一种萘酰亚胺-罗丹明衍生物的合成、聚集诱导荧光增强及其双通道荧光探针性能

doi:10.6023/cjoc201506022

有机化学 ›› 2016, Vol. 36 ›› Issue (1): 151-157.DOI: 10.6023/cjoc201506022 上一篇下一篇

研究论文

一种萘酰亚胺-罗丹明衍生物的合成、聚集诱导荧光增强及其双通道荧光探针性能 2017-2018 Awarded

孙京府, 钱鹰

东南大学化学化工学院南京 211189

收稿日期:2015-06-17 修回日期:2015-09-06 发布日期:2015-09-17
通讯作者: 钱鹰 E-mail:yingqian@seu.edu.cn
基金资助:
国家自然科学基金(No. 61178057)资助项目.

A Novel Naphthalimide-Rhodamine Fluorescence Sensor: Synthesis, Aggregation-Induced Emission Enhancement and Its Dual-Channel Detection Property

Sun Jingfu, Qian Ying

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received:2015-06-17 Revised:2015-09-06 Published:2015-09-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 61178057).

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1. 一种萘酰亚胺-罗丹明衍生物的合成、聚集诱导荧光增强及其双通道荧光探针性能.PDF(443KB)

摘要/Abstract

合成了一种萘酰亚胺-罗丹明新型荧光探针N,N'-罗丹明内酰乙氨基-4-吡啶乙烯基-1,8-萘酰亚胺(PNRh), 并通过核磁氢谱、核磁碳谱及高分辨质谱结构表征. 测定了PNRh的固体、乙醇和水的混合溶液中的荧光光谱, 实验发现暗室中紫外灯下固体PNRh发出亮黄色荧光, 最大发射波长为592 nm. 在乙醇和水的混合溶液中, 随着含水量的增加, 荧光逐渐增强, 当含水量达到100%时, 荧光强度最大, 溶液则由微弱的蓝色荧光变为暗红色的荧光. 研究了荧光分子PNRh对金属离子Hg²⁺和Cr³⁺的选择性识别. 实验发现PNRh具有聚集诱导荧光增强的性质, 可实现对Hg²⁺和Cr³⁺的比率和双通道识别, 是一种优良的Hg²⁺和Cr³⁺检测荧光探针.

关键词: 萘酰亚胺-罗丹明, 聚集诱导荧光增强, 双通道荧光探针, Hg²⁺探针, pH探针

A novel fluorescence probe based on naphthalimide-rhodamine N,N'-rhodamine acyl ethylamino-4-pyridine vinyl-1,8-naphathlimide (PNRh) was synthesized and characterized by ¹H NMR, ¹³C NMR and HRMS techniques. Fluorescence spectra of PNRh in solid, ethanol/water mixed solution were measured. The results demonstrated that PNRh performed luminous yellow fluorescence in the solid state and the maximum emission wavelength was 592 nm. With the increasing of water content, the fluorescence intensity was enhanced in the ethanol/water mixed solution. When the water content reached 100%, the fluorescence intensity got the highest, and the color of the solution turned from slight blue fluorescence to kermesinus fluorescence. In addition, metal ion probe behavior of PNRh was detected. In a word, PNRh, possessed the characteristic of aggregation-induced emission enhancement (AIEE), was a dual-channel fluorescence sensor for detection Hg²⁺ and Cr³⁺ ions.

Key words: naphthalimide-rhodamine, aggregation-induced emission enhancement, dual-channel fluorescence probe, mercury ion fluorescence probe, pH fluorescence probe

引用此文

孙京府, 钱鹰. 一种萘酰亚胺-罗丹明衍生物的合成、聚集诱导荧光增强及其双通道荧光探针性能[J]. 有机化学, 2016, 36(1): 151-157.

Sun Jingfu, Qian Ying. A Novel Naphthalimide-Rhodamine Fluorescence Sensor: Synthesis, Aggregation-Induced Emission Enhancement and Its Dual-Channel Detection Property[J]. Chin. J. Org. Chem., 2016, 36(1): 151-157.

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[1] Ton, X. A.; Acha, V.; Bonomi, P.; Bui, B. T. S.; Haupt, K. Biosens. Bioelectron. 2015, 64, 359.
[2] Jia, T.; Fu, C.-Y.; Huang, C.-S.; Yang, H.-T.; Jia, N.-Q. ACS Appl. Mater. Interfaces 2015, 7, 10013.
[3] Li, K.-B.; Wang, H.; Zang, Y.; He, X.-P.; Li, J.; Chen, G.-R.; Tian. H. ACS Appl. Mater. Interfaces 2014, 6, 19600.
[4] Yu, C.-W.; Zhang, J.; Li, J.-H.; Liu, P.; Wei, P.-H.; Chen, L.-X. Microchim. Acta 2011, 174, 247.
[5] Tang, L.-J.; Li, F.-F.; Liu, M.-H.; Raju, N. Spectrochim. Acta, Part A 2011, 78, 1168.
[6] Quang, D. T.; Kim, J. S. Chem. Rev. 2010, 110, 6280.
[7] Seo, H.; Mi, E. J.; Ranganathan, K.; Lee, K. H.; Kim, K. T.; Lim, W.; Rhee, Y. M.; Ahn, K. H. Org. Lett. 2014, 16, 1374.
[8] Sun, S.-G.; Qiao, B.; Jiang, N.; Wang, J.-T.; Zhang, S.; Peng, X.-J. Org. Lett.2014, 16, 1132.
[9] Lou, X.-D.; Qiang, L.; Qin, J.-G.; Li, Z. ACS Appl. Mater. Interfaces 2009, 1, 2529.
[10] She, M.-Y.; Yang, Z.; Yin, B.; Zhang, J.; Gu, J.; Yin, W.-T.; Li, J.-L.; Zhao, G.-F.; Shi, Z. Dyes Pigm.2012, 92, 1337.
[11] Bao, Y.-Y.; Keersmaecker, H. D.; Corneillie, S.; Yu, F.; Mizuno, H.; Zhang, G.-F.; Hofkens, J.; Mendrek, B.; Kowalczuk, A.; Smet, M. Chem. Mater. 2015, 27, 3450.
[12] Lan, H.-C.; Wen, Y.; Shi, Y.-M.; Liu, K.-Y.; Mao, Y.-Y.; Yi, T. Analyst2014, 139, 5223.
[13] Yang, Z.; She, M.-Y.; Yin, B.; Cui, J.-H.; Zhang, Y.-Z.; Sun, W.; Li, J.-L.; Shi, Z. J. Org. Chem.2011, 77, 1143.
[14] Saha, S.; Mahato, P.; Upendar, R. G.; Suresh, E.; Chakrabarty, A.; Baidya, M.; Ghosh, S. K.; Das, A. Inorg. Chem. 2011, 51, 336.
[15] Huang K.-W.; Yang H.; Zhou Z.-G; Yu, M.-X.; Li, F.-Y.; Gao, X.; Yi, T.; Huang, C.-H. Org. Lett. 2008, 10, 2557.
[16] Fan, J.-L.; Zhan, P.; Hu, M.-M.; Sun, W.; Tang, J.-Z.; Wang, J.-Y.; Sun, S.-G.; Song, F.-L.; Peng, X.-J. Org. Lett. 2013, 15, 492.
[17] Mahato, P.; Saha, S.; Suresh, E.; Liddo, R. D.; Parnigotto, P. P.; Conconi, M. T.; Kesharwani, M. K.; Ganguly, B.; Das, A. Inorg. Chem. 2012, 51, 1769.
[18] Hu F.-Z.; Zheng, B.; Wang, D.-M.; Liu, M.-P.; Du, J.; Xiao, D. Analyst 2014, 139, 3607.
[19] Georgiev, N. I.; Asiri, A. M.; Qusti, A. H.; Alamry, K. A.; Bojinov, V. B. Dyes Pigm.2014, 102, 35.
[20] Kumar, M.; Kumar, N.; Bhalla, V.; Singh, H.; Sharma, P. R.; Kaur, T. Org. Lett. 2011, 13, 1422.
[21] Tian, Z.-Y.; Su, L.-P.; Xie, S.-Q.; Zhao, J.; Wang, C.-J. Chin. J. Org. Chem. 2013, 33, 1514 (in Chinese).(田智勇, 苏雷朋, 谢松强, 赵瑾, 王超杰, 有机化学, 2013, 33, 1514.)
[22] Zhang, F.; Tan, Z.; Yan, B.-R.; Pan, D.-W.; Bao, X.-P. Chin. J. Org. Chem. 2014, 34, 2499 (in Chinese).(张峰, 谭赞, 闫柏任, 潘顶伍, 鲍小平, 有机化学, 2014, 34, 2499.)
[23] Luo, X.-Y.; Qian, Y. Chin. J. Org. Chem. 2013, 33, 2423 (in Chinese.) (罗晓燕, 钱鹰, 有机化学, 2013, 33, 2423.)
[24] 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.)
[25] Hong, Y.-N.; Lam, J. W. Y.; Tang, B.-Z. Chem. Soc. Rev. 2011, 40, 5361.
[26] Mei, J.; Hong, Y.-N.; Lam, J. W. Y.; Qin, A.; Tang, Y.; Tang, B.-Z. Adv. Mater. 2014, 26, 5429.
[27] Zhao, Z.-J.; Lam, J. W. Y.; Tang, B.-Z. J. Mater. Chem. 2012, 22, 23726.
[28] Yu, G.; Yin, S.-W.; Liu, Y.-Q.; Chen, J.-S.; Xu, X.-J.; Sun, X.-B.; Ma, D.; Zhan, X.-W.; Peng, Q.; Shuai, Z.-G.; Tang, B.-Z.; Zhu, D.-B.; Fang, W.-W.; Luo, Y. J. Am. Chem. Soc. 2005, 127, 6335.
[29] Sun, J.-F.; Qian, Y. Chin. J. Org. Chem. 2015, 35, 1104 (in Chinese).(孙京府, 钱鹰, 有机化学, 2015, 35,1104.)
[30] Liu, Y.; Tao, X.-T.; Wang, F.-Z.; Dang, X.-N.; Zou, D.-C.; Ren, Y.; Jiang, M.-H. J. Phys. Chem. C2008, 112, 3975.
[31] Liu, Y.; Tao, X.-T.; Wang, F.-Z.; Dang, X.-N.; Zou, D.-C.; Ren, Y.; Jiang, M.-H. J. Phys. Chem. C2007, 111, 6544.
[32] Silva, A. P. D.; Gunaratne, H. Q. N.; Habib-Jiwan, J. L.; Mccoy, C. P.; Rice, T. E.; Soumillion, J. P. Angew. Chem., Int. Ed.1995, 34, 1728.
[33] Zhang, X.; Shiraishi, Y.; Hirai, T. Org. Lett. 2007, 9, 5039.

一种萘酰亚胺-罗丹明衍生物的合成、聚集诱导荧光增强及其双通道荧光探针性能 2017-2018 Awarded

A Novel Naphthalimide-Rhodamine Fluorescence Sensor: Synthesis, Aggregation-Induced Emission Enhancement and Its Dual-Channel Detection Property

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