Synthesis of Bisanthene-Based Polycyclic Aromatic Hydrocarbons

doi:10.6023/cjoc201501025

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1441-1450.DOI: 10.6023/cjoc201501025 Previous Articles Next Articles

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新型多环芳烃Bisanthene衍生物的合成研究进展

李金玲, 谢宝粘, 彭进

河南工业大学材料科学与工程学院郑州 450001

收稿日期:2015-01-20 修回日期:2015-03-02 发布日期:2015-03-09
通讯作者: 李金玲 E-mail:ljlbest1984@gmail.com
基金资助:
国家自然科学基金(No. 21302043), 河南工业大学科技创新人才培育计划(No. 2013CXRC10)和河南工业大学校高层次人才基金(No. 2012BS051)资助项目.

Synthesis of Bisanthene-Based Polycyclic Aromatic Hydrocarbons

Li Jinling, Xie Baozhan, Peng Jin

School of Material Science & Engineering, Henan University of Technology, Zhengzhou 450001

Received:2015-01-20 Revised:2015-03-02 Published:2015-03-09
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21302043); Plan For Scientific Innovation Talent of Henan University of Technology (No. 2013CXRC10); High-Level talent foundation of Henan University of Technology (No. 2012BS051).

Polycyclic aromatic hydrocarbons (PAHs) with extended π-conjugation play a significant role as novel organic optoelectronic materials. As a family member of PAHs, bisanthene possesses unique properties and features such as small band gap and planar diene structure, which benefits it as a key building block to construct new PAHs by appropriate design and chemical modification. For example, the modifications along with its short-axis and long-axis could not only enlarge its π-conjugated path route, but also improve the solubility and stability. The recent research progress in the synthesis and properties of bisanthene derivatives is summarized, and the future research of this field is prospected.

Key words: polycyclic aromatic hydrocarbons (PAHs), bisanthene, π-conjugation, chemical modification, organic optoelectronic materials

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Li Jinling, Xie Baozhan, Peng Jin. Synthesis of Bisanthene-Based Polycyclic Aromatic Hydrocarbons[J]. Chin. J. Org. Chem., 2015, 35(7): 1441-1450.

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[1] (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme, Berlin, Springer, 1952.(b) Zander, M. Polycyclische Aromaten-Kohlenwasserstoffe und Fullerene, Stuttgart, Teubner, 1995.(c) Clar, E. Polycyclic Hydrocarbons, Vol. I/II, Academic Press, New York, 1964. (d) Clar, E. The Aromatic Sextet, Wiley-VCH, London, 1972. (e) Clar, E.; Schmidt, W. Tetrahedron 1979, 35, 2673. (f) Zander, M. Handbook of Polycyclic Aromatic Hydrocarbons, Marcel Dekker, New York, 1983. (g) Harvey, R. G. In Polycyclic Aromatic Hydrocarbons, Wiley-VCH, Weinheim, 1997.
[2] Stein. S. E.; Brown, R. L. J. Am. Chem. Soc. 1987, 109, 3721.
[3] (a) Ye, H.-Y.; Wen, L.; Li, W.-S. Chin. J. Org. Chem. 2012, 32, 266 (in Chinese).(叶怀英, 李文, 李维实, 有机化学, 2012, 32, 266.)(b) Qu, H.-M.; Jiang, L.-L.; Chen, T; Tang, J.-K. Chin. J. Org. Chem. 2014, 34, 1061 (in Chinese).(曲红梅, 蒋丽丽, 陈涛, 唐建可, 有机化学, 2014, 34, 1061.)
[4] (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.(b) Anthony, J. E. Chem. Rev. 2006, 106, 5028.(c) Murphy, A. R.; Fréchet, J. M. J. Chem. Rev. 2007, 107, 1066. (d) Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718.(e) Luo, J.; Xu, M.; Li, R.; Huang, K.-W.; Jiang, C.; Qi, Q.; Zeng, W.; Zhang, J.; Chi, C.; Wang, P.; Wu, J. J. Am. Chem. Soc. 2014, 136 , 265.
[5] (a) Wang, C. L.; Dong, H. L.; Hu, W. P.; Liu, Y. Q.; Zhu, D. B. Chem. Rev. 2012, 112, 2208.(b) Di, C.; Zhang, F.; Zhu, D. B. Adv. Mater 2013, 25, 313.(c) Thorlet, K. J.; Anthonyl, J. E. Isr. J. Chem. 2014, 54, 642.(d) Wang, H. L.; Zhang, L. S.; Chen, Z. G.; Hu, J. Q.; Li, S. J.; Wang, Z. H.; Liu, J. S.; Wang, X. C. Chem. Soc. Rev. 2014, 43, 5234
[6] (a) Anthony, J. E.; Eaton, D. L.; Parkin, S. R. Org. Lett. 2002, 4, 15.(b) Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452.(c) Kim, D. H.; Lee, D. Y.; Lee, H. S.; Lee, W. H.; Kim, Y. H.; Han, J. I.; Cho, K. Adv. Mater. 2007, 19, 678.(d) Wilson, M. W. B.; Rao, A.; Ehrler, B.; Friends, R. H. Acc. Chem. Res. 2013, 46, 1330.
[7] (a) Ling, M.; Erk, P.; Gomez, M.; Koenemann, M.; Locklin, J.; Bao, Z. Adv. Mater. 2007, 19, 1123.(b) Weitz, R. T.; Amsharov, K.; Zschieschang, U.; Villas, E. B.; Goswami, D. K.; Burghard, M.; Dosch, H.; Jansen, M.; Kern, K.; Klauk, H. J. Am. Chem. Soc. 2008, 130, 4637.(c) Piliego, C.; Jarzab, D.; Gigli, G.; Chen, Z.; Facchetti, A.; Loi, M. A. Adv. Mater. 2009, 21, 1573.(d) Liu, C. M.; Xiao, C. Y.; Li, Y.; Hu, W. P.; Li, Z, B.; Wang, Z. H. Chem. Commun. 2014, 50, 12462.
[8] Sun, Z.; Zeng, Z.; Wu, J. Acc. Chem. Res. 2014, 47, 2582.
[9] Kuroda, H. J. Chem. Phys. 1960, 1856.
[10] Clar, E. Chem. Ber. 1948, 81, 52.
[11] Sa?di-Besbes, S.; Grelet, É.; Bock, H. Angew. Chem., Int. Ed. 2006, 45, 1783.
[12] Zhang, K.; Huang, K.-W.; Li, J. L.; Chi, C.; Wu, J. Org. Lett. 2009, 11 ,4854.
[13] Li, J. L.; Zhang, K.; Huang, K.-W.; Chi, C.; Wu, J. J. Org. Chem. 2010, 75, 856.
[14] Kuroda, H. J. Chem. Phys. 1960, 33, 1586.
[15] Arabei, S. M.; Pavich, T. A. J. Appl. Spectrosc. 2000, 67, 23
[16] Hirao, Y.; Konishi, A.; Matsumoto, K.; Kurata, H.; Kubo, T. International Conference of Computational Methods in Sciences and Engineering 2009, Eds.: Simos, T. E.; Maroulis. G., American Institute of Physics, Rhodes, 2012, 1504, pp. 863～866.
[17] Jiang, D.-E.; Sumpter, B. G.; Dai, S. J. Chem. Phys. 2007, 127, 124703.
[18] Jiang, D.-E.; Dai, S. Chem. Phys. Lett. 2008, 466, 72.
[19] Maulding, D. R. J. Org. Chem. 1970, 35, 1221.
[20] Yao, J.; Chi, C.; Wu, J.; Loh, K. Chem. Eur. J. 2009, 15, 9299.
[21] West, R.; Jorgenson, J.; Stearley, K.; Calabrese, J. J. Chem. Soc., Chem. Commun. 1991, 1234.
[22] Takahashi, K.; Suzuki, T.; Akiyama, K.; Ikegami, Y.; Fukazawa, Y. J. Am. Chem. Soc. 1991, 113, 4576.
[23] Takahashi, T.; Matsuoka, K.; Takimiya, K.; Otsubo, T.; Aso, Y. J. Am. Chem. Soc. 2005, 127, 8928.
[24] Dumur, F.; Gautier, N.; Gallego-Planas, N.; Sahin, Y.; Levillain, E.; Mercier, N.; Hudhomme, P.; Masino, M.; Girlando, A.; Lloveras, V.; Vidal-Gancedo, J.; Veciana, J.; Rovira, C. J. Org. Chem. 2004, 69, 2164.
[25] Fort, E. H.; Donovan, P. M.; Scott, L. T. J. Am. Chem. Soc. 2009, 131, 16006.
[26] Fort, E. H.; Scott, L. T. Angew. Chem., Int. Ed. 2010, 49, 6626.
[27] Fort, E. H.; Jeffreys, M. S.; Scott, L. T. Chem. Commun. 2012, 48, 8102.
[28] Fort, E. H.; Scott, L. T. Org. Biomol. Chem. 2012, 10, 5747.
[29] Li, J. L.; Jiao, C. J.; Huang, K.-W.; Wu, J. Chem. Eur. J. 2011, 17,14672.
[30] (a) Clar, E. Nature, London 1948, 161, 238.(b) Clar, E. Chem. Ber. 1949, 82, 55.
[31] Li, J. L.; Chang, J. J.; Tan, P. H. S.; Jiang, H.; Chen, X. D.; Chen, Z. K.; Zhang, J.; Wu, J. Chem. Sci. 2012, 3, 846.
[32] Chang, J.; Li, J.; Chang, K. L.; Zhang, J.; Wu, J. RSC Adv. 2013, 3, 8721.
[33] Dral, P. O.; Kivala, M.; Clark, T. J. Org. Chem. 2013, 78, 1894.
[34] (a) Jiang, W.; Qian, H. L.; Li, Y.; Wang, Z. H. J. Org. Chem. 2008, 73, 7369. (b) Wei, J.; Han, B.; Guo, Q.; Shi, X.; Wang, W.; Wei, N. Angew. Chem., Int. Ed. 2010, 49, 8209. (c) Jiang, W.; Zhou, Y.; Geng, H.; Jiang, S. D.; Yan, S. K.; Hu, W. P.; Wang, Z. H.; Shuai, Z. G.; Pei, J. J. Am. Chem. Soc. 2011, 133, 1.
[35] Service, R. F. Science 2011, 332, 293.

新型多环芳烃Bisanthene衍生物的合成研究进展

Synthesis of Bisanthene-Based Polycyclic Aromatic Hydrocarbons

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