.; Shimizu, A.; Tobe, Y.; Wu, Y-. T. Angew. Chem. Int. Ed. 2010, 49, 7059.
22. Wu, T. C.; Tai, C. C.; Tiao, H. C.; Kuo, M. Y.; Wu, Y. T. Chem. Eur. J. 2011, 17, 1930.
23. Levi, Z. U ; Tilley, T. D. J. Am. Chem. Soc. 2009, 131, 2796.
24. Rivera-Fuentes, P.; Rekowski, M. V. W.; Schweizer, W B.; Gisselbrecht, J. P.; Boudon, C.; Diederich, F. O. Org. Lett., 2012, 14, 4066.
25. Veller, B. V.; Robinson, D.; Swager, T. M. Angew. Chem. Int. Ed. 2012, 51, 1182.
26. Yamamoto, G.; Oki, M. Bull. Chem. Soc. Jpn., 1983, 56, 2082.
27. Toyota, S.; Yamamori, T.; Makino, T.; Oki, M. Bull. Chem. Soc. Jpn., 2000, 73, 2591.
28. Umeda, R.; Hibi, K.; Tobe, Y. Org. Lett., 2009, 11, 4104.
29. Sun, Z.; Huang, K. W.; Wu J. Org. Lett., 2010, 12, 4690.
30. Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc., 2009, 131, 2796.