Hydrophilic Fluorescent Probes for Fe3+ Ions Based on Nanoparticles of Twisting D-π-A Type Compound Derived from Benzylidenemalononitrile

doi:10.6023/cjoc201911002

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1588-1597.DOI: 10.6023/cjoc201911002 Previous Articles Next Articles

基于苯亚甲基丙二腈D-π-A型化合物纳米粒子的Fe^3＋亲水荧光探针

刘幸^a, 陶鹏^b,d, 杨晶晶^a, 刘雯^a, 王华^a, 王学宁^c, 赵强^d, 黄维扬^b, 许并社^a

a 太原理工大学新材料界面科学与工程教育部重点实验室山西太原 030024;
b 香港理工大学应用生物与化学技术系香港 999077;
c 山西白求恩医院(山西医学科学院) 心脏大血管外科山西太原 030032;
d 南京邮电大学有机电子与信息显示国家重点实验室培育基地南京 210023

收稿日期:2019-11-04 修回日期:2020-01-27 发布日期:2020-04-09
通讯作者: 王华, 许并社 E-mail:wanghua001@tyut.edu.cn;xubs@tyut.edu.cn
基金资助:
国家自然科学基金（Nos.61775155，61605138，61705156，61905120）、山西省科技创新重点团队（No.201601D021043）、香港理工大学（Nos.1-ZE1C，847S）资助项目.

Hydrophilic Fluorescent Probes for Fe³⁺ Ions Based on Nanoparticles of Twisting D-π-A Type Compound Derived from Benzylidenemalononitrile

Liu Xing^a, Tao Peng^b,d, Yang Jingjing^a, Liu Wen^a, Wang Hua^a, Wang Xuening^c, Zhao Qiang^d, Wong Wai-yeung^b, Xu Bingshe^a

a Key Laboratory of Interface Science and Engineering in Advanced Materials of Ministry of Education, Taiyuan University of Technology, Taiyuan, Shanxi 030024;
b Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong 999077;
c Department of Cardiovascular Surgery, Shanxi Baiqiuen Hospital(Shanxi Academy of Medical Sciences), Taiyuan, Shanxi 030032;
d Key Laboratory for Organic Electronics and Information Displays and Institute of Advanced Materials, Nanjing University of Posts and Telecommunications(NUPT), Nanjing 210023

Received:2019-11-04 Revised:2020-01-27 Published:2020-04-09
Supported by:
Project supported by the National Natural Scientific Foundation of China (Nos. 61775155, 61605138, 61705156, 61905120), the Shanxi Provincial Key Innovative Research Team in Science and Technology (No. 201601D021043), and the Hong Kong Polytechnic University (No. 1-ZE1C and 847S).

1. 201588S.pdf(865KB)

Abstract

In this work, the novel fluorescent probes for detecting Fe³⁺ ions based on nanoparticles (TA-DF-BDM/PSMA NPs) of fluorescence material with twisting D-π-A configuration was designed and prepared, in which triphenylamine (TA), 9,9-dioctylfluorene (DF) and benzylidenemalononitrile (BDM) serve as electron donor (D) unit, π conjugated unit, and electron acceptor (A) unit, respectively. TA-DF-BDM/PSMA NPs exhibit red-emission peak located at 610 nm in photoluminescence spectrum and larger stokes shifts (ca. 203 nm). And, TA-DF-BDM/PSMA NPs exhibit high selectivity for detecting Fe³⁺ ions in pure water with high sensitivity and low detection limit of 0.9833 μmol/L. More importantly, TA-DF-BDM/PSMA NPs show such properties as good photophysical stability, reversibility, excellent biocompatibility and low cytotoxicity, which can be utilized in bioimaging investigations.

Key words: fluorescent probes, Fe³⁺ ions, hydrophilcity, reversibility

Cite this article

Liu Xing, Tao Peng, Yang Jingjing, Liu Wen, Wang Hua, Wang Xuening, Zhao Qiang, Wong Wai-yeung, Xu Bingshe. Hydrophilic Fluorescent Probes for Fe³⁺ Ions Based on Nanoparticles of Twisting D-π-A Type Compound Derived from Benzylidenemalononitrile[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1588-1597.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Atchudan, R.; Edison, T. N. J. I.; Aseer, K. R.; Perumal, S.; Karthik, N.; Lee, Y. R. Biosens. Bioelectron. 2018, 99, 303.
[2] Li, Y.; Chang, Z. L.; Huang, F.; Wu, P. Y.; Chu, H. C.; Wang, J. Dalton Trans. 2018, 47, 9267.
[3] Choi, Y. W.; Park, G. J.; Na, Y. J.; Jo, H. Y.; Lee, S. A.; You, G. R.; Kim, C. Sens. Actuators, B 2014, 194, 343.
[4] Chen, L.; Wu, C. L.; Du, P.; Feng, X. W.; Wu, P.; Cai, C. X. Talanta 2017, 164, 100.
[5] Kaur, K.; Chaudhary, S.; Singh, S.; Mehta, S. K. Sens. Actuators, B 2016, 232, 396.
[6] Ghosh, D.; Luwang, M. N. J. Lumin. 2016, 171, 1.
[7] Sharma, D.; Kuba, A.; Thomas, R.; Kumar, R.; Choi, H. J.; Sahoo, S. K. Spectrochim. Acta, Part A 2016, 153, 393.
[8] Liu, F. J.; Yao, J.; Fan, C.; Zhang, L. Y.; Hua, Y; Zhang. C. X; Song, N.; Kong, Y. J. New J. Chem. 2018, 42, 9676.
[9] Lee, M. H.; Kim, J. S.; Sessler, J. L. Chem. Soc. Rev. 2015, 44, 4185.
[10] Ma, J.; Yu, H. H.; Jiang, X.; Luo, Z. Z.; Zheng, Y. Sens. Actuators, B 2019, 281, 989.
[11] Liu, Y. H.; Duan, W. X.; Song, W.; Liu, J. J.; Ren, C. L.; Wu, J.; Liu, D.; Chen, H. L. ACS Appl. Mater. Interfaces 2017, 9, 12663.
[12] Rao, L. S.; Tang, Y.; Li, Z. T.; Ding, X. R.; Liang, G. W.; Lu, H. G.; Yan, C. M.; Tang, K. R.; Yu, B. H. Mater. Sci. Eng., C 2017, 81, 213.
[13] Wu, S.; Chen, Y.; Sung, Y. Analyst 2018, 99, 303.
[14] Feng, H.; Meng, Q. T.; Wang, Y.; Duan, C. C.; Wang, C. P.; Jia, H. M.; Zhang, Z. Q.; Zhang, R. Chem.-Asian. J. 2018, 13, 2573.
[15] Asanuma, D.; Sakabe, M.; Kamiya, M.; Yamamoto, K.; Hiratake, J.; Ogawa, M.; Kosaka, N.; Choyke, P. L.; Nagano, T.; Kobayashi, H. Nat. Commun. 2015, 6, 6463.
[16] Chhatwal, M.; Kumar, A.; Singh, V.; Gupta, R. D.; Awasthi, S. K. Coord. Chem. Rev. 2015, 292, 30.
[17] Tao, P.; Miao, Y. Q.; Wang, H.; Xu, B. S.; Zhao, Q. Chem. Rec. 2019, 19, 1531.
[18] Xing, J.; Liu, D.; Zhou, G. X.; Li, Y.; Wang, P.; Hu, K.; Gu, N.; Ji, M. Colloids Surf., B 2017, 160, 265.
[19] Liu, Y. M.; Shen, R.; R, J. X.; Yao, X.; Yang, Y.; Liu, H. L.; Tang, X. L.; Bai, D. C.; Zhang, G. L; Liu, W. S. RSC Adv. 2016, 6, 111754.
[20] Manikandan, I.; Chang, C. H.; Chen, C. L.; Sathish, V.; Li, W. S.; Malathi, M. Spectrochim. Acta, Part A 2017, 182, 58.
[21] Jung, H. J.; Singh, N.; Jang, D. O.; Tetrahedron Lett. 2008, 49, 2960.
[22] Wang, P.; Zhou, D. G.; Chen, B. Spectrochim. Acta, Part A 2019, 207, 276.
[23] Feng, X.; Li, Y.; He, X. W.; Liu, H. X.; Zhao, Z.; Ryan, T. K. K.; Mark, R. J. E.; Jaeky, W. Y.; Lam, J. W. Y.; Tang, B. Z. Adv. Funct. Mater. 2018, 28, 1802833.
[24] Yang, C. C; Zhang, J.; Peng, W. T.; Sheng, W.; Liu, D. Y.; Kuttipillai, P. S.; Young, M.; Donahue, M. R.; Levine, B. G; Borhan, B.; Lunt, R. R. Sci. Rep. 2018, 8, 16359.
[25] Wang, N.; Arulkumar, M.; Chen, X. Y.; Wang, B. W.; Chen, S. H.; Yao, C.; Wang, Z. Y. J. Org. Chem. 2019, 39, 2771(in Chinese). (王能, Arulkumar, M., 陈孝云, 王柏文, 陈思鸿, 姚辰, 汪朝阳, 有机化学, 2019, 39, 2771.)
[26] Feng, Z. Y; Tao, P.; Zou, L.; Gao, P. L.; Liu, Y.; Liu, X.; Wang, H.; Liu, S. J.; Dong, Q. C.; Li, J.; Xu, B. S; Huang, W.; Wong, W. Y.; Zhao, Q. ACS Appl. Mater. Interfaces 2017, 9, 28319.
[27] Zhang, Z. Y.; Lu, S. Z.; Sha, C. M.; Xu, D. M. Sens. Actuators, B 2015, 208, 258.
[28] Wan, Q. Q.; Chen, S. M.; Shi, W.; Li, L. H.; Ma, H. M. Angew. Chem., Int. Ed. 2014, 53, 10916.
[29] Jiang, M. J.; Gu, X. G.; Lam, J. W. Y.; Zhang, Y. L.; Kwok, R. T. K.; Wong, K. S.; Tang, B. Z. Chem. Sci. 2017, 8, 5440.
[30] Yang, X. D; Chen, X. L; Lu, X. D.; Yan, C. G.; Xu, Y. K.; Hang, X. D.; Qu, J. Q.; Liu, R. Y. J. Mater. Chem. 2016, 4, 383.
[31] Wang, L. Y.; Fang, G. P.; Cao, D. R. Sens. Actuators, B 2015, 207, 849.
[32] Wu, X. M.; Guo, Z. Q.; Wu, Y. Z.; Zhu, S. Q.; Tony, D. J.; Zhu, W. H. ACS Appl. Mater. Interfaces 2013, 5, 12215.
[33] Shi, B. F.; Su, Y. B.; Zhang, L. L.; Huang, M. J.; Liu, R. J.; Zhao, S. L. ACS Appl. Mater. Interfaces 2016, 8, 10717.

基于苯亚甲基丙二腈D-π-A型化合物纳米粒子的Fe^3＋亲水荧光探针

Hydrophilic Fluorescent Probes for Fe³⁺ Ions Based on Nanoparticles of Twisting D-π-A Type Compound Derived from Benzylidenemalononitrile

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 8

Recommended Articles

Metrics

Comments

[1]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[2]	Zhaohua Chen, Xiying Cao, Sihong Chen, Shiwei Yu, Yanlan Lin, Shuting Lin, Zhaoyang Wang. Design, Synthesis and Application of Trisubstituted Olefinic Aggregation-Induced Emission Molecules [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2355-2363.
[3]	Na Li, Xiaofeng Tan, Qinglai Yang. Recent Progress on Strategies and Applications of Imaging for Intestinal Microflora [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1375-1386.
[4]	Lü Taoyuze, Zhu Kangning, Liu Bin. Recent Advances of Organic Fluorescent Probes for Detection of Human Serum Albumin [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2786-2795.
[5]	Li Meihan, Wang Yutong, Liu Guangjian, Lü Haijuan, Xing Guowen. Recent Progress on Lysosome-Targetable Fluorescent Probes [J]. Chin. J. Org. Chem., 2017, 37(2): 356-374.
[6]	Li Yangjie, Lü Ziqi, Liu Min, Xing Guowen. Recent Progresses on Mitochondria-Targetable Fluorescent Probes [J]. Chin. J. Org. Chem., 2016, 36(5): 962-975.
[7]	Sun Jingfu, Qian Ying. Synthesis and Fluorescent Properties of Water-Soluble 1,8-Naphthalimide Dendron [J]. Chin. J. Org. Chem., 2015, 35(5): 1104-1111.
[8]	Chen Jiaxuan, Tian Yi, Xiang Qingxiang, Xiong Junru, Zhang Liqun, Li Yan. A Reversible Fluorescence Enhancement Probe for Hg²⁺ Based on Rhodamine and Its Application in Live Cell Imaging [J]. Chin. J. Org. Chem., 2013, 33(10): 2210-2215.

基于苯亚甲基丙二腈D-π-A型化合物纳米粒子的Fe3＋亲水荧光探针