Citation: Sun Jingfu, Qian Ying. A Novel Naphthalimide-Rhodamine Fluorescence Sensor: Synthesis, Aggregation-Induced Emission Enhancement and Its Dual-Channel Detection Property[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 151-157. doi: 10.6023/cjoc201506022 shu

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

Sun Jingfu ,
Qian Ying ^*,,

1.
School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Corresponding author: Qian Ying, yingqian@seu.edu.cn
Received Date: 17 June 2015
Revised Date: 6 September 2015

Fund Project: the National Natural Science Foundation of China 61178057

Figures(8)

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.
- naphthalimide-rhodamine,
- aggregation-induced emission enhancement,
- dual-channel fluorescence probe,
- mercury ion fluorescence probe,
- pH fluorescence probe
1. [1]
  Ton, X. A.; Acha, V.; Bonomi, P.; Bui, B. T. S.; Haupt, K. Biosens. Bioelectron. 2015, 64, 359. doi: 10.1016/j.bios.2014.09.017
2. [2]
  Jia, T.; Fu, C.-Y.; Huang, C.-S.; Yang, H.-T.; Jia, N.-Q. ACS Appl. Mater. Interfaces 2015, 7, 10013. doi: 10.1021/acsami.5b02429
3. [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. doi: 10.1021/am505435s
4. [4]
  Yu, C.-W.; Zhang, J.; Li, J.-H.; Liu, P.; Wei, P.-H.; Chen, L.-X. Microchim. Acta 2011, 174, 247. doi: 10.1007/s00604-011-0623-2
5. [5]
  Tang, L.-J.; Li, F.-F.; Liu, M.-H.; Raju, N. Spectrochim. Acta, Part A 2011, 78, 1168. doi: 10.1016/j.saa.2010.12.072
6. [6]
  Quang, D. T.; Kim, J. S. Chem. Rev. 2010, 110, 6280. doi: 10.1021/cr100154p
7. [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. doi: 10.1021/ol5001389
8. [8]
  Sun, S.-G.; Qiao, B.; Jiang, N.; Wang, J.-T.; Zhang, S.; Peng, X.-J. Org. Lett.2014, 16, 1132. doi: 10.1021/ol500284p
9. [9]
  Lou, X.-D.; Qiang, L.; Qin, J.-G.; Li, Z. ACS Appl. Mater. Interfaces 2009, 1, 2529. doi: 10.1021/am900467b
10. [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. doi: 10.1016/j.dyepig.2011.09.014
11. [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. doi: 10.1021/acs.chemmater.5b00858
12. [12]
  Lan, H.-C.; Wen, Y.; Shi, Y.-M.; Liu, K.-Y.; Mao, Y.-Y.; Yi, T. Analyst2014, 139, 5223. doi: 10.1039/C4AN01014K
13. [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. [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. [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. doi: 10.1021/ol800778a
16. [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. doi: 10.1021/ol3032889
17. [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. doi: 10.1021/ic202073q
18. [18]
  Hu F.-Z.; Zheng, B.; Wang, D.-M.; Liu, M.-P.; Du, J.; Xiao, D. Analyst 2014, 139, 3607. doi: 10.1039/c4an00303a
19. [19]
  Georgiev, N. I.; Asiri, A. M.; Qusti, A. H.; Alamry, K. A.; Bojinov, V. B. Dyes Pigm.2014, 102, 35. doi: 10.1016/j.dyepig.2013.10.007
20. [20]
  Kumar, M.; Kumar, N.; Bhalla, V.; Singh, H.; Sharma, P. R.; Kaur, T. Org. Lett. 2011, 13, 1422. doi: 10.1021/ol2001073
21. [21]
  Tian, Z.-Y.; Su, L.-P.; Xie, S.-Q.; Zhao, J.; Wang, C.-J.Chin. J. Org. Chem. 2013, 33, 1514 (in Chinese). doi: 10.6023/cjoc201301008
22. [22]
  Zhang, F.; Tan, Z.; Yan, B.-R.; Pan, D.-W.; Bao, X.-P. Chin. J. Org. Chem. 2014, 34, 2499 (in Chinese). doi: 10.6023/cjoc201407012
23. [23]
  Luo, X.-Y.; Qian, Y. Chin. J. Org. Chem. 2013, 33, 2423 (in Chinese.) doi: 10.6023/cjoc201305034
24. [24]
  Meng, W.-F.; Yang, M.-P.; Cheng, Z.; Li, S.-N.; Yang, B.-Q. Chin. J. Org. Chem. 2014, 34, 398 (in Chinese). doi: 10.6023/cjoc201307039
25. [25]
  Hong, Y.-N.; Lam, J. W. Y.; Tang, B.-Z. Chem. Soc. Rev. 2011, 40, 5361. doi: 10.1039/c1cs15113d
26. [26]
  Mei, J.; Hong, Y.-N.; Lam, J. W. Y.; Qin, A.; Tang, Y.; Tang, B.-Z. Adv. Mater. 2014, 26, 5429. doi: 10.1002/adma.201401356
27. [27]
  Zhao, Z.-J.; Lam, J. W. Y.; Tang, B.-Z. J. Mater. Chem. 2012, 22, 23726. doi: 10.1039/c2jm31949g
28. [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. doi: 10.1021/ja044628b
29. [29]
  Sun, J.-F.; Qian, Y. Chin. J. Org. Chem. 2015, 35, 1104 (in Chinese). doi: 10.6023/cjoc201411008
30. [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. doi: 10.1021/jp7117373
31. [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. [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. doi: 10.1002/(ISSN)1521-3773
33. [33]
  Zhang, X.; Shiraishi, Y.; Hirai, T. Org. Lett. 2007, 9, 5039. doi: 10.1021/ol7022714
1. [1]
  Mi Wen , Baoshuo Jia , Yongqi Chai , Tong Wang , Jianbo Liu , Hailong Wu . Improvement of Fluorescence Quantitative Analysis Experiment: Simultaneous Determination of Rhodamine 6G and Rhodamine 123 in Food Using Chemometrics-Assisted Three-Dimensional Fluorescence Method. University Chemistry, 2025, 40(4): 390-398. doi: 10.12461/PKU.DXHX202405147
2. [2]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
3. [3]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
4. [4]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
5. [5]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
6. [6]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
7. [7]
  Yang Xia , Kangyan Zhang , Heng Yang , Lijuan Shi , Qun Yi . 构建双通道路径增强iCOF/Bi₂O₃ S型异质结在纯水体系中光催化合成H₂O₂性能. Acta Physico-Chimica Sinica, 2024, 40(11): 2407012-. doi: 10.3866/PKU.WHXB202407012
8. [8]
  Pingping LU , Shuguang ZHANG , Peipei ZHANG , Aiyun NI . Preparation of zinc sulfate open frameworks based probe materials and detection of Pb²⁺ and Fe³⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 959-968. doi: 10.11862/CJIC.20240411
9. [9]
  Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
10. [10]
  Yang Wang , Yunpeng Fu , Xiaoji Liu , Guotao Zhang , Guobin Li , Wanqiang Liu , Jinglun Wang . Structural Analysis of Nitrile Solutions Based on Infrared Spectroscopy Probes. University Chemistry, 2025, 40(4): 367-374. doi: 10.12461/PKU.DXHX202406113
11. [11]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
12. [12]
  Jie Zhou , Chuanxiang Zhang , Changchun Hu , Shuo Li , Yuan Liu , Zhu Chen , Song Li , Hui Chen , Rokayya Sami , Yan Deng . Electrochemical aptasensor based on black phosphorus-porous graphene nanocomposites for high-performance detection of Hg²⁺. Chinese Chemical Letters, 2024, 35(11): 109561-. doi: 10.1016/j.cclet.2024.109561
13. [13]
  Xia ZHANG , Yushi BAI , Xi CHANG , Han ZHANG , Haoyu ZHANG , Liman PENG , Shushu HUANG . Preparation and photocatalytic degradation performance of rhodamine B of BiOCl/polyaniline. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 913-922. doi: 10.11862/CJIC.20240255
14. [14]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
15. [15]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
16. [16]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
17. [17]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
18. [18]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
19. [19]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
20. [20]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1606)
HTML views(221)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142