五芳基取代环戊二烯衍生物的合成及其聚集诱导荧光性质研究

doi:10.6023/cjoc201502031

有机化学 ›› 2015, Vol. 35 ›› Issue (8): 1746-1753.DOI: 10.6023/cjoc201502031 上一篇下一篇

研究论文

五芳基取代环戊二烯衍生物的合成及其聚集诱导荧光性质研究

邱淑海^a,b, 许胜杰^b, 周国富^a, 水玲玲^a, 朱晓张^b

a 华南师范大学华南先进光电子研究院彩色电子纸显示技术研究所广州 510006;
b 中国科学院化学研究所有机固体院重点实验室北京 100190

收稿日期:2015-02-26 修回日期:2015-03-30 发布日期:2015-04-03
通讯作者: 水玲玲, 朱晓张 E-mail:shuill@scnu.edu.cn;xzzhu@iccas.ac.cn
基金资助:
国家自然科学基金(Nos. 91333113, 21303060)、国家重点基础研究发展计划(973计划, No. 2014CB643502)、中国科学院先导B专项(No. XDB12010200)、广东省自然科学基金(No. S2013010014418)资助项目.

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

Qiu Shuhai^a,b, Xu Shengjie^b, Zhou Guofu^a, Shui Lingling^a, Zhu Xiaozhang^b

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:2015-02-26 Revised:2015-03-30 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).

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摘要/Abstract

五芳基取代环戊二烯衍生物是一类具有聚集诱导荧光性质的化合物, 但相应的研究比较少. 为了研究不同推拉电子能力的取代基以及取代位置对聚集诱导荧光性质的影响和拓展其在化学传感器、生物探针等方面的应用, 我们合成了不同芳香取代基的五芳基取代环戊二烯及其衍生物, 并对其进行了紫外吸收、荧光光谱、荧光量子产率、单晶分析等方面的测试表征, 重点研究了其聚集诱导荧光性质.

关键词: 五芳基取代环戊二烯, 聚集诱导荧光

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.

Key words: pentaarylated cyclopentadienes, aggregation-induced emission

引用此文

邱淑海, 许胜杰, 周国富, 水玲玲, 朱晓张. 五芳基取代环戊二烯衍生物的合成及其聚集诱导荧光性质研究[J]. 有机化学, 2015, 35(8): 1746-1753.

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]. Chin. J. Org. Chem., 2015, 35(8): 1746-1753.

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[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.

五芳基取代环戊二烯衍生物的合成及其聚集诱导荧光性质研究

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

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