Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior

doi:10.6023/A16080406

Acta Chim. Sinica ›› 2016, Vol. 74 ›› Issue (11): 942-948.DOI: 10.6023/A16080406 Previous Articles

Article

具有聚集诱导发光性能的并吡咯衍生物的多晶性和酸响应行为研究

彭喆, 季迎春, 王智, 佟斌, 石建兵, 董宇平

北京理工大学材料学院结构可控先进功能材料与绿色应用重点实验室北京 100081

投稿日期:2016-08-13 发布日期:2016-12-03
通讯作者: 佟斌, 董宇平 E-mail:tongbin@bit.edu.cn;chdongyp@bit.edu.cn
基金资助:
项目受科技部国家基础研究计划973项目（2013CB834704）和国家自然科学基金（Nos.：51328302，21474009）资助.

Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior

Peng Zhe, Ji Yingchun, Wang Zhi, Tong Bin, Shi Jianbing, Dong Yuping

School of Materials Science and Engineering, Beijing Key Laboratory of Construction Tailorable Advanced Functional Materials and Green Applications, Beijing Institute of Technology, Beijing 100081

Received:2016-08-13 Published:2016-12-03
Supported by:
Project supported by the National Basic Research Program of China (973 Program:2013CB834704) and National Natural Science Foundation of China (Nos.:51328302, 21474009).

1. Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior.PDF(930KB)

Abstract

A new A-D-A type pyrrolopyrrole-based derivative 4',4"-(2,5-diphenyl-pyrrolo[3,2-b]pyrrole-1,4-diyl)bis ([1,1'-biphenyl]-4-carbonitrile) (DPPDC) was synthesized via Suzuki coupling reaction between 1,4-bis(4-bromophenyl)-2,5-diphenyl-1,4-dihydropyrrolo[3,2-b]pyrrole and 4-cyanophenylboronic acid. The fluorescent emission intensities of DPPDC in pure THF solution and lower fraction of water (φ_H2O≤60%) mixtures were weak at around 550 nm. When φ_H2O was 99% in THF/H₂O mixtures, the emission was enhanced and blue-shifted at around 505 nm. The maximal fluorescent emission intensity of DPPDC was 11 times higher than that of in pure THF solution, indicating DPPDC exhibiting AIE property. It was also found that four different kinds of crystal structures of DPPDC was cultivated from CHCl₂-Hexane, CHCl₃-Hexane and CHCl₃/Acetone-Hexane systems via solvent slow diffusion method. Four crystals respec-tively emitted blue, azure, green and turquoise at 467, 483, 496 and 493 nm, which manifested the polymorphism-dependent fluorescent emission property of DPPDC. Additionally, trifluoroacetic acid (TFA) could make the emitting color change from yellow to orange-red with as-prepared paper containing DPPDC due to the acid-base interaction. The obvious emitting color change of DPPDC can be used as a visual sensor to detect acid gas.

Key words: polymorphism, pyrrolopyrrole, acid response, aggregation-induced emission

Cite this article

Peng Zhe, Ji Yingchun, Wang Zhi, Tong Bin, Shi Jianbing, Dong Yuping. Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior[J]. Acta Chim. Sinica, 2016, 74(11): 942-948.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Kim, S.; Kim, B.; Lee, J.; Shin, H.; Park, Y.; Park, J. Mat. Sci. Eng. R 2016, 99, 1;
(b)) Zhao, Z.; Li, Z.; Lam, J. W. Y.; Maldonado, J. L.; Ramos-Ortiz, G.; Liu, Y.; Yuan, W.; Xu, J.; Miao, Q.; Tang, B. Z. Chem. Commun. 2011, 47, 6924;
(c) Fujisawa, K.; Okuda, Y.; Izumi, Y.; Nagamatsu, A.; Rokusha, Y.; Sadaike, Y.; Tsutsumi, O. J. Mater. Chem. C 2014, 2, 3549;
(d) Zhao, N.; Zhang, C.; Lam, J. W. Y.; Zhao, Y. S.; Tang, B. Z. Asian J. Org. Chem. 2014, 3, 118;
(e) Mukherjee, S.; Thilagar, P. J. Mater. Chem. C 2016, 4, 2647;
(f) 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. (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.)
[2] Wang, K.; Zhang, H. Y.; Chen, S. Y.; Yang, G. C.; Zhang, J. B.; Tian, W. J.; Su, Z. M.; Wang, Y. Adv. Mater. 2014, 26, 6168.
[3] 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.
[4] Yoon, S. J.; Chung, J. W.; Gierschner, J.; Kim, K. S.; Choi, M. G.; Kim, D.; Park, S. Y. J. Am. Chem. Soc. 2010, 132, 13675.
[5] 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, 1740.
[6] (a) Li, K.; Qin, W.; Ding, D.; Tomczak, N.; Geng, J.; Liu, R.; Liu, J.; Zhang, X.; Liu, H.; Liu, B. Sci. Rep. 2013, 3, 1150;
(b) Wang, D.; Qian, J.; Qin, W.; Qin, A.; Tang, B. Z.; He, S. Sci. Rep. 2014, 4, 4279;
(c) Sun, J. B.; Zhang, G. H.; Jia, X. Y.; Xue, P. C.; Jia, J. H.; Lu, R. Acta Chim. Sinica 2016, 74, 165. (孙静波, 张恭贺, 贾小宇, 薛鹏冲, 贾俊辉, 卢然, 化学学报, 2016, 74, 165.);
(d) Wang, C.; Zhang, H.; Tian, L.; Zhu, W.; Lan, Y.; Li, J.; Wang, H.; Zhang, G. X.; Zhang, D. Q.; Yuan, S. L.; Li, G. T. Sci. China Chem. 2016, 59, 89;
(e) Zhao, Z.; Lam, J. W. Y.; Tang, B. Z. Curr. Org. Chem. 2010, 14, 2109;
(f) Gu, X. G.; Yao, J. J.; Zhang, G. X.; Zhang, C.; Yan, Y. L.; Zhao, Y. S.; Zhang, D. Q. Chem.-Asian J. 2013, 8, 2362;
(g) Li, Z. Z.; Huo, Y. P.; Yang, X. H.; Ji, S. M. Chin. J. Org. Chem. 2016, 36, 2317. (李宗植, 霍延平, 阳香华, 籍少敏, 有机化学, 2016, 36, 2317.)
[7] Mei, J.; Hong, Y. N.; Lam, J. W. Y.; Qin, A. J.; Tang, Y. H.; Tang, B. Z. Adv. Mater. 2014, 26, 5429.
[8] He, Z. K.; Zhang, L. Q.; Mei, J.; Zhang, T.; Lam, J. W.Y.; Shuai, Z. G.; Dong, Y. Q.; Tang, B. Z. Chem. Mater. 2015, 27, 6601.
[9] Xu, Y. X.; Wang, K.; Zhang, Y. J.; Xie, Z. Q.; Zou, B.; Ma, Y. G. J. Mater. Chem. C 2016, 4, 1257.
[10] Zhang, Z. Y.; Song, X. X.; Wang, S. P.; Li, F.; Zhang, H. Y.; Ye, K. Q.; Wang, Y. J. Phys. Chem. Lett. 2016, 7, 1697.
[11] Krzeszewski, M.; Thorsted, B.; Brewer, J.; Gryko, D. T. J. Org. Chem. 2014, 79, 3119.
[12] Hisaki, I.; Sakamoto, Y.; Shigemitsu, H.; Tohnai, N.; Miyata, M. Cryst. Growth Des. 2009, 9, 414.
[13] Janiga, A.; Glodkowska-Mrowka, E.; Stoklosa, T.; Gryko, D. T. Asian J. Org. Chem. 2013, 2, 411.
[14] Peng, Z.; Feng, X.; Tong, B.; Chen, D. D.; Shi, J. B.; Zhi, J. G.; Dong, Y. P. Sensor Actuat. B 2016, 232, 264.
[15] Zhu, X. L.; Huang, H.; Liu, R.; Jin, X. D.; Li, Y. H.; Wang, D. F.; Wang, Q.; Zhu, H. J. J. Mater. Chem. C 2015, 3, 3774.

具有聚集诱导发光性能的并吡咯衍生物的多晶性和酸响应行为研究

Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Zeng Chongyang, Hu Ping, Wang Biqin, Fang Wenyan, Zhao Keqing, Donnio Bertrand. Star-shaped Triphenylene-triazine Multi-stimuli Responsive Discotic Liquid Crystals: Synthesis, Properties and Applications [J]. Acta Chimica Sinica, 2023, 81(5): 469-479.
[2]	Yanqin Huang, Lijun Li, Shupei Yang, Rui Zhang, Xingfen Liu, Quli Fan, Wei Huang. HA-AuNPs/FDF for Highly Sensitive Detection of Hyaluronidase, Tumor-targeting Fluorescence Cell Imaging and Phototherapy [J]. Acta Chimica Sinica, 2023, 81(12): 1687-1694.
[3]	Bin Liu, Pangkuan Chen. Synthesis and Properties of Novel Circularly Polarized Luminescence Materials Based on Binaphthol Skeleton [J]. Acta Chimica Sinica, 2022, 80(7): 929-935.
[4]	Lulu Zhang, Yuanyuan Wang, Guinan Zhu, Wenbo Dai, Zixuan Zhao, Ying Zhao, Junge Zhi, Yuping Dong. Aggregation-Induced Emission and Mechanochromism of the Tetraphenylbutadiene Derivatives Containing Different Alkyl Chains [J]. Acta Chimica Sinica, 2022, 80(3): 282-290.
[5]	Heqi Gao, Di Jiao, Hanlin Ou, Jingtian Zhang, Dan Ding. High Performance Aggregation-Induced Emission Nanoprobes for Image-Guided Cancer Surgery [J]. Acta Chimica Sinica, 2021, 79(3): 319-325.
[6]	Yueying Lai, Zihao Zhao, Shuyuan Zheng, Wang Zhang Yuan. Polymorphism-Dependent Emission of Nonaromatic Luminophores [J]. Acta Chimica Sinica, 2021, 79(1): 93-99.
[7]	Guan Xiaolin, Li Zhifei, Wang Lin, Liu Meina, Wang Kailong, Yang Xueqin, Li Yali, Hu Lili, Zhao Xiaolong, Lai Shoujun, Lei Ziqiang. Preparation of AIE Polymer Dots (Pdots) Based on Poly(N-vinyl-2-pyrrolidone)-Eu(III) Complex and Dual-color Live Cell Imaging [J]. Acta Chimica Sinica, 2019, 77(12): 1268-1278.
[8]	Xia Zhiqing, Shao Andong, Li Qiang, Zhu Shiqin, Zhu Weihong. Substituent Effect on Quinoline-Malononitrile AIE Fluorescent Properties [J]. Acta Chim. Sinica, 2016, 74(4): 351-355.
[9]	Sun Jingbo, Zhang Gonghe, Jia Xiaoyu, Xue Pengchong, Jia Junhui, Lu Ran. Synthesis, Mechanochromism and Acid Response of the Fluorescence Dyes Based on Quinoxalines Modified with Tetraphenylethylenes [J]. Acta Chim. Sinica, 2016, 74(2): 165-171.
[10]	Han Ting, Cathy K. W. Jim, Jacky W. Y. Lam, Tang Ben Zhong. Polyynes with Aggregation-Induced Emission Characteristics: Synthesis and Their Photonic Properties [J]. Acta Chim. Sinica, 2016, 74(11): 877-884.
[11]	Bin Xin, Luo Weijian, Yuan Wangzhang, Zhang Yongming. Clustering-Triggered Emission of Poly(N-hydroxysuccinimide Methacrylate) [J]. Acta Chim. Sinica, 2016, 74(11): 935-941.
[12]	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.
[13]	Guan Weijiang, Zhou Wenjuan, Lü Chao. Ultrathin Luminescence Film Based on Gold Nanoclusters with Aggregation-Induced Emission [J]. Acta Chim. Sinica, 2016, 74(11): 929-934.
[14]	Ji Guang, Yan Lulin, Wang Hui, Ma Lian, Xu Bin, Tian Wenjing. Efficient Near-infrared AIE Nanoparticles for Cell Imaging [J]. Acta Chim. Sinica, 2016, 74(11): 917-922.
[15]	Huang Yuzhang, Lei Luoqi, Zheng Chao, Wei Bo, Zhao Zujin, Qin Anjun, Hu Rongrong, Tang Ben Zhong. Tetraphenylethene-Containing Alkynone Derivatives: Design and Synthesis, Aggregation-Induced Emission Characteristics, and the Selective Fluorescence Detection of Pd²⁺ [J]. Acta Chim. Sinica, 2016, 74(11): 885-892.