Citation: Qian Chao, Chuo Luopeng, Zhao Haiying, Bian Zhanxi. Spectroscopic, Electrochemistry and Thermal Properties of Monoand 1, 1'-Disubstituted 1, 2, 3-Triazolylferrocene Derivatives[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2328-2335. doi: 10.6023/cjoc201703049 shu

Spectroscopic, Electrochemistry and Thermal Properties of Monoand 1, 1'-Disubstituted 1, 2, 3-Triazolylferrocene Derivatives

College of Chemistry and Chemical Engineering, Inner Mongolia University, Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot 010021

Corresponding author: Zhao Haiying, hyzhao@imu.edu.cn
Received Date: 29 March 2017
Revised Date: 27 April 2017
Available Online: 17 September 2017
Fund Project: Natural Science Foundation of Inner Mongolia 2013MS0207Project supported by National Natural Science Foundation of China (No. 21562032), the Research Program of Science and Technology at Universities of Inner Mongolia (No. NJZZ001) and the Natural Science Foundation of Inner Mongolia (Nos. 2013MS0207)National Natural Science Foundation of China 21562032the Research Program of Science and Technology at Universities of Inner Mongolia NJZZ001

Figures(7)

A series of mono-and 1, 1'-disubstituted 1, 2, 3-triazolylferrocene derivatives have been synthesized and characterized. In UV-Vis spectroscopy, 1, 1'-disubstituted compounds have the larger molar absorption coefficient than those of monosubstituted compounds. The fluorescence intensity weakened with increasing the number of alkoxy chain and further weakened after introduction of the highly electronegative chlorine atom. All new compounds showed quasireversible redox process. The potentials for 1, 1'-disubstituted 1, 2, 3-triazolylferrocene derivatives anodically shifted about 150 mV compared with those of monosubstituted compounds, indicating harder oxidation by loss of an electron for the former. These compounds started to decompose at about 285~305℃. The 1, 2, 3-triazolylferrocene derivative with one terminal alkoxy chain had high melting point, and suffered from degradation reaction before changing into isotropic liquid, and those with multiterminal alkoxy chains showed either simple melting and freezing process or crystal polymorphic phase to isotropic liquid phase transitions in the heating and cooling cycles.
- ferrocene,
- triazole,
- spectrum,
- electrochemistry,
- thermal behavior
1. [1]
  Navale, D. N.; Zote, S. W.; Ramana, M. M. V. J. Appl. Chem. 2015, 4, 1180.
2. [2]
  Kadkin, O. N.; Galyametdinov, Y. G. Russ. Chem. Rev. 2012, 81, 675. doi: 10.1070/RC2012v081n08ABEH004270
3. [3]
  Lim J. Y. C.; Beer P. D. Eur. J. Inorg. Chem. 2017, 220.
4. [4]
  Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. 2001, 113, 2056. doi: 10.1002/(ISSN)1521-3757
5. [5]
  Diallo, A. K.; Menuel, S.; Monflier, E.; Ruiz, J.; Astruc, D. Tetrahedron Lett. 2010, 51, 4617. doi: 10.1016/j.tetlet.2010.06.115
6. [6]
  Samanta, S.; Mittra, K.; Sengupta, K.; Chatterjee, S.; Dey, A. Inorg. Chem. 2013, 52, 1443. doi: 10.1021/ic3021782
7. [7]
  Singh, A.; Biot, C.; Viljoen, A.; Dupont, C.; Kremer, L.; Kumar, K.; Kumar, V. Chem. Biol. Drug Des. 2016, 1.
8. [8]
  Zhang, C.; Tang, J.; Yin, L.; Xi, H.; Guo, Y.; Sun, L. Chin. J. Org. Chem. 2016, 36, 358(in Chinese).
9. [9]
  Bhatta, S. R.; Bheemireddy, V.; Vijaykumar, G.; Thakur, A. Sens. Actuators, B 2017, 240, 640. doi: 10.1016/j.snb.2016.09.022
10. [10]
  Zapata, F.; Caballero, A.; Molina, P. Eur. J. Inorg. Chem. 2017, 237.
11. [11]
  Bhatta, S. R.; Bheemireddy, V.; Thakur, A. Organometallics 2017, 36, 829. doi: 10.1021/acs.organomet.6b00883
12. [12]
  Wang, Z.; Dai, B.; Qiu, J.; Cao, Q.; Ge, J. Chin. J. Org. Chem. 2015, 35, 2383(in Chinese).
13. [13]
  Cheng, H.; Ma, C.; Chen, Y.; Ni, H.; Feng, C.; Wang, B.; Zhao, K.; Yu, W.; Hu, P. Liq. Cryst. 2017, 44, 1450. doi: 10.1080/02678292.2017.1282047
14. [14]
  Zhao, H. Y.; Guo, L.; Chen, S. F.; Bian, Z. X. J. Mol. Struct. 2013, 1054~1055, 164.
15. [15]
  Zhao, H. Y.; Liu, X. Y.; Chuo. L. P.; Chen, S. F.; Bian, Z. X. J. Mol. Liq. 2015, 206, 213. doi: 10.1016/j.molliq.2015.02.031
16. [16]
  Xu, J.; Wang, S.; Li, Y.; Zhao, H.; Li, B.; Bian, Z. Chin. J. Org. Chem. 2015, 35, 1526(in Chinese).
17. [17]
  Zhao, H. Y.; Zhu, Y. Z.; Chen, C.; He, L.; Zheng, J. Y. Carbon 2012, 50, 4894. doi: 10.1016/j.carbon.2012.06.018
18. [18]
  Joubert, C. C.; van As, L.; Jakob, A.; Speck, J. M.; Lang, H.; Swarts, J. C. Polyhedron 2013, 55, 80. doi: 10.1016/j.poly.2013.02.059
19. [19]
  Kadkin, O. N.; Kim, E. H.; Kim, S. Y.; Choi, M.-G. Polyhedron 2009, 28, 1301. doi: 10.1016/j.poly.2009.01.045
20. [20]
  Kadkin, O. N.; Kim, E. H.; Rha, Y. J.; Kim, S. Y.; Tae, J.; Choi, M.-G. Chem. Eur. J. 2009, 15, 10343. doi: 10.1002/chem.v15:40
21. [21]
  Otón, F.; González, M. D. C.; Espinosa, A.; Tárraga, A.; Molina, P. Organometallics 2012, 31, 2085. doi: 10.1021/om300093c
22. [22]
  Dawson, W. R.; Windsor, M. W. J. Phys. Chem. 1968, 72, 3251. doi: 10.1021/j100855a027
1. [1]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
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]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
4. [4]
  Yongming Zhu , Huili Hu , Yuanchun Yu , Xudong Li , Peng Gao . Construction and Practice on New Form Stereoscopic Textbook of Electrochemistry for Energy Storage Science and Engineering: Taking Basic Course of Electrochemistry as an Example. University Chemistry, 2024, 39(8): 44-47. doi: 10.3866/PKU.DXHX202312086
5. [5]
  Cen Zhou , Biqiong Hong , Yiting Chen . Application of Electrochemical Techniques in Supramolecular Chemistry. University Chemistry, 2025, 40(3): 308-317. doi: 10.12461/PKU.DXHX202406086
6. [6]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
7. [7]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
8. [8]
  Linbao Zhang , Weisi Guo , Shuwen Wang , Ran Song , Ming Li . Electrochemical Oxidation of Sulfides to Sulfoxides. University Chemistry, 2024, 39(11): 204-209. doi: 10.3866/PKU.DXHX202401009
9. [9]
  Hongyi LI , Aimin WU , Liuyang ZHAO , Xinpeng LIU , Fengqin CHEN , Aikui LI , Hao HUANG . Effect of Y(PO₃)₃ double-coating modification on the electrochemical properties of Li[Ni_0.8Co_0.15Al_0.05]O₂. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1320-1328. doi: 10.11862/CJIC.20230480
10. [10]
  Yifei Cheng , Jiahui Yang , Wei Shao , Wanqun Zhang , Wanqun Hu , Weiwei Li , Kaiping Yang . Learning Goes Beyond the Written Word: Practical Insights from the “Leaf Electroplating” Popular Science Experiment. University Chemistry, 2024, 39(9): 319-327. doi: 10.3866/PKU.DXHX202310033
11. [11]
  Kuaibing Wang , Honglin Zhang , Wenjie Lu , Weihua Zhang . Experimental Design and Practice for Recycling and Nickel Content Detection from Waste Nickel-Metal Hydride Batteries. University Chemistry, 2024, 39(11): 335-341. doi: 10.12461/PKU.DXHX202403084
12. [12]
  Kuaibing Wang , Feifei Mao , Weihua Zhang , Bo Lv . Design and Practice of a Comprehensive Teaching Experiment for Preparing Biomass Carbon Dots from Rice Husk. University Chemistry, 2025, 40(5): 342-350. doi: 10.12461/PKU.DXHX202407042
13. [13]
  Zeqiu Chen , Limiao Cai , Jie Guan , Zhanyang Li , Hao Wang , Yaoguang Guo , Xingtao Xu , Likun Pan . 电容去离子提锂技术中电极材料的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100089-. doi: 10.1016/j.actphy.2025.100089
14. [14]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
15. [15]
  Jingwen Wang , Minghao Wu , Xing Zuo , Yaofeng Yuan , Yahao Wang , Xiaoshun Zhou , Jianfeng Yan . Advances in the Application of Electrochemical Regulation in Investigating the Electron Transport Properties of Single-Molecule Junctions. University Chemistry, 2025, 40(3): 291-301. doi: 10.12461/PKU.DXHX202406023
16. [16]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
17. [17]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
18. [18]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
19. [19]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1455)
HTML views(223)

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