Synthesis and Properties Characterization of Novel Fe3+ Fluorescent Probe Based on Rhodamine B

doi:10.6023/cjoc201407018

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 175-180.DOI: 10.6023/cjoc201407018 Previous Articles Next Articles

Articles

基于罗丹明B新型Fe³⁺荧光探针的合成及其性能研究

苏娜, 杨美盼, 孟文斐, 杨秉勤

合成与天然功能分子化学教育部重点实验室西北大学化学与材料科学学院西安 710069

收稿日期:2014-07-10 修回日期:2014-08-22 发布日期:2014-09-12
通讯作者: 杨秉勤 E-mail:yangbq@nwu.edu.cn
基金资助:
国家自然科学基金(No. 21172178)资助项目.

Synthesis and Properties Characterization of Novel Fe³⁺ Fluorescent Probe Based on Rhodamine B

Su Na, Yang Meipan, Meng Wenfei, Yang Bingqin

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069

Received:2014-07-10 Revised:2014-08-22 Published:2014-09-12
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172178)

1. Synthesis and Properties Characterization of Novel Fe³⁺ Fluorescent Probe Based on Rhodamine B.PDF(475KB)

Abstract

A novel rhodamine B derivative R1 was synthesized facilely by the condensation reaction of rhodamine B and 2,6-diaminopyridine, and its structure was characterized by ¹H NMR, ¹³C NMR, IR, HRMS-ESI, X-ray techniques and elemental analysis. The results showed that the compound R1 exhibited the selective colorimetric to Fe³⁺, and other metal ions did not interfere with its recognition. The fluorescence intensity of probe R1 and Fe³⁺ concentration (4×10^-6～1.6×10^-5 mol/L) showed a good linear relationship. What's more, probe R1 has been applied to image intracellular Fe³⁺ in living HepG2 cells.

Key words: rhodamine B, fluorescent probe, iron ion, recognition, fluorescence intensity, HepG2 living cells

Cite this article

Su Na, Yang Meipan, Meng Wenfei, Yang Bingqin. Synthesis and Properties Characterization of Novel Fe³⁺ Fluorescent Probe Based on Rhodamine B[J]. Chin. J. Org. Chem., 2015, 35(1): 175-180.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Lin, W.-Y.; Long, L.-L.; Yuan, L.; Cao, Z.-M.; Feng, J.-B. Anal. Chim. Acta 2009, 634, 262.
[2] (a) Eisenstein, R. S. Annu. Rev. Nutr. 2000, 20, 627. (b) Rouault, T. A. Nat. Chem. Biol. 2006, 2, 406.
[3] Yin, W.-T.; Cui, H.; Yang, Z.; Li, C.; She, M.-Y.; Yin, B. Sens. Actuators, B 2011, 157, 675.
[4] Wang, S.-X.; Meng, X.-M.; Zhu, M.-Z. Tetrahedron Lett. 2011, 52, 2840.
[5] Cabon, J. Y.; Giamarchi, P.; Bihan, A. L. Anal. Chim. Acta 2010, 664, 114.
[6] Saracoglu, S.; Soylak, M.; Peker, D. S.; Elci, L.; Santos dos, W. N.; Lemos, V. A.; Fer-reira, S. L. Anal. Chim. Acta 2006, 575, 133.
[7] Lunvongsa, S.; Oshima, M.; Motomizu, S. Talanta 2006, 68, 969.
[8] Pomazal, K.; Prohaska, C.; Steffan, I.; Reich, G.; Huber, J. F. K. Analyst 1999, 124, 657.
[9] Bakkaus, E.; Collins, R. N.; Morel, J. L. J. Chromatogr. A 2006, 1129, 208.
[10] Ugo, P.; Moretto, L. M.; Boni, A. D. Anal. Chim. Acta 2002, 427, 147.
[11] Xiang, Y.; Tong, A. J. Org. Lett. 2006, 8, 1549.
[12] Hu, Z.-Q.; Feng, Y.-C.; Huang, H.-Q,; Ding, L.; Wang, X.-M.; Lin, C.-S.; Li, M.; Ma, C.-P. Sens. Actuators, B 2011, 156, 428.
[13] Meng, W.-F.; Yang, M.-P.; Cheng, Z.; Li, S.-N.; Yang, B.-Q. Chin. J. Org. Chem. 2013, 33, 398 (in Chinese). (孟文斐, 杨美盼, 成昭, 李少妮, 杨秉勤, 有机化学, 2014, 33, 398.)
[14] Meng, Q.-T.; Su, W.-P. Talanta 2012, 97, 456.
[15] Yang, M.-P.; Xu, C.-C.; Li, S.-N.; Cheng, Z.; Zhou, J.; Yang, B.-Q. RSC Adv. 2014, 4, 14248.
[16] Lin, W.; Long, L.; Yuan, L.; Cao, Z.; Feng, J. Anal. Chim. Acta 2009, 634, 262.
[17] Sun, W.; Hu, D.-Y.; Wu, Z.-B.; Song, B.-A.; Yang, S. Chin. J. Org. Chem. 2011, 31, 997 (in Chinese). (孙伟, 胡德禹, 吴志兵, 宋宝安, 杨松, 有机化学, 2011, 31, 997.)
[18] Su, W.-Q.; Tong, J.; Yang, B.-Q. Chin. J. Org. Chem. 2013, 33, 982 (in Chinese). (苏文崎, 童杰, 杨秉勤, 有机化学, 2013, 33, 982.)
[19] Li, N.; Liu, M.-L.; Yin, W.-T.; Yang, Z.; Li, J.-L.; Shi, Z. Chin. J. Org. Chem. 2011, 31, 39 (in Chinese). (李娜, 刘美玲, 尹文婷, 杨征, 李剑利, 史真, 有机化学, 2011, 31, 39.)
[20] Zhou, Y.; Wang, F.; Kim, Y.; Kim, S. J.; Yoon, J. Org. Lett. 2009, 11, 4442.
[21] Huang, W.-J.; Wu, W.-H.; Liang, J.-X. Acta Chim. Sinica 2012, 70, 873 (in Chinese). (黄文君, 吴文辉, 梁嘉香, 化学学报, 2012, 70, 873.)
[22] Du, J.-J.; Fan, J.-L.; Peng, X.-J.; Sun, P. P.; Wang, J.-Y. Org. Lett. 2010, 12, 476.
[23] Ge, F.; Ye, H.; Zhang, H.; Zhao, B.-X. Dyes Pigm. 2013, 99, 661.
[24] Ji, S.-Z.; Meng, X.-M.; Ye, W.-P.; Feng, Y.; Sheng, H.-T.; Cai, Y.-L.; Liu, J.-S.; Zhu, X.-F.; Guo, Q.-X. Dalton Trans. 2014, 43, 1583.
[25] Liu, S.-R.; Wu, S.-P. Sens. Actuators, B 2012, 171-172, 1110.
[26] Hu, Z.-Q.; Du, M.; Zhang, L.-F.; Guo, F.-Y.; Liu, M.-D.; Li, M. Sens. Actuators, B 2014, 192, 439.
[27] Huang, J.-H.; Xu, Y.-F.; Qian, X.-H. Dalton Trans. 2014, 43, 5983.
[28] Li, C.-Y.; Zou, C.-X.; Li, Y.-F.; Tang, J.-L.; Weng, C. Dyes Pigm. 2014, 104, 110.
[29] Piao, J. Y.; Lv, J.; Zhou, T.; Wu, X. Spectrochim. Acta, Part A 2014, 128, 475.
[30] Sheng, H.-J.; Meng, X.-M.; Ye, W.-P.; Feng, Y.; Sheng, X.-W.; Guo, Q.-X. Sens. Actuators, B 2014, 195, 534.
[31] Wang, J.-H.; Zhang, D.; Liu, Y.-Q.; Ding, P.-G.; Wang, C.-C.; Ye, Y.; Zhao, Y.-F. Sens. Actuators, B 2014, 191, 344.
[32] Chai, M.-M. M.S. Thesis, Zhengzhou University, Zhengzhou, 2012 (in Chinese). (柴梅梅, 硕士论文, 郑州大学, 郑州, 2012.)
[33] Yang, Z.; She, M.-Y.; Yin, B.; Cui, J.-H.; Zhang. Y.-Z.; Sun, W.; Li, J.-L.; Shi, Z. J. Org. Chem. 2012, 77, 1143.

基于罗丹明B新型Fe³⁺荧光探针的合成及其性能研究

Synthesis and Properties Characterization of Novel Fe³⁺ Fluorescent Probe Based on Rhodamine B

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yingzhen Zhang, Dandan Jiang, Juanhua Li, Jingjing Wang, Kunming Liu, Jinbiao Liu. Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 41-53.
[2]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[3]	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.
[4]	Binghui Ding, Shaohui Han, Haiqing Xiong, Benhua Wang, Bojun Zuo, Xiangzhi Song. A Highly Selective Ratiometric Fluorescent Probe for the Detection of Hypochlorite in Acute Lung Injury [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2878-2884.
[5]	Yifang Li, Yao Wang, Huawei Niu, Xiujin Chen, Zhaozhou Li, Yongguo Wang. Research Progress of Sulfur Dioxide Fluorescent Probe Targeting Mitochondria [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1952-1962.
[6]	Feiran Liu, Jing Jing, Xiaoling Zhang. Research Progress of Fluorescent Probes for Cysteine Targeting Cellular Organelles [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2053-2067.
[7]	Tiantian Liu, Hongpeng Zhang, Xiaomeng Jiao, Yinjuan Bai. Research Progress of Multi-signal Fluorescent Probes for Simultaneous Detection of Biothiols [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2081-2095.
[8]	Zhihua Chen, Yan Hu, Lili Ma, Ziyi Zhang, Chuanxiang Liu. Rational Design of ortho-Vinylhydropyridine-Assisted Amino-fluorophore as Hypochlorite Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 718-724.
[9]	Hongwei Tang, Chao Wang, Keli Zhong, Shuhua Hou, Lijun Tang, Yanjiang Bian. A Naked-Eye and Fluorescent Dual-Channel Probe for Rapid Detection of Hg²⁺ and Its Multiple Applications [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 712-717.
[10]	Huiming Lu, Lamaocao Ma, Hengchang Ma. Research Progress and Prospect of Aggregation-Induced Emission Supramolecular Luminescence Materials [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4075-4105.
[11]	Meng Liu, Yanru Huang, Xiaofei Sun, Lijun Tang. An “Aggregation-Induced Emission+Excited-State Intramolecular Proton Transfer” Mechanisms-Based Benzothiazole Derived Fluorescent Probe and Its ClO^–Recognition [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 345-351.
[12]	Yangyang Li, Xiaofei Sun, Xiaoling Hu, Yuanyuan Ren, Keli Zhong, Xiaomei Yan, Lijun Tang. Synthesis of Triphenylamine Derivative and Its Recognition for Hg²⁺ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 320-325.
[13]	Jidong Zhang, Wanlin Yan, Wenqiang Hu, Dian Guo, Dalong Zhang, Xiaoxin Quan, Xianpan Bu, Siyu Chen. Design and Synthesis of a Zn²⁺ Fluorescent Probe Based on Aggregation Induced Luminescence Properties [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 326-331.
[14]	Yanhui Ma, Yuqian Wu, Xiaoxu Wang, Gui Gao, Xin Zhou. Research Progress of Near-Infrared Fluorescent Probes Based on 1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO) [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 94-111.
[15]	Yaxin Yang, Lin Chen, Xiaoling Hu, Keli Zhong, Shidi Li, Xiaomei Yan, Jinglin Zhang, Lijun Tang. Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 308-312.

基于罗丹明B新型Fe3+荧光探针的合成及其性能研究