一种具有聚集诱导发光性质的Fe3+荧光探针的合成及性能研究
收稿日期: 2017-06-28
修回日期: 2017-08-08
网络出版日期: 2017-09-15
基金资助
新疆维吾尔自治区自然科学基金（No.2015211B024）和新疆师范大学博士启动基金（No.XJNUBS1508）资助项目.
Study on a Novel Colorimetric and Off-On Fluorescent Chemosensor with Aggregation-Induced Emission Effect for Detection of Fe3+ in Aqueous Solution
Received date: 2017-06-28
Revised date: 2017-08-08
Online published: 2017-09-15
Supported by
Project supported by the Natural Science Foundation of Xinjiang Uygur Aotonomous Region (No. 2015211B024) and the Doctoral Scientific Research Foundation of Xinjiang Normal University (No. XJNUBS1508).
通过乙二醛将1，1-二（4-甲基苯基）-2-（4-氨基苯基）-2-苯基乙烯和罗丹明B酰肼连接起来，合成了一种四苯乙烯官能团化的罗丹明B衍生物TPE-RhB.利用IR，NMR，MS和元素分析等对其进行了表征，确定了分子结构.并通过循环伏安分析法、紫外-可见光谱法、分子荧光光谱法等分别考察了它的电化学和光学性质.研究表明TPE-RhB的电子亲合能为3.66 eV，有望开发为电子传输材料.此化合物在纯乙醇溶液中，几乎没有荧光，在乙醇/水的混合溶剂中具有典型聚集诱导发光（AIE）性能.更为重要的是在乙醇/水（V：V=1：1，Tris-HCl pH 7.0）混合溶液中能对Fe3+实现"off-on"荧光识别，并裸眼可观察到溶液颜色从淡黄色变成粉红色，且几乎不受其他共存离子的干扰.探针与Fe3+的结合常数为3.12×103，检出限可达3.53×10-7 mol·L-1，Fe3+离子含量范围在6×10-5~1.8×10-4 mol·L-1时，荧光强度与Fe3+离子浓度呈良好的线性关系（R2=0.9915），并通过Job's曲线、紫外和荧光滴定、核磁滴定初步确定了化合物TPE-RhB和Fe3+的络合机理.
刘瑞姣 , 曾竟 . 一种具有聚集诱导发光性质的Fe3+荧光探针的合成及性能研究[J]. 有机化学, 2017 , 37(12) : 3274 -3281 . DOI: 10.6023/cjoc201706037
A novel tetraphenylethyene-functionalized rhodamine derivative (TPE-RhB) was designed and synthesized. FT-IR, NMR, MS, elemental analysis, cyclic voltammetry electrochemical analysis, UV-Vis, and molecular fluorescence were used to study its structure, electrochemical and optical properties. These results showed that the electron affinity of TPE-RhB was 3.66 eV, which is expected to develop electron-transporting material. A significant aggregation-induced emission (AIE) effect of TPE-RhB was found through solution fluorescence test in different V(EtOH):V(H2O) mixed solvents. Furthermore, sensor TPE-RhB displayed highly seletive and sensitive off-on fluorescence response and naked-eye color change to Fe3+ in EtOH/H2O (V:V=1:1, Tris-HCl pH 7.0) solution. The association constant between TPE-RhB and Fe3+ was detected to be 3.12×103 and the detection limit was calculated to be 3.53×10-7 mol·L-1. The probe TPE-RhB also showed a good linearity (R2=0.9915) in the range of 60~180 μmol/L of Fe3+ ion. The mechanisms had been supported by Job's plot evalution, fluorescence titrations, and 1H NMR spectroscopic studies.
[1] Luo, J.-D.; Xie, Z.-L.; Lam, J. W. Y.; Lin, C. Chem. Commun. 2001, 18, 1740.
[2] You, X.; Zhang, G.-X.; Zhan, C.; Wang, Y.-C.; Zhang, D.-Q. ACS Symp. Ser. 2016, 93, 1227.
[3] Wang, Q.; Li, Z.; Tao, D.-D.; Zhang, Q.; Zhang, P.; Guo, D.-P.; Jiang, Y.-B. Chem. Commun. 2016, 52, 12929.
[4] Zhang, G.-X.; Hu, F.; Zhang, D.-Q. Langmuir 2015, 31, 4593.
[5] Wang, L.-Y.; Yang, L.-L.; Cao, D.-R. Curr. Org. Chem. 2014, 18, 1028.
[6] Yang, Y.; Huang, Y.-Y.; Zhang, G.-X.; Zhao, R.; Zhang, D.-Q. Acta Chim. Sinica 2016, 74, 871(in chinese). (杨阳, 黄嫣嫣, 张关心, 赵睿, 张德清, 化学学报, 2016, 74, 871.)
[7] Li, Z.-Z.; Huo, Y.-P.; Yang, X.-H.; Ji, S.-M. Chin. J. Org. Chem. 2016, 36, 2317(in Chinese). (李宗植, 霍延平, 阳香华, 籍少敏, 有机化学, 2016, 36, 2317.)
[8] Gabr, M. T.; Pigge, F. C. Dalton Trans. 2016, 45, 14039.
[9] Jiang, G.-Y.; Liu, X.; Wu, Y.-Q.; Wang, J.-G.; Dong, X.-B.; Zhang, G.-X.; Li, Y.-D.; Fan, X.-L. RSC Adv. 2016, 6, 59400.
[10] Xiong, J.-B.; Xie, W.-Z.; Sun, J.-P.; Wang, J.-H.; Zhu, Z.-H.; Feng, H.-T.; Guo, D.; Zhang, H.; Zheng, Y.-S. J. Org. Chem. 2016, 81, 3720.
[11] Zhao, N.; Chen, S.-J.; Hong, Y.-N.; Tang, B.-Z. Chem. Commun. 2015, 51, 13599.
[12] Huang, J.; Li, Q.-Q.; Li, Z.-J. J. Mol. Eng. Mater. 2013, 1, 1.
[13] Wu, F.; Shan, Y.-H.; Li, X.-L.; Song, Q.-L.; Zhu, L.-N. Org. Electron. 2016, 39, 323.
[14] Wu, F.; Liu, J.-L.; Wang, G.; Song, Q.-L.; Zhu, L.-N. Chem. Eur. J. 2016, 22, 16636.
[15] Zhao, D.-Y. ACS Symp. Ser. 2016, 2, 151.
[16] Takeda, T.; Yamamoto, S.; Mitsuishi, M.; Akutagawa, T. Org. Biomol. Chem. 2016, 14, 8922.
[17] Ramya, A. N.; Joseph, M. M.; Nair, J. B.; Karunakaran, V.; Narayanan, N.; Maiti, K. K. ACS Appl. Mater. Inter. 2016, 8, 10220.
[18] Huang, J.; Yang, M.; Yang, J.; Tang, R.; Ye, S.; Li, Q.; Li, Z. Org. Chem. Front. 2015, 12, 1608.
[19] Lu, D.-Q.; He, L.; Wang, Y.-Y.; Xiong, M.-Y.; Hu, M.-M.; Liang, H.; Huan, S.-Y.; Zhang, X.-B.; Tan, W.-H. Talanta 2017, 167, 550.
[20] Akul, S. G.; Kamaldeep, P.; Vijay, L. Sens. Actuators,B 2017, 246, 653.
[21] Yan, Y.-Y.; Che, Z.-P.; Yu, X.; Zhi, X.-Y.; Wang, J.-J.; Xu, H. Bioorg. Med. Chem. 2013, 21, 508.
[22] Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2012, 112, 1910.
[23] 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.)
[24] Liu, H.-Y.; Wan, X.-J.; Liu, T.-Q.; Li, Y.-Q.; Yao, Y.-W. Sens. Actuators,B 2014, 200, 191.
[25] Yan, L.-R.; Yang, M.-P.; Leng, X.; Zhang, M.; Long, Y.; Yang, B.-Q. Tetrahedron 2016, 72, 4361
[26] Fan, S.-M.; Yang, W.-G.; Hao, J.-F.; Li, H.-G.; Zhao, W.-D.; Zhang, J.; Hu, Y.-H. J. Photochem. Photobiol., A 2016, 328, 129.
[27] Li, S.; Zhang, D.; Xie, X.-Y.; Ma, S.-G.; Xu, Z.-H.; Gao, Y.-F.; Ye, Y. Sens. Actuators,B 2016, 224, 661.
[28] Liu, X.-J.; Zhang, M.; Yang, M.-P.; Li, B.; Zhao, C.; Yang, B.-Q. Tetrahedron 2015, 71, 8194.
[29] Xiao, H.-F.; Zhang, M.; Liu, J.; Han, Z.-X.; Yang, L.-Q.; Wu, X.-Y. Chin. J. Org. Chem. 2016, 36, 2413(in Chinese). (肖慧丰, 张敏, 刘杰, 韩志湘, 仰榴青, 吴向阳, 有机化学, 2016, 36, 2413.)
[30] Hou, S.-H.; Qu, Z.-G.; Zhong, K.-L.; Bian, Y.-J.; Tang, L.-J. Chin. J. Org. Chem. 2016, 36, 768(in Chinese). (侯淑华, 曲忠国, 钟克利, 边延江, 汤立军, 有机化学, 2016, 36, 768).
[31] Meng, W.-F.; Yang, M.-P.; Cheng, Z.; Li, S.-N.; Yang, B.-Q. Chin. J. Org. Chem. 2014, 34, 398(in Chinese). (孟文斐, 杨美盼, 成昭, 李少妮, 杨秉勤, 有机化学, 2014, 34, 398).
[32] Wu, F.; Tian, W.-J.; Shen, J.-E. Chin. J. Lumin. 1998, 19, 158(in Chinese). (吴芳, 田文晶, 马於光, 沈家骢, 发光学报, 1998, 19, 158.)
[33] Dong, Y. Q.; Lam, J. W. Y.; Qin, A. J.; Sun, J. X.; Liu, J. Z.; Li, Z.; Sun, J. Z.; Sung, H. H. Y.; Williams, I. D.; Kwokc, H. S.; Tang, B. Z. Chem. Commun. 2007, 3255.
[34] Liu, R.-J.; Zeng, J.; Wang, H. Chin. J. Lumin. 2017, 38, 862(in Chinese). (刘瑞姣, 曾竟, 王慧, 发光学报, 2017, 38, 862.)
[35] Zhou, Z.-G.; Yu, M.-X.; Li, F.-Y. Chem. Commun. 2008, 29, 3387.
[36] Han, X.; Wang, D.-E.; Chen, S.; Zhang, L.-L.; Guo, Y.-D.; Wang, J.-Y. Anal. Methods 2015, 7, 4231.
/
| 〈 |
|
〉 |
