二苯并[a,e]戊搭烯為一種具有獨特梯形且含共軛系統的多環芳香烴化合物，此化合物的骨架是以兩個五員環在中心，兩個六員環在外側。本篇研究中，已成功合成5,10-雙(2-氯苯基)-二苯并[a,e]戊搭烯(2a)、5,10-雙(2,6-二氯苯基)-二苯并[a,e]戊搭烯(2b)、5,10-雙(2-氯萘基)-二苯并[a,e]戊搭烯(2c)、7,14-雙(2-氯苯基)-二萘并[a,e]戊搭烯(2d)、9,18-二苯基-二菲并[a,e]戊搭烯(2e)、9,18-雙(2-氯苯基)-二菲并[a,e]戊搭烯(2f)，其中也嘗試合成9,18-雙(2,6-二氯苯基)-二菲并[a,e]戊搭烯(2g)，但並沒有成功得到，推測為化合物本身立體障礙太大。而本研究除了合成二苯并[a,e]戊搭烯的衍生物外，也嘗試將這些產物進行分子內環化反應，形成類似奈米碳管的次結構，但目前為止僅成功合成雙芴環戊搭烯(23a)，其他的類似結構或許需以其它條件方能得到目標產物。
化合物2a-f、2h、23a和23b經由電化學及光化學實驗，發現以戊搭烯為骨架進行共軛系統延伸時，會造成分子軌域HOMO-LUOM間能隙下降；另外化合物23a、23b及2f結構組成已由單晶X-ray繞射實驗獲得證實。

In this thesis, a series of dibenzo[a,e]pentalene derivatives were synthesized, which are 5,10-bis(2-chlorophenyl)-dibenzo[a,e]pentalene (2a), 5,10-bis(2,6-dichlorophenyl)-dibenzo[a,e]pentalene (2b), 5,10-bis(2-chloronaphthyl)-dibenzo[a,e]pentalene (2c),
7,14-bis(2-chlorophenyl)-dinaphtho[a,e]pentalene (2d), 9,18-diphenyl-diphenanthro-[a,e]pentalene(2e), and 9,18-bis(2-chlorophenyl)-diphenanthro[a,e]pentalene (2f). Synthesis of 9,18-bis(2,6-dichlorophenyl)-diphenanthro[a,e]pentalene (2g) was also attempted, but no desired product was observed in HRMS, which was presumably due to the steric hindrance caused by the structure. In photophysical and electrochemical properties showed the HOMOLUMO energy gaps would decrease if extendedπconjugate system of dibenzo[a,e]pentalenes.This research not only aimed at synthesizing dibenzo[a,e]pentalene derivatives, but also attempted to their intramolecular cyclization, and the resulting structures were similar to the fragmented carbon nanotube structures. Difluorenopentalene (23a) was the only one been successfully synthesized, which was similar to fragmented carbon nanotube structures.

1. Brand, K. Ber. Dtsch. Chem. Ges. 1912, 45, 3071.
2. Zhao, J.; Oniwa, K.; Asao, N.; Yamamoto, Y.; Jin, T.
J. Am. Chem. Soc. 2013, 135, 10222.
3. Chase, D. T.; Fix, A. G.; Kang, S. J.; Rose, B. D.;
Weber, C. D.; Zhong, Y.; Zakharov, L. N.; Lonergan,
M. C.; Nuckolls, C.; Haley, M. M. J. Am. Chem. Soc.
2012,
134, 10349.
4. Ballester, M.; Castañer, J.; Riera, J.; Armet, O. J.
Org. Chem. 1986, 51, 1100.
5. Anderson, M. R.; Brown, R. F. C.; Coulston, K.J.;
Eastwood, F.W.; Ward, A. Aust. J. Chem. 1990, 43,
1137.
6. Müller, V. E.; Munk, K.; Ziemek, P.; Sauerbier, M.
Liebigs Ann. Chem. 1968, 713, 40.
7. Kawase, T.; Konishi, A.; Hirao, Y.; Matsumoto, K.;
Kurata, H.; Kubo, T. Chem. - Eur. J. 2009, 15, 2653.
8. Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc. 2009,
131, 2796.
9. Hashmi, A. S. K.; Wieteck, M.; Braun, I.; Nösel, P.;
Jongbloed, L.; Rudolph, M.; Rominger, F. Adv. Synth.
Catal. 2012, 354, 555.
10. Kroto, H. W.; Heath, J. R.; O’Brien, S. C.; Curl, R.
F.; Smalley, R. E. Nature 1985, 318, 162
11. Iijima, S. Nature 1991, 354, 56.
12. Iijima, S.; Ichihashi, T. Nature 1993, 363, 603.
13. Bethune, D. S.; Klang, C. H.; de Vries, M. S.;
Gorman, G.; Savoy, R.; Vazquez, J.; Beyers, R. Nature
1993, 363, 605.
14. Xiao, L.; Takada, H.; Gan, X.; Miwa, N. Bioorg. Med.
Chem. Lett. 2006, 16, 1590.
15. Ebbesen, T. W.; Takaada, T. Carbon 1995, 33, 973.
16. (a) Dinadayalane, T. C.; Murray, J. C.; Concha, M.
C.; Politzer, P.; Leszczynski, J. J. Chem. Theory
Comput. 2010, 6, 1351. (b) Bettinger, H. F. J. Phys.
Chem. B 2005, 109, 6922. (c) Murray, J. S.; Shields,
Z. P.-I.; Lane, P.; Macaveiu, L.; Bulat, F. A. J.
Mol. Model. 2013, 19, 2825.
17. Orlikowski, D.; Nardelli, M, B.; Bernholc, J.;
Roland, C. Phys. Rev. Lett. 1999, 83, 4132.
18. Lusk, M.-T.; Wu, D.-T.; Carr, L.D. Phys. Rev. B.
2010, 81,155444.
19. 吳遵承博士論文：國立成功大學 民國一百零一年十月
20. Shen, J.; Yuan, D.; Qiao, Y.; Shen, X.; Zhang, Z.;
Zhong, Y.; Yi, Y.; Zhu, X. Org. Lett. 2014, 16, 4924.
21. Krygowski, T. M.; Ejsmont, K.; Stepień, B. T.;
Cyrański, M. K.; Poater, J.; Sola, M. J. Org. Chem.
2004, 69, 6634.
22. Stępień, B. T.; Krygowski, T. M.; Cyrański, M. K.;
Młochowski. J.; Orioli, P.; Abbate, F. ARKIVOC. 2004,
3, 185.
23. Kuang, C.; Yang, Q.; Senbokuc, H.; Tokudac, M.
Tetrahedron 2005, 61, 4043.
24. Peng, C.; Wang, Y.; Liu, L.; Wang, H.; Zhao, J.; Zhu,
Q. Eur. J. Org. Chem. 2010, 818.
25. Musso, D. L.; Clarke, M. J.; Kelley, J. L.; Boswell,
G. E.;Chen, G. Org. Biomol. Chem. 2003, 1, 498.
26. Singh, P. P.; Thatikonda, T.; Kumar, K. A. A.;
Sawant, S. D.; Singh, B.; Sharma, A. K.; Sharma, P.
R.; Singh, D.; Vishwakarma, R. A. J. Org. Chem. 2012,
77, 5823.
27. Charmant, J. P. H.; Fallis, I. A.; Hunt, N. J.;
Lloyd-Jones, G. C.; Murray, M.; Nowak, T. J. Chem.
Soc., Dalton Trans. 2000, 1723.
28. Li, J.; Zhang, J.; Tan, H.; Wang, D.- Z. Org. Lett.
2015, 17, 2522.
29. Carreñ , M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M.
A.; Urbano, A. Synlett. 1997, 1241.
30. Mangas-Sanchez, J.; Busto, E.; Gotor- Fernández, V.;
Gotor, V. Org. Lett. 2010, 12, 3498.
31. Weimar, M.; Correa da Costa, R.; Lee, F.-H.; Fuchter,
M. J. Org. Lett. 2013, 15, 1706.
32. Ma, Y.; Song, C.; Jiang, W.; Wu, Q.; Wang, Y.; Liu,
X.; Andrus, M. B. Org. Lett. 2003, 5, 3317.
33. Dolbier, W. R.; Palmer, K. W. J. Org. Chem. 1993, 58,
7064.
34. Hee Sung Material Co., LTD., Patent: KR2016/51212 A,
2016.