Citation: Wu Xiaofang, Wu Pei, Li Jingyu, Lu Jing, Wang Jianchun. Synthesis of Novel Ferrocenyl Thiazole and Imidazole Derivatives and Its Selective Recognition to Fe³⁺[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1412-1416. doi: 10.6023/cjoc201611037 shu

Synthesis of Novel Ferrocenyl Thiazole and Imidazole Derivatives and Its Selective Recognition to Fe³⁺

Department of Chemistry, Capital Normal University, Beijing 100048

Corresponding author: Wang Jianchun, cnuwjc@cnu.edu.cn
Received Date: 25 November 2016
Revised Date: 9 February 2017

Fund Project: the General Plan of Beijing Municipal Education Commission KM201710028007the Beijing Natural Science Foundation 2173060

Figures(5)

Five novel ferrocenyl thiazole and imidazole derivatives were synthesized. The structure characterization of the five products showed that ferrocene conjugative unit and thiazole or imidazole conjugative unit were linked by carbonyl methylene skeleton (COCH₂). Chloroacetylferrocene (1a) was prepared by chloroacetylation of ferrocene which reacted with different heterocyclic compounds (2-mercaptobenzothiazole, 2-mercaptobenzimidazole, imidazole and benzimidazole) to give four novel compounds, respectively. 1, 1'-Bis(bromoacetyl)ferrocene (1b) was prepared by acetylation and subsequent bromination of ferrocene, which then reacted with 2-mercaptobenzothiazole to produce 2e. All the new compounds were confirmed by ¹H NMR, ¹³C NMR, ESI-MS, HRMS and IR. Three single crystal structures were obtained. Recognition properties on 14 metal ions of the five new compounds were investigated by UV-vis spectrum. The results showed that the five new compounds possessed recognition properties only to iron(Ⅲ), in which 2a had maximum spectra response.
- ferrocene,
- thiazole,
- imidazole,
- iron(Ⅲ) ion recognition,
- tautomerism
1. [1]
  Umesh, F.; Sanjay, A.; Anil, K. Chem. Phys. Lett. 2013, 584, 165. doi: 10.1016/j.cplett.2013.08.029
2. [2]
  Choi, Y. W.; Park, G. J.; Na, Y. J.; Jo, H. Y.; Lee, S. A. You, G. R.; Kim, C. Sens. Actuators, B 2014, 194, 343. doi: 10.1016/j.snb.2013.12.114
3. [3]
  Xu, D.; Wang, M.-M.; Zeng, R.-J.; He, S.-G.; Zhang, Y.; Wang, H.; Shen, H.-T. Appl. Chem. Ind. 2013, 42, 1712 (in Chinese).
4. [4]
  Bhatt, K. D.; Makwana, B. A.; Vyas, D. J.; Mishra, D. R.; Jain, V. K. J. Lumin. 2014, 146, 450. doi: 10.1016/j.jlumin.2013.10.004
5. [5]
  Zhang, H.; Wu, X.-X.; Wu, F.-Y. Chin. J. Inorg. Chem. 2013, 29, 2394 (in Chinese).
6. [6]
  Du, B.; Ding, Z.-J.; Guo, L.; Wang, P.-H.; Li, Z.-J.; Yu, J.-H. Spectrosc. Spectral Anal. 2015, 35, 470 (in Chinese).
7. [7]
  Zhang, S.-L.; Zhao, B.; Ran, L.; Qin, D.-B.; Luo, J.-W. Chem. Reag. 2014, 36, 925 (in Chinese).
8. [8]
  Su, N.; Yang, M.-P.; Meng, W.-F.; Yang, B.-Q. Chin. J. Org. Chem. 2015, 35, 175 (in Chinese).
9. [9]
  Garcia-Beltran, O.; Cassels, B. K.; Perez, C.; Mena, N.; Nunez, M. T.; Martine, N. P.; Pavez, P.; Aliaga, M. E. Sensors 2014, 14, 1358. doi: 10.3390/s140101358
10. [10]
  Maria, A.; Arturo, E.; Alberto, T.; Pedro, M. Org. Lett. 2011, 13, 2078. doi: 10.1021/ol2004935
11. [11]
  Zapata, F.; Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. J. Org. Chem. 2009, 74, 4787. doi: 10.1021/jo900533x
12. [12]
  Caballero, A.; Lloveras, V.; Curiel, D. T.; Tarraga, A.; Espinosa, A.; Garcia, R.; Vidal-Gancedo, J.; Rovira, C.; Wurst, K.; Molina, P. Inorg. Chem. 2007, 46, 825. doi: 10.1021/ic061803b
13. [13]
  Zapata, F.; Caballero, A.; Espinosa, A.; Tarraga, A.; Molina, P. Inorg. Chem. 2009, 48, 11566. doi: 10.1021/ic901234d
14. [14]
  Romero, T.; Caballero, A.; Tárraga, A.; Molina, P. Org. Lett. 2009, 11, 3466. doi: 10.1021/ol901308z
15. [15]
  Zhuo, J.-B.; Yan, X.-Q.; Wang, X.-X.; Xie, L.-L.; Yuan, Y.-F. Chin. J. Org. Chem. 2015, 35, 1090 (in Chinese).
16. [16]
  Zhuo, J.-B., Wan, Q., Yan, X.-Q., Xie, L.-L., Yuan, Y.-F. Chem. J. Chin. Univ. 2015, 36, 477 (in Chinese).
17. [17]
  Molina, P.; Tarraga, A.; Curiel, D.; Velasco, M. D. J. Organomet. Chem. 2001, 637~639, 258.
18. [18]
  Ferreira, A. P.; Ferreira da Silva, J. L.; Duarte, M. T.; Minas da Piedade, M. F.; Robalo, M. P.; Harjivan, S. G.; Marzano, C.; Gandin, V.; Marques, M. M. Organometallics 2009, 28, 5412. doi: 10.1021/om9003835
19. [19]
  Tárraga, A.; Molina, P.; Curiel, D.; Velasco, M. D. Organometallics 2001, 20, 2145. doi: 10.1021/om000604b
1. [1]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
2. [2]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
3. [3]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
4. [4]
  Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
5. [5]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
6. [6]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
7. [7]
  Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
8. [8]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105
9. [9]
  Tong Zhou , Liyi Xie , Chuyu Liu , Xiyan Zheng , Bao Li . Between Sobriety and Intoxication: The Fascinating Journey of Sauce-Flavored Latte. University Chemistry, 2024, 39(9): 55-58. doi: 10.12461/PKU.DXHX202312048
10. [10]
  Qingjun PAN , Zhongliang GONG , Yuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365
11. [11]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
12. [12]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
13. [13]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
14. [14]
  Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105
15. [15]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
16. [16]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
17. [17]
  Xin Zhou , Zhi Zhang , Yun Yang , Shuijin Yang . A Study on the Enhancement of Photocatalytic Performance in C/Bi/Bi₂MoO₆ Composites by Ferroelectric Polarization: A Recommended Comprehensive Chemical Experiment. University Chemistry, 2024, 39(4): 296-304. doi: 10.3866/PKU.DXHX202310008
18. [18]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
19. [19]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
20. [20]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1882)
HTML views(702)

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

Synthesis of Novel Ferrocenyl Thiazole and Imidazole Derivatives and Its Selective Recognition to Fe3+

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis of Novel Ferrocenyl Thiazole and Imidazole Derivatives and Its Selective Recognition to Fe³⁺