Citation: Bing Zhao, Ya-Cui Zhou, Meng-Jiao Fan, Zhi-Yu Li, Li-Yan Wang, Qi-Gang Deng. Synthesis, fluorescence properties and selective Cr(Ⅲ) recognition of tetraaryl imidazole derivatives bearing thiazole group[J]. Chinese Chemical Letters, ;2013, 24(3): 257-259. shu

Synthesis, fluorescence properties and selective Cr(Ⅲ) recognition of tetraaryl imidazole derivatives bearing thiazole group

1.
Chemistry and Chemical Engineering Institute, Qiqihar University, Qiqihar 161006, China

Corresponding author: Bing Zhao,
Received Date: 28 November 2012
Available Online: 5 January 2013

Three tetraaryl imidazole derivatives 5a-5c bearing thiazole groups were synthesized in the presence of [Bmin]Br by one-pot reaction and their structures were fully characterized by the ¹H NMR, IR, MS and elemental analysis. The results of UV-vis spectra and fluorescent spectra upon metal ions complexation show that compound 5a displays high selectivity and sensitivity for Cr³⁺ ions. The complexation ratio of compound 5a and Cr³⁺ is 1:1.
- Tetraaryl imidazole,
- Thiazole,
- Fluorescent,
- Selectivity Cr³⁺
1. [1]
  [1] A.K. Singh, R. Singh, P. Saxena, Tetraazacyclohexadeca macrocyclic ligand as a neutral carrier in a Cr ion-selective electrode, Sensors 4 (2004) 187-195.
2. [2]
  [2] S.S.M. Hassan, M.S. EL-Shahawi, A.M. Othman, M.A. Mosaad, A potentiometric rhodamine-B based membrane sensor for the selective determination of chromium ions in wastewater, Anal. Sci. 21 (2005) 673-678.
3. [3]
  [3] (a) V. Balzani, G. Bergamini, P. Ceroni, From the photochemistry of coordination compounds to light-powered nanoscale devices and machines, Coord. Chem. Rev. 252 (2008) 2456-2469;
4. [4]
  (b) H.W. Wang, Y.Q. Feng, J.Q. Xue, A novel fluorescent calix[4]arene derivative with benzimidazole units for selective recognition to Fe, Lett. Org. Chem. 6 (2009) 409-411;
5. [5]
  (c) L.J. Fan, W.E. Jones Jr., A highly selective and sensitive inorganic/organic hybrid polymer fluorescence "turn-on" chemosensory system for iron cations, J. Am. Chem. Soc. 128 (2006) 6784-6785;
6. [6]
  (d) J. Weerasinghe, A.C. Schmiesing, E. Sinn, Highly sensitive and selective reversible sensor for the detection of Cr³⁺, Tetrahedron Lett. 50 (2009) 6407-6410;
7. [7]
  (e) J.Y. Kwon, Y.J. Jang, Y.J. Lee, et al., A highly selective fluorescent chemosensor for Pb²⁺, J. Am. Chem. Soc. 127 (2005) 10107-10111;
8. [8]
  (f) J. Huang, Y. Xu, X. Qian, A rhodamine-based Hg2+ sensor with high selectivity and sensitivity in aqueous solution: a NS₂-containing receptor, J. Org. Chem. 74 (2009) 2167-2170.
9. [9]
  [4] H. Arakawa, R.Ahmad, M. Naoui, H. Tajmir-Riahi,A comparative study of calf thymus DNA binding to Cr(Ⅲ) and Cr(Ⅵ) ions, J. Biol. Chem. 275 (2000) 10150-10153.
10. [10]
  [5] (a) M. Sarkar, S. Banthia, A. Samanta, A highly selective ‘off-on’ fluorescence chemosensor for Cr(Ⅲ), Tetrahedron Lett. 47 (2006) 7575-7578;
11. [11]
  (b) Z. Zhou, M. Yu, H. Yang, K.W. Huang, F.Y. Li, FRET-based sensor for imaging chromium(Ⅲ) in living cells, Chem. Commun. 29 (2008) 3387-3389;
12. [12]
  (c) K. Huang, H. Yang, Z. Zhou, et al., Multisignal chemosensor for Cr³⁺ and its application in bioimaging, Org. Lett. 10 (2008) 2557-2560.
13. [13]
  [6] (a) K. Kamaraj, E. Kim, B. Galliker, et al., Copper(Ⅰ) and copper(Ⅱ) complexes possessing cross-linked imidazole-phenol ligands: structures and dioxygen reactivity, J. Am. Chem. Soc. 125 (2003) 6028-6029;
14. [14]
  (b) X. Li, X. Weng, R. Tang, et al., Conformational isomerism of 1,2-bis(imidazol-1'- yl)ethane affected by the orientation of functional carboxylate groups in cadmium and cobalt helical coordination polymers, Cryst. Growth Des. 10 (2010) 3228-3236.
15. [15]
  [7] (a) N. Fridman, M. Kaftory, Y. Eichen, S. Speiser, Spectroscopy, photophysical and photochemical properties of bisimidazole derivatives, J. Photochem. Photobiol. A: Chem. 188 (2007) 25-33;
16. [16]
  (b) F. Dierschke, K. Müllen, Blue emission of a soluble poly(p-phenylene) with a cross-conjugated bisimidazole-based chromophore, Macromol. Chem. Phys. 208 (2007) 37-43;
17. [17]
  (c) M. Tsunenaga, H. Iga, M. Kimura, Location effect of an OH group on the chemiluminescence efficiency of 4-hydroperoxy-2-(o-, m-, or p-hydroxyphenyl)- 4,5-diphenyl-4H-isoimidazoles, Tetrahedron Lett. 46 (2005) 1877-1880;
18. [18]
  (d) H.G. Zhang, X.T. Tao, K.S. Chen, et al., Off-on-off luminescent switching of a dye containing imidazo[4,5-f][1,10]phenanthroline, Chin. Chem. Lett. 22 (2011) 647-650.
19. [19]
  [8] (a) H.M. Zhang, W.F. Fu, S.M. Chi, J. Wang, An asymmetric imidazole derivative as potential fluorescent chemosensor for Fe³⁺ in aqueous solution, J. Lumin. 129 (2009) 589-594;
20. [20]
  (b) N. Bian, Q. Chen, X.L. Qiu, A.D. Qi, B.H. Han, Imidazole-bearing tetraphenylethylene: fluorescent probe for metal ions based on AIE feature, New J. Chem. 35 (2011) 1667-1671.
21. [21]
  [9] Y. Suzuke, A. Bakar, T. Tanoi, N. Nomura, M. Sato, Synthesis of unsymmetrical benzils using N-heterocyclic carbene catalysis, Tetrahedron 67 (2011) 4710-4715.
1. [1]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
2. [2]
  Yi Cao , Qi Pang , Dandan Zhang , Zhengkun Xie , Jiaheng Zhang . Development of a dual-mode aptasensor platform for fluorescent and colorimetric detection of multiple targets. Chinese Chemical Letters, 2026, 37(8): 112001-. doi: 10.1016/j.cclet.2025.112001
3. [3]
  Guorong Li , Yijing Wu , Chao Zhong , Yixin Yang , Zian Lin . Predesigned covalent organic framework with sulfur coordination: Anchoring Au nanoparticles for sensitive colorimetric detection of Hg(Ⅱ). Chinese Chemical Letters, 2024, 35(5): 108904-. doi: 10.1016/j.cclet.2023.108904
4. [4]
  Xuerui Song , Xi Hu , Zhengxing Zeng , Ruikang Qin , Ting Wang , Huan Yang , Chuanfeng Wang , Zhouyu Wang , Xiaoqi Yu . White-light organic molecule based on structural regulation of aldehyde–gemdiol equilibrium and its applications in information encryption. Chinese Chemical Letters, 2026, 37(8): 112568-. doi: 10.1016/j.cclet.2026.112568
5. [5]
  Yumei Wu , Zhengjun Chen , Yuan Shen , Deying Tang , Huaiyu Mo , Zihan Chen , Hongyu Li , Zhe Zheng , Chunju Li , Jie Gao , Zeli Yuan . Water-soluble thiazolo[5,4-d]thiazole-based AIEgens for universal and Level 3 resolved latent fingerprint visualization. Chinese Chemical Letters, 2026, 37(9): 111889-. doi: 10.1016/j.cclet.2025.111889
6. [6]
  Chengyu JIANG , Xufeng LIU . Synthesis, structural characterization, electrocatalytic proton reduction, and fungicidal activity of thiazole-containing di-iron complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 355-364. doi: 10.11862/CJIC.20250253
7. [7]
  Min Hou , Yuexin Wang , Siyu Zhang , Keke Zhang , Xiu Tan , Xianjun Lang . Thiazole-linked pyrene covalent organic framework for selective sulfoxidation via an electron transfer mediator by photoredox catalysis. Chinese Chemical Letters, 2026, 37(8): 112817-. doi: 10.1016/j.cclet.2026.112817
8. [8]
  Xinyi JIAO , Xin ZHANG , Wanqiao BAI , Xuehua SUN , Huali CUI , Yixia REN , Hongmei CHAI , Loujun GAO . A Eu-based metal-organic framework fluorescent film: Preparation and sensing of Cr₂O₇^2- and tryptamine. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 1113-1120. doi: 10.11862/CJIC.20250298
9. [9]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
10. [10]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
11. [11]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
12. [12]
  Tingting Du , Siyu Lu , Dong Wang , Jian Zhang , Jixiang Chen . Recent advances of imidazole derivatives in pesticide chemistry. Chinese Chemical Letters, 2026, 37(7): 112280-. doi: 10.1016/j.cclet.2025.112280
13. [13]
  Ru Ding , Chunfei Wang , E Lv , Jingjing Zhao , Xucong Zhou , Yuanyi Li , Ying Wang , Bingxue Li , Lixia Zhang , Jin Zhou . A near-infrared fluorescent probe based on Au³⁺/Pd²⁺ complexes for glutathione sensing: Applications in acute liver injury, hepatocellular carcinoma, and ferroptosis exploration. Chinese Chemical Letters, 2025, 36(11): 111497-. doi: 10.1016/j.cclet.2025.111497
14. [14]
  Kun Song , Lijia Zhang , Yunhui Meng , Jiantong Ding , Xiaobai Li , Yongpeng Liu , Hongwei Ma . Recent development in fluorescent probes for monitoring organophosphorus pollutants. Chinese Chemical Letters, 2026, 37(5): 111902-. doi: 10.1016/j.cclet.2025.111902
15. [15]
  Jiayu Xu , Meng Li , Baoxia Dong , Ligang Feng . Fully fluorinated hybrid zeolite imidazole/Prussian blue analogs with combined advantages for efficient oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(6): 108798-. doi: 10.1016/j.cclet.2023.108798
16. [16]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
17. [17]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
18. [18]
  Ya-Ping Liu , Zhi-Rong Gui , Zhen-Wen Zhang , Sai-Kang Wang , Wei Lang , Yanzhu Liu , Qian-Yong Cao . A phenylphenthiazide anchored Tb(Ⅲ)-cyclen complex for fluorescent turn-on sensing of ClO⁻. Chinese Chemical Letters, 2025, 36(2): 109769-. doi: 10.1016/j.cclet.2024.109769
19. [19]
  Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
20. [20]
  Jiming XI , Yukang TENG , Rui ZHANG , Zhenzhong LU . Fluorescent coordination polymers based on anthracene-and pyrene-derivative ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 847-854. doi: 10.11862/CJIC.20240367

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1784)
HTML views(48)

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