Citation: Wang Zhonglong, Yang Jinlai, Yang Yiqin, Xu Xu, Li Mingxin, Zhang Yan, Fang Hua, Xu Haijun, Wang Shifa. Aggregation-Induced Emission-Active Fluorescent Probe for Zn²⁺ Based on Isolongifolanone and Its Application in Plant-Cell Imaging[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1401-1413. doi: 10.6023/cjoc201712009 shu

Aggregation-Induced Emission-Active Fluorescent Probe for Zn²⁺ Based on Isolongifolanone and Its Application in Plant-Cell Imaging

Wang Zhonglong ^a ,
Yang Jinlai ^b ,
Yang Yiqin ^c ,
Xu Xu ^a,e ,
Li Mingxin ^a ,
Zhang Yan ^a ,
Fang Hua ^b ,
Xu Haijun ^a,e ,
Wang Shifa ^a,e,,

a.
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
b.
Key Laboratory of High Efficient Processing of Bamboo of Zhejiang Province, China National Bamboo Research Center, Hangzhou 310012
c.
Institute of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037
d.
Department of Chemistry and Material Science, College of Science, Nanjing Forestry University, Nanjing 210037
e.
Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037

Corresponding author: Wang Shifa, wangshifa65@163.com
Received Date: 5 December 2017
Revised Date: 5 March 2018
Available Online: 16 June 2018
Fund Project: the Key Technology of Green Processing and Efficient Utilization on Oleoresin 2016YFD0600804the National Natural Science Foundation of China 31470592the University Science Research Project of Jiangsu Province 14KJ220001Project supported by the Doctorate Fellowship Foundation of Nanjing Forestry University, the National Natural Science Foundation of China (No. 31470592), the University Science Research Project of Jiangsu Province (No. 14KJ220001), the Key Technology of Green Processing and Efficient Utilization on Oleoresin (No. 2016YFD0600804)

Figures(11)

A series of hexahydroquinazolin-2-amine-based derivatives have been designed and synthesized from renewable isolongifolanone. Their solid states exhibited an enhanced emission and a dark green to bright yellow color range. In addition to good thermal stability, their solid-state fluorescence is not readily restricted by multiple conventional factors such as long term UV irradiation, increasing operated pressure and elevated heating temperature. In contrast to the derivatives which undergo serious aggregation-caused quenching (ACQ), the dimethylamino-substituted derivative 1-6, 6, 10, 10-tetramethyl-4-(4'-(N, N-dimethylamino)phenyl)-5, 7, 8, 9, 10, 10a-hexahydro-6H-6a, 9-methanobenzo[h]quinazolin-2-imino)methyl)naphthalen-2-ol (3e) demonstrate obvious aggregation-induced emission (AIE) characteristics. Moreover, these fluorescent derivatives were also used for specific and sensitive sensing of Zn²⁺ ion in aqueous solutions. Then, their photophysical mechanisms were obtained by the density functional theory calculations. These probes were successfully applied to image Zn²⁺ ion in pollen grains of Althaea rosea.
- isolongifolanone,
- aggregation-induced emission,
- aggregation-caused quenching,
- Zn²⁺ ion,
- fluorescence imaging
1. [1]
  Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. doi: 10.1021/acs.chemrev.5b00263
2. [2]
  Owens, R. M.; Malliaras, G. G. MRS Bull. 2010, 35, 449. doi: 10.1557/mrs2010.583
3. [3]
  Hong., Y.; Lam., J. W. Y.; Tang., B. Z. Chem. Soc. Rev. 2011, 40, 5361. doi: 10.1039/c1cs15113d
4. [4]
  Sekkat, N.; van den Bergh, H.; Nyokong, T.; Lange, N. Molecules 2011, 17, 98. doi: 10.3390/molecules17010098
5. [5]
  Sathiyan, G.; Sakthivel, P. Dyes Pigm. 2017, 143, 444. doi: 10.1016/j.dyepig.2017.04.065
6. [6]
  Zhang, F.; Di, Y.; Li, Y.; Qi, Q.; Qian, J.; Fu, X.; Xu, B.; Tian, W. Dyes Pigm. 2017, 142, 491. doi: 10.1016/j.dyepig.2017.04.004
7. [7]
  Chen, Y.; Bai, Y.; Han, Z.; He, W.; Guo, Z. Chem. Soc. Rev. 2015, 44, 4517. doi: 10.1039/C5CS00005J
8. [8]
  Ponnuvel, K.; Kumar, M.; Padmini, V. Sens. Actuators B:Chem. 2016, 227, 242. doi: 10.1016/j.snb.2015.12.017
9. [9]
  Ghosh, S. K.; Kim, P.; Zhang, X. A.; Yun, S. H.; Moore, A.; Lippard, S. J.; Medarova, Z. Cancer Res. 2010, 70, 6119. doi: 10.1158/0008-5472.CAN-10-1008
10. [10]
  Zhou, Y.; Kim, H. N.; Yoon, J. Bioorg. Med. Chem. Lett. 2010, 20, 125. doi: 10.1016/j.bmcl.2009.11.028
11. [11]
  Zhao, Q.; Huang, C.; Li, F. Chem. Soc. Rev. 2011, 40, 2508. doi: 10.1039/c0cs00114g
12. [12]
  Wang, S.; Li, C.; Li, J.; Chen, B.; Guo, Y. Acta Chim. Sinica 2017, 75, 383(in Chinese).
13. [13]
  Yang, L.; Liu, B.; Li, N.; Tang, B. Acta Chim. Sinica 2017, 75, 1047(in Chinese).
14. [14]
  Zhou, J.; Zhang, J.; Ren, H.; Dong, X.; Zheng, X.; Zhao, W. Chin. J. Chem. 2016, 34, 715. doi: 10.1002/cjoc.v34.7
15. [15]
  Wang, Y.; Zhao, B. Chin. J. Org. Chem. 2016, 36, 1539(in Chinese).
16. [16]
  Kimura, E.; Koike, T. Chem. Soc. Rev. 1998, 27, 179. doi: 10.1039/a827179z
17. [17]
  Falchuk, K. H. Mol. Cell. Biochem. 1998, 188, 41. doi: 10.1023/A:1006808119862
18. [18]
  Cuajungco, M. P.; Lees, G. J. Neurobiol. Dis. 1997, 4, 137. doi: 10.1006/nbdi.1997.0163
19. [19]
  Choi, D. W.; Koh, J. Y. Annu.Rev. Neurosci. 1998, 21, 347. doi: 10.1146/annurev.neuro.21.1.347
20. [20]
  Maret, W.; Jcob, C.; Vallee, B. L.; Fisher, E. H. Proc. Natil. Acad. Sci. U. S. A. 1999, 96, 1936. doi: 10.1073/pnas.96.5.1936
21. [21]
  Liu, X.; Fu, C.; Ren, X.; Liu, H.; Li, L.; Meng, X. Biosens. Bioelectron. 2015, 74, 322. doi: 10.1016/j.bios.2015.06.034
22. [22]
  Yuan, C.; Liu, X.; Wu, Y.; Lu, L.; Zhu, M. Spectrochim. Acta, Part A 2016, 154, 215. doi: 10.1016/j.saa.2015.10.035
23. [23]
  Qu, L.; Yin, C.; Huo, F.; Chao, J.; Zhang, Y.; Cheng, F. Sens. Actuators, B 2014, 191, 158. doi: 10.1016/j.snb.2013.09.114
24. [24]
  Li, N.; Xiang, Y.; Chen, X.; Tong, A. Talanta 2009, 79, 327. doi: 10.1016/j.talanta.2009.03.057
25. [25]
  Young, D. M.; Welker, J. J. C.; Doxsee, K. M. J. Chem. Educ. 2011, 88, 319. doi: 10.1021/ed1004883
26. [26]
  Vargas, F.; Rivas, C.; Medrano, M. Toxicol. Mech. Methods 2004, 14, 227. doi: 10.1080/15376520490434467
27. [27]
  Perna, G.; Palazzo, G.; Mallardi, A.; Capozzi, V. J.Lumin. 2011, 131, 1584. doi: 10.1016/j.jlumin.2011.03.055
28. [28]
  Shiraishi, Y.; Nakamura, M.; Kogure, T.; Hirai, T. New J.Chem. 2016, 40, 1237. doi: 10.1039/C5NJ02873F
29. [29]
  Orrego-Hernandez, J.; Nunez-Dallos, N.; Portilla, J. Talanta 2016, 152, 432. doi: 10.1016/j.talanta.2016.02.020
30. [30]
  Yu, S.-Y.; Hsu, C.-Y.; Chen, W.-C.; Wei, L.-F.; Wu, S.-P. Sens. Actuators, B 2014, 196, 203. doi: 10.1016/j.snb.2014.01.121
31. [31]
  Nayak, U. R.; Dev, S. Tetrahedron 1960, 8, 42. doi: 10.1016/S0040-4020(01)93329-0
32. [32]
  Jian, R.; Jianlai, Y.; Jianfeng, H.; Jiayu, W.; Xu, X.; Haijun, X.; Shifa, W. Chin. J. Org. Chem. 2016, 36, 2183(in Chinese).
33. [33]
  Kar, C.; Adhikari, M. D.; Datta, B. K.; Ramesh, A.; Das, G. Sens. Actuators, B 2013, 188, 1132. doi: 10.1016/j.snb.2013.08.005
34. [34]
  Chen, X.; Xiang, Y.; Li, Z.; Tong, A. Anal. Chim.Acta 2008, 625, 41. doi: 10.1016/j.aca.2008.07.016
35. [35]
  Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
36. [36]
  Lee, C.; Yang, W.; Parr, R. G. Physic. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785
1. [1]
  Yue WANG , Zhizhi GU , Jingyi DONG , Jie ZHU , Cunguang LIU , Guohan LI , Meichen LU , Jian HAN , Shengnan CAO , Wei WANG . Effects of kelp-derived carbon dots on embryonic development of zebrafish. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1209-1217. doi: 10.11862/CJIC.20230423
2. [2]
  Jun-Jie Fang , Zheng Liu , Yun-Peng Xie , Xing Lu . Superatomic Ag₅₈ nanoclusters incorporating a [MS₄@Ag₁₂]²⁺ (M = Mo or W) kernel show aggregation-induced emission. Chinese Chemical Letters, 2024, 35(10): 109345-. doi: 10.1016/j.cclet.2023.109345
3. [3]
  Yunli Xu , Xuwen Da , Lei Wang , Yatong Peng , Wanpeng Zhou , Xiulian Liu , Yao Wu , Wentao Wang , Xuesong Wang , Qianxiong Zhou . Ru(Ⅱ)-based aggregation-induced emission (AIE) agents with efficient ¹O₂ generation, photo-catalytic NADH oxidation and anticancer activity. Chinese Chemical Letters, 2025, 36(5): 110168-. doi: 10.1016/j.cclet.2024.110168
4. [4]
  Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma . Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine. Chinese Chemical Letters, 2024, 35(11): 109791-. doi: 10.1016/j.cclet.2024.109791
5. [5]
  Tong-Tong Zhou , Guan-Yu Ding , Xue Li , Li-Li Wen , Xiao-Xu Pang , Ying-Chen Duan , Ju-Yang He , Guo-Gang Shan , Zhong-Min Su . Design of near-infrared aggregation-induced emission photosensitizers by π-bridge engineering for boosting theranostic efficacy. Chinese Chemical Letters, 2025, 36(6): 110341-. doi: 10.1016/j.cclet.2024.110341
6. [6]
  Min Liu , Bin Feng , Feiyi Chu , Duoyang Fan , Fan Zheng , Fei Chen , Wenbin Zeng . An ESIPT-boosted NIR nanoprobe for ratiometric sensing of carbon monoxide via activatable aggregation-induced dual-color fluorescence. Chinese Chemical Letters, 2025, 36(5): 110043-. doi: 10.1016/j.cclet.2024.110043
7. [7]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
8. [8]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
9. [9]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
10. [10]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
11. [11]
  Ze Wang , Hao Liang , Annan Liu , Xingchen Li , Lin Guan , Lei Li , Liang He , Andrew K. Whittaker , Bai Yang , Quan Lin . Strength through unity: Alkaline phosphatase-responsive AIEgen nanoprobe for aggregation-enhanced multi-mode imaging and photothermal therapy of metastatic prostate cancer. Chinese Chemical Letters, 2025, 36(2): 109765-. doi: 10.1016/j.cclet.2024.109765
12. [12]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
13. [13]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
14. [14]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747
15. [15]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
16. [16]
  Peide Zhu , Yangjia Liu , Yaoyao Tang , Siqi Zhu , Xinyang Liu , Lei Yin , Quan Liu , Zhiqiang Yu , Quan Xu , Dixian Luo , Juncheng Wang . Bi-doped carbon quantum dots functionalized liposomes with fluorescence visualization imaging for tumor diagnosis and treatment. Chinese Chemical Letters, 2024, 35(4): 108689-. doi: 10.1016/j.cclet.2023.108689
17. [17]
  Biao Huang , Tao Tang , Fushou Liu , Shi-Hui Chen , Zhi-Ling Zhang , Mingxi Zhang , Ran Cui . Quantum dots boost large-view NIR-Ⅱ imaging with high fidelity for fluorescence-guided tumor surgery. Chinese Chemical Letters, 2024, 35(12): 109694-. doi: 10.1016/j.cclet.2024.109694
18. [18]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
19. [19]
  Zhoupeng Zheng , Shengyi Gong , Qianhua Li , Shiya Zhang , Guoqiang Feng . Lipid droplets and gallbladder targeted fluorescence probe for ratiometric NO imaging in gallstones disease models. Chinese Chemical Letters, 2025, 36(5): 110191-. doi: 10.1016/j.cclet.2024.110191
20. [20]
  Ziyou Zhang , Te Ji , Hongliang Dong , Zhiqiang Chen , Zhi Su . Effect of coordination restriction on pressure-induced fluorescence evolution. Chinese Chemical Letters, 2024, 35(12): 109542-. doi: 10.1016/j.cclet.2024.109542

Get Citation

PDF

XML

Metrics

PDF Downloads(19)
Abstract views(1529)
HTML views(238)

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

Aggregation-Induced Emission-Active Fluorescent Probe for Zn2+ Based on Isolongifolanone and Its Application in Plant-Cell Imaging

Metrics

通讯作者: 陈斌, bchen63@163.com

Aggregation-Induced Emission-Active Fluorescent Probe for Zn²⁺ Based on Isolongifolanone and Its Application in Plant-Cell Imaging