ARTICLE

Synthesis of 1,2,3,4,5-Pentaarylcyclopenta-2,4-diene Derivatives and Their Aggregation-Induced Emission Properties

  • Qiu Shuhai ,
  • Xu Shengjie ,
  • Zhou Guofu ,
  • Shui Lingling ,
  • Zhu Xiaozhang
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  • a Electronic Paper Display Institute, South China Academy of Advanced Optoelectronics, South China Normal University, Guangzhou 510006;
    b CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Received date: 2015-02-26

  Revised date: 2015-03-30

  Online published: 2015-04-03

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 91333113, 21303060), the National Basic Research Program of China (973 Program, No. 2014CB643502), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB12010200), and the Guangdong Natural Science Foundation (No. S2013010014418).

Abstract

Pentaarylated cyclopentcyclodienes have aggregation-induced emission (AIE) characteristics and can be easily derivatized, but are rarely studied. In order to examine the effect of the electronic properties and the position of the substituents on AIE properties, an expedient method for the synthesis of a series of pentaarylated cyclopentadiene derivatives was developed, and their UV-Vis, fluorescence spectra, fluorescence quantum yields as well as the XRD structures of single crystals were investigated. The AIE properties of pentaarylated cyclopentadiene derivatives were studied in detail.

Cite this article

Qiu Shuhai , Xu Shengjie , Zhou Guofu , Shui Lingling , Zhu Xiaozhang . Synthesis of 1,2,3,4,5-Pentaarylcyclopenta-2,4-diene Derivatives and Their Aggregation-Induced Emission Properties[J]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1746 -1753 . DOI: 10.6023/cjoc201502031

References

[1] Luo, J.-D.; Xie, Z.-L.; Lam, J. W. Y.; Cheng, L.; Chen, H.-Y.; Qiu, C.-F.; Kwok, H.-S.; Zhan, X.-W.; Liu, Y.-Q.; Zhu, D.-B.; Tang, B.-Z. Chem. Commun. 2001, 18, 1740.
[2] Mao, W.-G.; Chen, K.; Ouyang, M.; Sun, J.-W.; Zhou, Y.-B.; Wang, Y.-S.; Song, Q.-B.; Zhang, C. Chin. J. Org. Chem. 2014, 34, 161 (in Chinese). (毛文纲, 陈康, 欧阳密, 孙璟玮, 周永兵, 王永胜, 宋庆宝, 张诚, 有机化学, 2014, 34, 161.)
[3] Guan, C.-F.; Qian, Y. Chin. J. Org. Chem. 2014, 34, 537 (in Chinese). (管成飞, 钱鹰, 有机化学, 2014, 34, 537.)
[4] Birks, J. B. Rep. Prog. Phys. 1975, 38, 903.
[5] Hong, Y.-N.; Lam, J. W. Y.; Tang, B.-Z. Chem. Soc. Rev. 2011, 40, 5361.
[6] Mei, J.; Hong, Y.-N.; Lam, J. W. Y.; Qin, A.-J.; Tang, Y.-H.; Tang, B.-Z. Adv. Mater. 2014, 26, 5429.
[7] (a) Zhao, Z.-J.; Chan, C. Y. K.; Chen, S.-M.; Deng, C.-M.; Lam, J. W. Y.; Jim, C. K. W.; Hong, Y.-N.; Lu, P.; Chang, Z.-F.; Chen, X.-P.; Lu, P.; Kwok, H.-S.; Qiu, H.-Y.; Tang, B.-Z. J. Mater. Chem. 2012, 22, 4527. (b) Huang, J.; Yang, X.; Wang, J.-Y.; Zhong, C.; Wang, L.; Qin, J.-G.; Li, Z. J. Mater. Chem. 2012, 22, 2478.
[8] (a) Mei, J.; Tong, J.-Q.; Wang, J.; Qin, A.-J.; Sun, J.-Z.; Tang, B.-Z. J. Mater. Chem. 2012, 22, 17063. (b) Mei, J.; Wang, Y.-J.; Tong, J.-Q.; Wang, J.; Qin, A.-J.; Sun, J.-Z.; Tang, B.-Z. Chem. Eur. J. 2013, 19, 612. (c) Anariba, F.; Chng, L. L.; Abdullah, N. S.; Tay, F. E. H. J. Mater. Chem. 2012, 22, 19303. (d) Yu, Y.; Feng, C.; Hong, Y.-N.; Liu, J.-Z.; Chen, S.-J.; Ng, K. M.; Luo, K.-Q.; Tang, B.-Z. Adv. Mater. 2011, 23, 3298.
[9] Li, H.-Y.; Zhang, X.-Q.; Zhang, X.-Y.; Yang, B.; Wei, Y. Colloids Surf., B 2014, 121, 347.
[10] Chen, X.-J.; Shen, X.-Y.; Guan, E.-J.; Liu, Y.; Qin, A.-J.; Sun, J.-Z.; Tang, B.-Z. Chem. Commun. 2013, 49, 1503.
[11] (a) Franklin, A.; Chng, L.-L.; Nur, S. A.; Francis, T. J. Mater. Chem. 2012, 22, 19303. (b) Tong, H.; Hong, Y.; Dong, Y.; Haeussler, M.; Li, Z.; Lam, J. W. Y.; Dong, Y.; Sung, H. H. Y.; Williams, I. D.; Tang, B.-Z. J. Phys. Chem. B. 2007, 111, 11817.
[12] Chen, L.; Jiang, Y.-B.; Nie, H.; Lu, P.; Sung, H.-H. Y.; Williams, I. D.; Kwok, H.-S.; Huang, F.; Qin, A.-J.; Zhao, Z.-J.; Tang, B.-Z. Adv. Funct. Mater. 2014, 24, 3621.
[13] (a) Wang, M.; Zhang, D.-Q.; Zhang, G.-X.; Zhu, D.-B. Chem. Commun. 2008, 37, 4469. (b) Huang, J.; Wang, M.; Zhou, Y.-Y.; Weng, X.-C.; Shuai, L.; Zhou, X.; Zhang, D.-Q. Bioorg. Med. Chem. 2009, 17, 7743. (c) Liu, Z.-T.; Xue, W.-X.; Cai, Z.-X.; Zhang, G.-X.; Zhang, D.-Q. J. Mater. Chem. 2011, 21, 14487.
[14] Tang, B.-Z.; Zhan, X.-W.; Yu, G.; Lee, P. P. S.; Liu, Y.-Q.; Zhu, D.-B. J. Mater. Chem. 2001, 11, 2974.
[15] Yu, G.; Yin, S.-W.; Liu, Y.-Q.; Chen, J.-S.; Xu, X.-J.; Sun, X.-B.; Ma, D.-G.; Zhan, X.-W.; Peng, Q.; Shuai, Z.-G.; Tang, B.-Z.; Zhu, D.-B.; Fang, W.-H.; Luo, Y. J. Am. Chem. Soc. 2005, 127, 6335.
[16] (a) Zhang, X.-D.; Ye, J.-W.; Xu, L.-F.; Yang, L.-J.; Deng, D.; Ning, G.-L. J. Lumin. 2013, 139, 28. (b) Gu, X.-G.; Yao, J.-J.; Zhang, G.-X.; Yan, Y.-L.; Zhang, C.; Peng, Q.; Liao, Q.; Wu, Y.-S.; Xu, Z.-Z.; Zhao, Y.-S.; Fu, H.-B.; Zhang, D.-Q. Adv. Funct. Mater. 2012, 22, 4862. (c) Wu, Y.-T.; Kuo, M.-Y.; Chang, Y.-T.; Shin, C.-C.; Wu, T.-C.; Tai, C.-C.; Cheng, T.-H.; Liu, W.-S. Angew. Chem., Int. Ed. 2008, 47, 9891. (d) Chen, Z.; Zhang, J.; Song, M.; Yin, J.; Yu, G.-A.; Liu, S.-H. Chem. Commun. 2015, 51, 326.
[17] Anariba, F.; Chng, L. L.; Abdullah, N. S.; Tay, F. E. H. J. Mater. Chem. 2012, 22, 19303.
[18] Dyker, G.; Heiermann, J.; Miura, M.; Inoh, J. I.; Pivsa-Art, S.; Satoh, T.; Nomura, M. Chem.-Eur J. 2000, 18, 3426.
[19] Kanthak, M.; Muth, E.; Dyker, G. Eur. J. Org. Chem. 2010, 31, 6084.
[20] (a) Feng, X.-A.; Tong, B.; Shen, J.-B.; Shi, J.-B.; Han, T.-Y.; Chen, L.; Zhi, J.-G.; Lu, P.; Ma, Y.-G.; Dong, Y.-P. J. Phys. Chem. B 2010, 114, 16731. (b) Ouyang, M.; Yu, C.-H.; Zhang, Y.-J.; Hu, B.; Lu, X.-J.; Sun, J.-W.; Zhang, C. Acta. Phys.-Chim. Sin. 2012, 28, 2944 (in Chinese). (欧阳密, 俞春辉, 张玉建, 胡彬, 吕晓静, 孙璟玮, 张诚, 物理化学学报, 2012, 28, 2944.) (c) Tang, H.-Y.; Zeng, Y.; Li, Y.-Y.; Chen, J.-P.; Li, Y. Acta Chim. Sinica 2011, 69, 2241 (in Chinese). (唐海云, 曾毅, 李迎迎, 陈金平, 李嫕, 化学学报, 2011, 6, 2241.)
[21] Yan, D.-P.; Yang, H.-J.; Meng, Q.-Y.; Lin, H.-Y.; Wei, M. Adv Funct. Mater. 2014, 24, 587.
[22] Chi, Z.-G.; Zhang, X.-Q.; Xu, B.-J.; Zhou, X.; Ma, C. P.; Zhang, Y.; Liu, S.-W.; Xu, J.-R. Chem. Soc. Rev. 2012, 41, 3878.
[23] Dong, Y.-J.; Xu, B.; Zhang, J.-B.; Tan, X.; Wang, L.-J.; Chen, J.-L.; Lv, H.-G.; Wen, S.-P.; Li, B.; Ye, L.; Zou, B.; Tian, W.-J. Angew. Chem., Int. Ed. 2012, 51, 10782.
[24] Cai, R.-R.; Huang, M.-M.; Cui, X.-L.; Zhang, J.-Y.; Du, C.-X.; Wu, Y.-S.; Wu, Y. J. RSC Adv. 2013, 3, 13140.
[25] Chen, X.-P.; Li, X.-H.; Wang, N.-N.; Jin, J.-S.; Lu, P.; Wang, Y.-G. Eur. J. Org. Chem. 2012, 4380.

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