SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 >Issue 03: 552 - 559

DOI: https://doi.org/10.6023/cjoc1107151

Articles

Synthesis and Properties of 9,9'-Diarylspriofluorene with Substituted Group at 2,7-Position of Fluorene

  • Ouyang Mi ,
  • Yu Zhenwei ,
  • Zhang Yujian ,
  • Xiang Wenqin ,
  • Hu Bin ,
  • Zhang Cheng
Expand
  • International Science and Technology Cooperation Base of Energy Materials and Application, State Key Laboratory Breeding Base for Green Chemistry Synthesis Technology, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014

Received date: 2011-07-15

  Revised date: 2011-10-25

  Online published: 2012-03-24

Supported by

Project supported by the National Basic Research Program of China (Nos. 2010CB635108, 2011CBA00700) and the International Technical Cooperation and Exchanges (No. S2012ZR0152)

Fold

Abstract

A series of novel 2-/2,7-(di)arylfluorene building-blocks were synthesized and utilized to prepare novel organic blue-emitting oligomers via Suzuki reaction and Friedel-Crafts reaction. The desired oligomers contained the 4-methyltriphenylamine core and fluorene derivatives peripheries. Their structures were confirmed by NMR and MS techniques and elemental analysis. The maximum photoluminescence (PL) emission wavelengths of the compounds ranged from 442 to 466 nm. Cyclic voltammetry (CV) showed that the highest occupied molecular orbital (HOMO) energy level of the compounds was located between －5.15 and －5.19 eV. The results of differential scanning calorimeter (DSC) and thermogravimetric (TG) indicated that these materials had excellent thermal stability with glass transition temperature of higher than 166 ℃ and thermal-decomposition temperature over 398 ℃.

Key words： 9,9’-diarylspirofluorene; Suzuki reaction; Friedel-Crafts reaction; thermal stability

Cite this article

Ouyang Mi , Yu Zhenwei , Zhang Yujian , Xiang Wenqin , Hu Bin , Zhang Cheng . Synthesis and Properties of 9,9'-Diarylspriofluorene with Substituted Group at 2,7-Position of Fluorene[J]. Chinese Journal of Organic Chemistry, 2012 , (03) : 552 -559 . DOI: 10.6023/cjoc1107151

References

[1] Wei, R.-B.; Liu, Y.; Guo, J.-J.; Liu, B.; Zhang, D.-W. Chin. J. Org.Chem. 2008, 28, 390 (in Chinese).(魏荣宝, 刘洋, 郭金晶, 刘博, 张大为, 有机化学, 2008, 28,390.)

[2] Mao, B.-X.; Zhang, D.-P.; Hua, X.-Y.; Jiang, H.-J.; Chen, R.-F.;Deng, X.-Y. Prog. Chem. 2010, 22, 2353 (in Chinese).(毛炳雪, 张大鹏, 华晓阳, 姜鸿基, 陈润锋, 邓先宇, 化学进展,2010, 22, 2353.)

[3] Shen, J. Y.; Lee, C. Y.; Huang, T. H.; Lin, J. T.; Tao, Y. T.; Tsai,C. J. Mater. Chem. 2005, 15, 2455.  

[4] Chi, C. C.; Chiang, C. L.; Liu, S. W.; Yueh, H.; Chen, C. T.; Chen,C. T. J. Mater. Chem. 2009, 19, 5561.  

[5] Spehr, T.; Pudzich, R.; Fuhrmann, T.; Salbeck, J. Org. Electron.2003, 4, 61.  

[6] Wong, K. T.; Liao, Y. L.; Lin, Y. T.; Su, H. C.; Wu, C. Org. Lett.2005, 7, 5131.  

[7] Cho, N.; Choi, H.; Kim, D.; Song, K.; Kang, M. S.; Kang, S. O.;Ko, J. Tetrahedron 2009, 65, 6236.  

[8] Heredia, D.; Natera, J.; Gervaldo, M.; Otero, L.; Fungo, F.; Lin, C.Y.; Wong, K. T. Org. Lett. 2010, 12, 12.  

[9] Li, C.-H.; Zheng, C.-M.; Zeng, H.-P. Chin. J. Org. Chem. 2001, 31,659 (in Chinese).(李财花, 郑春梅, 曾和平, 有机化学, 2011, 31, 659.)

[10] Chiang, C. L.; Shu, C. F.; Chen, C. T. Org. Lett. 2005, 7, 3717.  

[11] Shen, W. J.; Dodda, R.; Wu, C. C.; Wu, F. I.; Liu, T. H.; Chen, H.H.; Chen, C. H.; Shu, C. F. Chem. Mater. 2004, 16, 930.  

[12] Chun, C.; Kim, M. J.; Vak, D.; Kim, D. Y. J. Mater. Chem. 2003,13, 2904.  

[13] Ye, S.; Liu, Y.; Di, C.; Xi, H.; Wu, W.; Wen, Y.; Lu, K.; Du, Y.;Di, C.; Liu, Y.; Yu, G. Chem. Mater. 2009, 21, 1333.  

[14] McFarlane, S. L.; Coumont, L. S.; Poercey, D. G.; McDonald, R.;Veinot, J. G. C. Macromolecules 2008, 41, 7780.  

[15] Wong, K. T.; Chen, R. T.; Fang, F. C.; Wu, C.; Lin, Y. T. Org. Lett.2005, 7, 1979.  

[16] Huo, Y. P.; Zhu, S. Z.; Hu, S. Tetrahedron 2010, 66, 8635.  

[17] Setayesh, S.; Grimsdale, A. C.; Well, T.; Enkelmann, V.; Müllen,K.; Meghdadi, F.; List, E. J. W.; Leising, G. J. Am. Chem. Soc.2001, 123, 946.  

[18] Wu, C.; Liu, T. L.; Hung, W. Y.; Lin, Y. T.; Wong, K. T.; Chen, R.T.; Chen, Y. M.; Chien, Y. Y. J. Am. Chem. Soc. 2003, 125, 3710.  

[19] Wu, F. I.; Reddy, S.; Shu, C. F. Chem. Mater. 2003, 15, 269.  

[20] Chao, T. C.; Lin, Y. T.; Yang, C. Y.; Hung, T. S.; Chou, H. C.; Wu,C. C.; Wong, K. T. Adv. Mater. 2005, 17, 992.  

[21] Tao, S.; Peng, Z.; Zhang, X.; Wang, P.; Lee, C. S.; Lee, S. T. Adv.Funct. Mater. 2005, 15, 1716.  

[22] Omer, K. M.; Ku, S. Y.; Wong, K. T.; Bard, A. J. J. Am. Chem.Soc. 2009, 131, 10733.  

[23] Wu, W. C.; Lee, W. Y.; Chen, W. C. Macromol. Chem. Phys. 2006,207, 1131.  

[24] Lee, W. Y.; Cheng, K. F.; Wang, T. F.; Chen, W. C.; Tsai, F. Y.Thin Solid Films 2010, 518, 2119.  

[25] Shao, K. F.; Li, Y. F.; Yang, L. M.; Xu, X. J.; Yu, G.; Liu, Y. Q.Chem. Lett. 2005, 134, 1604.

[26] Ko, C. W.; Tao, Y. T. Synth. Met. 2002, 126, 37.  

[27] Zhang, C.; Zhang, Y. J.; Xiang, W. Q.; Hu, B.; Ouyang, M.; Ma, C.Chem. Lett. 2010, 39, 520.  

[28] Hou, X. Y.; Li, T. C.; Yin, C. R.; Xu, H.; Lin, J.; Hua, Y. R.; Chen,D. Y.; Xie, L. H.; Huang, W. Synth. Met. 2009, 159, 1055.  

[29] Leeuw, D. M.; Simenon, M. M. J.; Brown, A. R.; Einerhand, R. E.F. Synth. Met. 1997, 87, 53.  

[30] Liao, Y. L.; Lin, C. Y.; Wong, K. T.; Hou, T. H.; Hung, W. Y. Org.Lett. 2007, 9, 4511.  

[31] Li, Y.; Ding, J.; Day, M.; Tao, Y.; Lu, J.; D'iorio, M. Chem. Mater.2004, 16, 2165.  

[32] Wong, K. T.; Ku, S. Y.; Cheng, Y. M.; Lin, X. Y.; Hung, Y. Y.; Pu,S. C.; Chou, P. T.; Lee, G. H.; Peng, S. M. J. Org. Chem. 2006, 71,456.  
Options
Outlines

/

〈 〉