New Progress of Researches in Fluorene Compounds

doi:10.6023/cjoc201204021

Abstract

Fluorene and its derivatives are important compounds, which have biphenyl structure with rigid plane,as well as large π-conjugated system. These special structures of fluorene compounds endow their distinct various functions, properties and biological activities, as well as wide potential application in photoelectrical materials, medicinal agents and so on. More importantly, the fluorene compounds are easily modified and various functional groups could be conveniently introduced into the fluorene ring. The syntheses of fluorene derivatives and their potential applications were extensively investigated and have been become highly active highlight in recent years, and the progress is quite rapid. Combining with our researches and referring other works from literatures, this paper systematically reviews the recent advance in the research and development of fluorene in organic electro-luminescence materials, two-photon absorbing materials, photochromic materials, solar cells, medicinal chemistry and so on. The perspectives of the foreseeable future are also presented.

Key words: fluorene, organic light emitting materials, solar cell, two-photon absorption, photochromic, biosensor

Cite this article

Huo Yanping, Fang Xiaoming, Huang Baohua, Zhang Kun, NIE Xiaoli, Zeng Heping. New Progress of Researches in Fluorene Compounds[J]. Chin. J. Org. Chem., 2012, 32(07): 1169-1185.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Schluter, A. D. J. Polym. Sci. Part A: Polym Chem., 2001, 39, 1533(b)Zhong, H.L.; Lai, H.; Fang, Q. J. Phys. Chem. C. 2011, 115, 2423.(c)Sun, J.; Lai, H.; Zhong, H.L.; Fang, Q. Thin Solid Films, 2011, 519, 7772.

[2] Stork, M.; Gaylord, B. S.; Heeger, A.J.; Bazan, G.C. Adv. Mater, 2002, 14, 3613
[3] Svensson, M.; Zhang, F. L.; Veenstra,S. C. Adv. Mater. 2003, 15(12), 988
[4] Cliferson, T.; Aurore, L.; Kevin B. Macromolecules 2011, 44, 4012.

[5] Pei, J.; Liu, X. L.; Huang,W. Macromolecules, 2003, 36: 323.
[6] Liu, B.; Yu, W. L.; Huang, W. Macromolecules, 2002, 35: 4975.
[7] Anthony, J. E. Chem. Rev. 2006, 106, 5028.

[8] Okamoto, T.; Bao, Z. J. Am. Chem. Soc. 2007, 129, 10308
[9] Snaith, H. J.; Greenham, N. C.; Friend, R. H. Adv. Mater. 2004, 16, 1640.

[10] Werts, M. H.W.; Gmouh, S.; Mongin, O.; Pons, T.; Desce, M. J. Am. Chem. Soc. 2004, 126 (50): 16294
[11] Zhou, X.H ; Yan, J.C; Pei, J. Macromolecules, 2004, 37, 7078.

[12] List, E. J.W.; Guentner, R.; Scherf, U. Adv. Mater, 2002, 14, 374.

[13] (a) Kraft, A.; Grimsdate, A. C.; Homes, A. B. Angew. Chem. Int. Ed. 1998, 37, 402 [b] Goel, A.; Chaurasia, S.; Kumar, V.; Manoharan, S.; Anand, R. S. CN 102046598 A, 2009 [Chem. Abstr. 2009, 151, 458971]
[14] Andrew, C.; Grimsdale ; Khai, L. C.; Rainer, E.M.; Pawel, G. J. Andrew B. H.Chem.Rev. 2009, 109, 897.

[15] Zhang, L.; Lin, Z.Q.; Gu; J. F.; Huang,W. Acta. Phys. Chim.Sin. 2010, 26(7),1934 (in Chinese).(张龙,林宗琼,顾菊芳,黄维. 物理化学学报,2010, 26(7), 1934
[16] Jiang, Z. Q.; Liu, Z. Y.; Yang,C. L.; Zhong, C.; Qin, J.G.; Yu, G.; Liu, Y. Q. Adv.Funct. Mater. 2009, 19, 3987.

[17] Zhen, C. G.; Chen, Z. K.; Liu, Q.D.; Dai, Y. F.; Shin, R.Y. C.; Chang,S.Y.; Kieffer, J. Adv. Mater. 2009, 21, 2425.

[18] Liu, B.; Yu, W.L.; Lai, Y.H.; Huang, W.; Chem. Commun, 2000, 551.
[19] Guo, J.G.; Cui, Y. M.; Lin, H. X.; Xie, X. Z.; Chen, H.F. J. Photochem Photobio. A:Chemistry. 2011, 219, 42.

[20] Huang, C. W.; Tsai, C. L.; Liu, C. Y.; Jen, T. H.; Yang, N. J.; Chen, S. A. Macromolecules, 2012, 45, 1281.

[21] Deng, J.Y.; Liu,Y.; Wang, Y. F.; Tan, H.; Zhang, Z.Y; Lei,G. T.; Yu, J.T.; Zhu, M. X.; Zhu,W. G.; Cao, Y. European Ploymer Journal, 2011, 47, 1836.

[22] Yildirim, M.; Kaya, I. Synth. Met. 2011, 161, 13.

[23] Xiao, L. X. ; Hu, S.Y.; Kong, S.; Chen, Z..J; Qu,B.; Gong, Q.H. Acta Phys.-Chim.Sin. 2011, 27(4), 977 (in Chinese).(肖立新,胡双元,孔胜,陈志坚,曲波,龚旗煌,物理化学学报,2011, 27(4), 977)
[24] Wang, K. L.; Leung, M.K.; Hsieh, L.G.; Chang, C.C.; Lee, K. R.; Wu, C.L. ; Jiang, J.C. ; Tseng, C. Y.; Wang, H.T. Organic Electronics, 2011, 12,1048.

[25] Jiang, H. J.; Huang, W. Progress in Chemistry. 2008, 20(4), 539 (in Chinese).(姜鸿基,黄维,化学进展,2008, 20(4), 539)
[26] Luo, J.; Li, X. Z.; Chen, J. W.; Huang, F.; Cao, Y. Synth. Met. 2011, 161, 1982.

[27] Wang, L. X.; Jing, X.B.; Wang, F. S. Acta Polymerica Sinica, 2009, 10, 980(in Chinese ).(王利祥,景遐斌,王佛松,高分子学报,2009, 10, 980)
[28 ] Tu, G. L.; Mei, C. Y.; Zhou, Q. G.; Cheng, Y. X; Wang, L. X.; Ma, D.G., Jing, X.B.; Wang, F. S. Adv. Funct. Mater. 2006, 16, 101.

[29] Zhang, Y.; Hou, Q.; Zheng, S. W.; Li, S. T.; Fan, G, H.Journal Of South China Normal University, 2009, 4, 57.(章勇,侯琼,郑树文,李述体, 范广涵,华南师范大学学报,2009, 4, 57.)
[30] Ho, J. S.; Lee, S.M.; Lee, J.Y.; Choi, B. H.; Moon, D. K. Synth. Met. 2011, 161, 2451.

[31] Hsieh, B.Y.; Chen,Y. J Polym Sci, Part A: Polym Chem, 2008, 46, 3703.
[32] Ouyang, X. H; Wang, G. R; Zeng, H. P.; Zhang, W. M.; Li, J. J. Organomet Chem. 2009, 694, 3511.

[33] Wang, T.-T.; Zeng, G.-C.; Zeng, H.-P.; Liu, P.-Y.; Wang, R.-X.; Zhang, Z.-J.; Xiong, Y.-L. Tetrahedron 2009, 65, 6325.

[34] Zeng, H.-P.; Wang, G.-R.; Zeng, G.-C.; Li, J. Dyes Pigm. 2009, 83,155.

[35] Yuen, M. Y.; Kui, S. C. F.; Low, K. H.; Kwok, C. C.; Chui, S. S.Y.; Ma, C. W.; Zhu, N. Y.; Che, C. M. Chem. Eur. J. 2010, 16, 14131.
[36 ] Ahmed, S. A. M.; Al-Raqa, S.Y. J. Phys. Org. Chem. 2011, 24, 173.

[37] Ahmed, S. A. M. Tetrahedron Lett. 2010, 51, 730.

[38] Ahmed, S. A. M. Tetrahedron. 2009, 65, 1373.

[39] Li, C. H. ; Zheng, C. M.; Zeng, H. P. Chin. J. Org. Chem. 2011, 5, 659 (in Chinese).(李财花,郑春梅,曾和平,有机化学,2011, 5, 659)
[40] Marco, S.; Andres, J. J. Am. Chem. Soc, 2010, 132, 8372.

[41] Dürr, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 413.

[42] Miller, M. J.; Wei, S. H.; Parker, I.; Cahalan, M. D. Science. 2002,296, 1869.

[43] Zhou, W. H.; Kuebler, S. M.; Braun, K. L.; Yu, T. Y.; Cammack, J. K.; Ober, C. K.; Perry, J. W.; Marder, S. R. Science. 2002, 296, 1106.

[44] Parthenopoulos, D. A.; Rentzepis, P. M. Science. 1989, 245, 843.

[45] Bhawalkar, J. D.; Kumar, N. D.; Zhao, C. F.; Prasad, P. N. J. Clin.Laser Med. Surg. 1997, 15, 201.
[46] Perry, J. W.; Mansour, K.; Lee, I. Y. S.; Wu, X. L.; Bedworth, P. V.; Chen, C. T.; Ng, D.; Marder, S. R.; Miles, P.; Wada, T.; Tian, M.; Sasabe, H.Science. 1996, 273, 1533.

[47] Thivierge, C.; Loudet, Aurore.; Burgess, Kevin. Macromolecules, 2011, 44, 4012.
[48] Belfield, K. D.; Morales, A. R.; Kang, B. S.; Hales, J. M.; Hagan, D. J.; Van Stryland, E. W.; Chapela, V. M.; Percino. J. Chem. Mater. 2004, 16,4634.

[49] Yao, S.; Belfield, K. D. J. Org. Chem. 2005, 70, 5126.

[50 ] Belfield, K. D.; Yao, S.; Bondar, M. V. Adv. Polym. Sci. 2008, 213, 97.
[51] Yanez, C. O.; Andrade, C. D.; Belfield, K. D. Chem. Commun. 2009, 827.
[52] Moura, G. L. C.; Simas, A. M. J. Phys. Chem. C. 2010, 114, 6106.
[53] Andrade, C. D.; Yanez, C. O.; Rodriguez, L.; Belfield, K. D. J. Org. Chem. 2010, 75, 3975.

[54] Wang, H. L.; Li, Z.; Shao, P.; Qin, J.G.; Huang Z. L. J. Phys. Chem. B. 2010, 114, 22.
[55] Ouyang, X.H.; Huo, Y.P. Appl. Phys. A. 2011, 105, 891
[56] Scherf, U.; List, E. J. W. Adv. Mater. 2002, 14, 477.

[57] Shen,P.; Tang, Y.H ; Jiang, S.H.; Chen, H. J.; Zheng, X.Y.; Wang, X.Y.; Zhao, B.; Tan, S.T. Org. Electron. 2011. 12, 125.
[58] Sahu, D.; Padhy, H.; Patra, D.; Yin, J. F.; Hsu, Y. C.; Lin, J. T.; Lu, K. L.; Wei, K. H.; Lin, H. C. Tetrahedron. 2011, 67, 303.

[59] Liu, B. J.; Hu,W.; Chen, C. H. Polymer, 2004, 45(10), 3241.
[60] Zhang, F. L.; Perzon, E.; Wang, X.J. Adv Funct Mater. 2005, 15 (5),745.
[61] Zhang, F. L.; Mammo, W.; Andersson, L. M..Adv. Mater. 2006, 18, 2169.

[62] Hou, Q.; Zhang, Y.; Li F. Organometallics. 2005, 24, 4509.

[63] Schulz, G. L.; Holdcroft, S. Chem. Mater. 2008, 20, 5351.

[64] Liu, L.; Ho, C. L.; Wong, W. Y.; Cheung, K.Y.; Fung, M. K.; Lam, W. T.; Djurisic, A.B.; Chan, W. K. Adv. Funct. Mater. 2008, 18. 2824.
[65] Wang, S.; Janice W.Hong ; Guillermo C.Bazan. Org.Lett. 2005, 7(10), 1907.
[66] Xing, C. F.; Xu, Q. L.; Tang, H.W.; Liu, L. B.; Wang, S. J. Am. Chem. Soc, 2009, 131, 13117.

[67] Feng, F. F.; He, F.; An, L. L.; Wang, S.; Li, Y. L; Zhu, D. B. Adv. Mater. 2008, 20, 2959.

[68] Feng, X. L.; Yang, G. M.; Liu, L, B.; Yang, Q.; Wang, S; Zhu, D. B. Adv. Mater. 2012, 24, 637.

[69] Feng, F. F.; Tang.Y. L.; He, F.; Yu, M. H.; Duan, X. R.; Wang, S.; Li, Y. L.; Zhu, D. B. Adv.Mater.2007, 3490.
[70] Stork, M.; Gaylord, B. S.; Heeger, A.J.; Bazan, G. C. Adv Mater, 2002, 14, 361.

[71] He, F.; Y. L.; Yu, M. H.; Wang, S.; Li, Y. L.; Zhu, D. B. Adv. Funct Mater, 2006, 16, 91.

[72] Zhou, X. H.; Yan, J. C.; Pei J. Macromolecules, 2004, 37, 7078.

[73] Xing, C. F.; Yu, M. H.; Wang S, Shi, Z.; Li, Y. L.; Zhu, D. B. Macromol Rapid Commun, 2007, 28, 241.

[74] Shao,Y. Journal of Hubei University for Nationalities, 2009, 27(2), 152 (in Chinese ).(邵宇,湖北民族学院学报,2009, 27(2), 152)
[75] Zhang,W.X; Zhang,Y.M ; Wei,T.B. App. Chem. 2008, 25(12): 1460 (in Chinese).(徐维霞, 张有明, 魏太保. 应用化学, 2008, 25(12): 1460)
[76] Zhang, F. L.; Mammo,W.; Andersson, L. M. Adv. Mater. 2006, 18, 2169.

[77] Wang, X. J.; Perzon, E.; Delgado, J. L. Appl. Phys. Let. 2004, 85(21), 5081.
[78] Ding, F. C.; Chen,Q. S.; Lai,S. L.; Li, X.Y. China Plastics, 2011, 25(5), 36 (in Chinese).(丁富传,陈清松,赖寿莲,李晓燕,中国塑料,2011, 25(5), 36)
[79] Luminita Marin ; Elena Perju ; Mariana D.D. European Polymer Journal. 2011, 47,1284.

[80] Han, D.M; Shu,D.; Wang, S.J ; Xiao,M ; Meng,Y.Z. Membrane Science and Technology, 2010,30(1),5 (in Chinese).(韩东梅,舒东,王拴紧,肖敏,孟跃中,膜科学与技术. 2010, 30(1), 55.)
[81] Tian, S.H.; Shu, D.; Meng,Y.Z. Membrane Science and Technology, 2008, 28(2), 18 (in Chinese).(田双红, 舒东, 孟跃中.膜科学与技术, 2008, 28(2), 18.)
[82] Vorcoe, J. R.; Slade, R. C. T. Fuel Cells, 2005, 2, 187.
[83] Xu, T. J. Membr. Sci. 2005, 263, 1.

[84] Tanaka, M.; Koike, M.; Miyatake, K.; Watanabe, M. Macromolecules. 2010, 43, 2657
[85] Tanaka, M.; Koike, M.; Miyatake, K.; Watanabe, M. Polym. Chem. 2011, 2, 99.

[86] Tanaka, M.; Fukasawa, K.; Nishino, E.; Yamaguchi, S.; Yamada,K.; Tanaka, H.; Bae, B.; Miyatake, K.; Watanabe, M. J. Am. Chem. Soc. 2011,133, 10646.

芴类化合物的研究新进展