荧蒽修饰的四苯基乙烯衍生物:分子合成、聚集增强荧光特性及其对苦味酸的高灵敏度检测

doi:10.6023/A16080410

化学学报 ›› 2016, Vol. 74 ›› Issue (11): 893-901.DOI: 10.6023/A16080410 上一篇下一篇

研究论文

荧蒽修饰的四苯基乙烯衍生物:分子合成、聚集增强荧光特性及其对苦味酸的高灵敏度检测

白玮^a, 史杨^a, 宋忱^a, 贺杰^a, 秦安军^b, 孙景志^a, 唐本忠^a,b,c

a 浙江大学高分子合成与功能构造教育部重点实验室高分子科学与工程学系杭州 310027;
b 华南理工大学发光材料与器件国家重点实验室广州 510640;
c 香港科技大学化学系香港九龙清水湾

投稿日期:2016-08-14 发布日期:2016-10-20
通讯作者: 孙景志, 唐本忠 E-mail:sunjz@zju.edu.cn;tangbenz@ust.hk
基金资助:
项目受国家自然科学基金（No.51273175）、国家重点基础研究发展计划（973项目，No.2012CB834704）资助.

Fluoranthene-Modified Tetraphenylethene Derivatives: Synthesis, Aggregation-Enhanced Emission Characteristic and Their Highly Sensitive Detection of Picric Acid

Bai Wei^a, Shi Yang^a, Song Chen^a, He Jie^a, Qin Anjun^b, Sun Jing Zhi^a, Tang Ben Zhong^a,b,c

a MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027;
b Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640;
c Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Institute for Advanced Study, Division of Biomedical Engineering, Division of Life Science, State Key Laboratory of Molecular Neuroscience and Institute of Molecular Functional Materials, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong

Received:2016-08-14 Published:2016-10-20
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51273175), and National Basic Research Program of China (973 Program, No. 2012CB834704).

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1. 荧蒽修饰的四苯基乙烯衍生物:分子合成、聚集增强荧光特性及其对苦味酸的高灵敏度检测.PDF(903KB)

摘要/Abstract

由于聚集体和固态发光量子效率高等优点，因此聚集诱导发光（AIE）材料成为光电功能材料研究领域的热点，拓展AIE分子体系始终是这一领域中的关键和基础的科学问题.通过Suzuki-Miyaura偶联这一条件较为温和的反应，将AIE生色团四苯基乙烯（TPE）与荧蒽直接共轭键接，制备得到单荧蒽和双荧蒽修饰的TPE衍生物TPE-FA与TPE-DFA，它们具有聚集增强荧光（AEE）行为，聚集体发射峰值波长分别在477和494 nm，固体薄膜的绝对荧光量子产率高达74.1%和40.4%.它们可以高灵敏地检测苦味酸，荧光猝灭常数大，检出限低于1 μg·g^-1.这两种AEE分子可望用于其它多硝基取代的芳香类吸电子分子的检测.

关键词: 四苯基乙烯, 荧蒽, 聚集诱导发光(AIE), 聚集增强荧光(AEE), 苦味酸

Aggregation-induced emission (AIE) active compounds and materials have become one of the hottest research topics worldwide, due to their unprecedented merits such as ultra-high fluorescence quantum efficiencies as aggregates or in solid state. Up to now, it is still extremely crucial and fundamental to expand the AIE-genic molecular systems for this research area. Here, we prepared two fluoranthene-modified tetraphenylethene (TPE) derivatives, TPE-FA and TPE-DFA, through the Suzuki-Miyaura coupling between boronate-bearing TPE and bromo-bearing fluoranthene under mild reaction condition. The conjugation between fluoranthene and TPE moieties assures that the as-prepared TPE-FA and TPE-DFA both possess aggrega-tion-enhanced emission (AEE) characteristics. The emission maximum of TPE-FA and TPE-DFA as aggregates in THF/water mixtures is at 477 nm and 494 nm, and the absolute quantum yields of the two compounds in solid films are as high as 74.1% and 40.4%, respectively. They can be utilized as fluorescent probes for picric acid with high sensitivity. Their quenching coef-ficients can be as high as 4×10⁴ L·mol^-1, while their detection limits can be lower than 1 μg·g^-1. These AEE-active molecules are promising to act as fluorescent probes in the detection of other nitro-substituted electron-deficient molecules.

Key words: tetraphenylethene, fluoranthene, aggregation-induced emission (AIE), aggregation-enhanced emission (AEE), picric acid

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白玮, 史杨, 宋忱, 贺杰, 秦安军, 孙景志, 唐本忠. 荧蒽修饰的四苯基乙烯衍生物:分子合成、聚集增强荧光特性及其对苦味酸的高灵敏度检测[J]. 化学学报, 2016, 74(11): 893-901.

Bai Wei, Shi Yang, Song Chen, He Jie, Qin Anjun, Sun Jing Zhi, Tang Ben Zhong. Fluoranthene-Modified Tetraphenylethene Derivatives: Synthesis, Aggregation-Enhanced Emission Characteristic and Their Highly Sensitive Detection of Picric Acid[J]. Acta Chim. Sinica, 2016, 74(11): 893-901.

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[1] (a) Basabe-Desmonts, L.; Reinhoudt, D. N.; Crego-Calama, M. Chem. Soc. Rev. 2007, 36, 993;
(b) Bao, Y.; Wang, T.; Li, Q.; Du, F.; Bai, R.; Smet, M.; Dehaen, W. Polym. Chem. 2014, 5, 792;
(c) Yuan, L.; Lin, W.; Zheng, K.; He, L.; Huang, W. Chem. Soc. Rev. 2013, 42, 622;
(d) Dias, F. B.; Bourdakos, K. N.; Jankus, V.; Moss, K. C.; Kamtekar, K. T.; Bhalla, V.; Santos, J.; Bryce, M. R.; Monkman, A. P. Adv. Mater. 2013, 25, 3707;
(e) Li, W.; Pan, Y.; Xiao, R.; Peng, Q.; Zhang, S.; Ma, D.; Li, F.; Shen, F.; Wang, Y.; Yang, B.; Ma, Y. Adv. Funct. Mater. 2014, 24, 1609;
(f) Zhang, Q.; Tsang, D.; Kuwabara, H.; Hatae, Y.; Li, B.; Takahashi, T.; Lee, S. Y.; Yasuda, T.; Adachi, C. Adv. Mater. 2015, 27, 2096.
[2] Birks, J. B. Photophysics of Aromatic Molecules, Wiley, London, 1970.
[3] (a) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 37, 1740;
(b) Mei, J.; Hong, Y.; Lam, J. W. Y.; Qin, A.; Tang, Y.; Tang, B. Z. Adv. Mater. 2014, 26, 5429;
(c) Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718;
(d) Wang, H.; Zhao, E.; Lam, J. W. Y.; Tang, B. Z. Mater. Today 2015, 18, 365.
[4] (a) Wang, M.; Zhang, G.; Zhang, D.; Zhu, D.; Tang, B. Z. J. Mater. Chem. 2010, 20, 1858;
(b) Liang, J.; Tang, B. Z.; Liu, B. Chem. Soc. Rev. 2015, 44, 2798;
(c) Zhang, X.; Wang, K.; Liu, M.; Zhang, X.; Tao, L.; Chen, Y.; Wei, Y. Nanoscale 2015, 7, 11486;
(d) Dong, Y. Q.; Lam, J. W. Y.; Tang, B. Z. J. Phys. Chem. Lett. 2015, 6, 3429;
(e) Yang, J.; Huang, J.; Li, Q.; Li, Z. J. Mater. Chem. C 2016, 4, 2663.
[5] (a) Tseng, N.-W.; Liu, J.; Ng, J. C. Y.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Tang, B. Z. Chem. Sci. 2012, 3, 493;
(b) Liang, G.; Lam, J. W. Y.; Qin, W.; Li, J.; Xie, N.; Tang, B. Z. Chem. Commun. 2014, 50, 1725;
(c) Parrot, E. P. J.; Tan, N. Y.; Hu, R.; Zeitler, J. A.; Tang, B. Z.; Pickwell-MacPherson, E. Mater. Horiz. 2014, 1, 251;
(d) Yuan, H.; Wang, K.; Yang, K.; Liu, B.; Zou, B. J. Phys. Chem. Lett. 2014, 5, 2968;
(e) Sun, G.; Zhao, Y.; Liang, W. J. Chem. Theory Comput. 2015, 11, 2257.
[6] (a) Zhao, Z.; Lam, J. W. Y.; Tang, B. Z. J. Mater. Chem. 2012, 22, 23726;
(b) Wang, J.; Mei, J.; Hu, R.; Sun, J. Z.; Qin, A.; Tang, B. Z. J. Am. Chem. Soc. 2012, 134, 9956;
(c) Bai, W.; Wang, Z.; Tong, J.; Mei, J.; Qin, A.; Sun, J. Z.; Tang, B. Z. Chem. Commun. 2015, 51, 1089;
(d) Chen, S.; Hong, Y.; Zeng, Y.; Sun, Q.; Liu, Y.; Zhao, E.; Bai, G.; Qu, J.; Hao, J.; Tang, B. Z. Chem. Eur. J. 2015, 21, 4315;
(e) Wang, C.; Xu, B.; Li, M.; Chi, Z.; Xie, Y.; Li, Q.; Li, Z. Mater. Horiz. 2016, 3, 220.
[7] (a) He, J.; Xu, B.; Chen, F.; Xia, H.; Li, K.; Ye, L.; Tian, W. J. Phys. Chem. C 2009, 113, 9892;
(b) Lu, H.; Xu, B.; Dong, Y.; Chen, F.; Li, Y.; Li, Z.; He, J.; Li, H.; Tian, W. Langmuir 2010, 26, 6838;
(c) Chen, J. L.; Ma, S. Q.; Xu, B.; Zhang, J. B.; Dong, Y. J.; Tian, W. J. Chin. Sci. Bull. 2013, 58, 2747.
[8] (a) Chen, M.; Li, L.; Nie, H.; Tong, J.; Yan, L.; Xu, B.; Sun, J. Z.; Tian, W.; Zhao, Z.; Qin, A.; Tang, B. Z. Chem. Sci. 2015, 6, 1932;
(b) Chen, M.; Li, L.; Nie, H.; Shi, Y.; Mei, J.; Wang, J.; Sun, J. Z.; Qin, A.; Tang, B. Z. Chem. Commun. 2015, 51, 10710;
(c) Pan, L. X.; Luo, W. W.; Chen, M.; Liu, J. K.; Xu, L.; Hu, R. R.; Zhao, Z. J.; Qin, A. J.; Tang, B. Z. Chin. J. Org. Chem. 2016, 36, 1316(in Chinese). (潘凌翔, 罗文文, 陈明, 刘峻恺, 徐露, 胡蓉蓉, 赵祖金, 秦安军, 唐本忠, 有机化学, 2016, 36, 1316.)
[9] (a) Hu, R.; Lam, J. W. Y.; Liu, Y.; Zhang, X.; Tang, B. Z. Chem. Eur. J. 2013, 19, 5617;
(b) Li, L.; Chen, M.; Zhang, H.; Nie, H.; Sun, J. Z.; Qin, A.; Tang, B. Z. Chem. Commun. 2015, 51, 4830;
(c) Xun, Z. Q.; Tang, H. Y.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Zhang, X. H.; Li, Y. Acta Chim. Sinica 2015, 73, 819(in Chinese). (寻知庆, 唐海云, 曾毅, 陈金平, 于天君, 张小辉, 李嫕, 化学学报, 2015, 73, 819.)
[10] Wang, Z.; Bai, W.; Tong, J.; Wang, Y. J.; Qin, A.; Sun, J. Z.; Tang, B. Z. Chem. Commun. 2016, 52, 10365.
[11] Yang, J.; Li, L.; Yu, Y.; Ren, Z.; Peng, Q.; Ye, S.; Li, Q.; Li, Z. Mater. Chem. Front. 2017, DOI:10.1039/c6qm00014b.
[12] (a) Song, Z.; Zhang, W.; Jiang, M.; Sung, H. H. Y.; Kwok, R. T. K.; Nie, H.; Williams, I. D.; Liu, B.; Tang, B. Z. Adv. Funct. Mater. 2016, 26, 824;
(b) Zhao, Z.; Chen, S.; Chan, C. Y. K.; Lam, J. W. Y.; Jim, C. K. W.; Lu, P.; Chang, Z.; Kwok, H. S.; Qiu, H.; Tang, B. Z. Chem. Asian J. 2012, 7, 484;
(c) Tong, J.; Wang, Y.; Mei, J.; Wang, J.; Qin, A.; Sun, J. Z.; Tang, B. Z. Chem. Eur. J. 2014, 20, 4661;
(d) Wang, Y. J.; Shi, Y.; Wang, Z.; Zhu, Z.; Zhao, X.; Nie, H.; Qian, J.; Qin, A.; Sun, J. Z.; Tang, B. Z. Chem. Eur. J. 2016, 22, 9784.
[13] (a) Shao, A.; Xie, Y.; Zhu S.; Guo, Z.; Zhu, S.; Guo, J.; Shi, P.; James, T. D.; Tian, H.; Zhu, W.-H. Angew. Chem., Int. Ed. 2015, 54, 7275;
(b) Guo, Z.; Shao, A.; Zhu, W.-H. J. Mater. Chem. C 2016, 4, 2640;
(c) Xia, Z. Q.; Shao, A. D.; Li, Q.; Zhu, S. Q.; Zhu, W. H. Acta Chim. Sinica 2016, 74, 351(in Chinese). (夏志清, 邵安东, 李强, 朱世琴, 朱为宏, 化学学报, 2016, 74, 351.)
[14] (a) Ding, L.; Ying, H.-Z.; Zhou, Y.; Lei, T.; Pei, J. Org. Lett. 2010, 12, 5522;
(b) Zhou, Y.; Ding, L.; Shi, K.; Dai, Y.-Z.; Ai, N.; Wang, J.; Pei, J. Adv. Mater. 2012, 24, 957;
(c) Zheng, Y.-Q.; Dai, Y.-Z.; Zhou, Y.; Wang, J.-Y.; Pei, J. Chem. Commun. 2014, 50, 1591;
(d) Saranya, G.; Kolandaivel, P.; Senthilkumar, K. J. Phys. Chem. A 2011, 115, 14647;
(e) Goel, A.; Kumar, V.; Chaurasia, S.; Rawat, M.; Prasad, R.; Anand, R. S. J. Org. Chem. 2010, 75, 3656;
(f) Goel, A.; Sharma, A.; Kathuria, M.; Bhattacharjee, A.; Verma, A.; Mishra, P. R.; Nazir, A.; Mitra, K. Org. Lett. 2014, 16, 756;
(g) Han, L.; Zhang, Y.; Chen, W.; Cheng, X.; Ye, K.; Zhang, J.; Wang, Y. Chem. Commun. 2015, 51, 4477.
[15] Li, X.-G.; Liao, Y.; Huang, M.-R.; Strong, V.; Kaner, R. B. Chem. Sci. 2013, 4, 1970.
[16] (a) Venkatramaiah, N.; Kumar, S.; Patil, S. Chem. Eur. J. 2012, 18, 14745;
(b) Kumar, S.; Venkatramaiah, N.; Patil, S. J. Phys. Chem. C 2013, 117, 7236.
[17] Chandrasekaran, Y.; Venkatramaiah, N.; Patil, S. Chem. Eur. J. 2016, 22, 5288.
[18] (a) Feng, H.-T.; Zheng, Y.-S. Chem. Eur. J. 2014, 20, 195;
(b) Wang, X.; Bian, J.; Xu, L.; Wang, H.; Feng, S. Phys. Chem. Chem. Phys. 2015, 17, 32472.

荧蒽修饰的四苯基乙烯衍生物:分子合成、聚集增强荧光特性及其对苦味酸的高灵敏度检测

Fluoranthene-Modified Tetraphenylethene Derivatives: Synthesis, Aggregation-Enhanced Emission Characteristic and Their Highly Sensitive Detection of Picric Acid

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