Citation: Yi Dong, Wu Yaping, Chen Changyou, Wang Li, Wang Qin, Pu Lin, Wei Siping. Preparation of pyrido[1, 2-c][1, 2, 4]triazole-based π-conjugated triazene as a Fe³⁺ ion fluorescent sensor[J]. Chinese Chemical Letters, ;2019, 30(5): 1059-1062. doi: 10.1016/j.cclet.2019.01.013 shu

Preparation of pyrido[1, 2-c][1, 2, 4]triazole-based π-conjugated triazene as a Fe³⁺ ion fluorescent sensor

Yi Dong ^a,1 ,
Wu Yaping ^a,1 ,
Chen Changyou ^a ,
Wang Li ^a ,
Wang Qin ^a,*, ,
Pu Lin ^a,b,* ,
Wei Siping ^a,*,

a.
Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou 646000, China
b.
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, United States

Received Date: 30 October 2018
Revised Date: 25 December 2018
Accepted Date: 14 January 2019
Available Online: 15 May 2019

Figures(4)

A highly efficient coupling reaction of N-heterocyclic carbene precursors with sulfonyl azides has been developed, affording a variety of pyrido[1, 2-c][1, 2, 4]triazole-based π-conjugated triazenes. The present reaction proceeds under very mild conditions with good functional group tolerance. The resulting triazenes exhibit selective and sensitive fluorescent response toward Fe³⁺ ion.
- Triazene,
- Sulfonyl azide,
- Fluorescence,
- Iron ion,
- Sensor
1. [1]
  (a) S. Patil, A. Bugarin, Eur. J. Org. Chem. 5 (2016) 860-870;
  (b) D.B. Kimball, M.M. Haley, Angew. Chem. Int. Ed. 18 (2002) 3338-3351.
2. [2]
  (a) H. Jian, J.M. Tour, J. Org. Chem. 9(2005) 3396-3424;
  (b) M.L. Gross, D.H. Blank, W.M. Welch, J. Org. Chem. 8 (1993) 2104-2109;
  (c) E.B. Merkushev, Synthesis 12 (1988) 923-937;
  (d) G. Lunn, E.B. Sansone, L.K. Keefer, Synthesis 12 (1985) 1104-1108.
3. [3]
  (a) M.E.P. Lormann, C.H. Walker, M. Es-Sayed, et al., Chem. Commun. 12 (2002) 1296-1297;
  (b) D.B. Kimball, A.G. Hayes, M.M. Haley, Org. Lett. 24 (2000) 3825-3827;
  (c) S. Bräse, S. Dahmen, J. Heuts, Tetrahedron Lett. 34 (1999) 6201-6203.
4. [4]
  (a) K.C. Nicolaou, C.N.C. Boddy, H. Li, et al., Chem.-Eur. J. 9 (1999) 2602-2621;
  (b) W. Wirschun, G.M. Maier, J.C. Jochims, Tetrahedron 16 (1997) 5755-5766;
  (c) J.S. Moore, Acc. Chem. Res. 10 (1997) 402-413.
5. [5]
  (a) C. Hejesen, L.K. Petersen, N.J.V. Hansen, et al., Org. Biomol. Chem. 15 (2013) 2493-2497;
  (b) F. Marchesi, M. Turriziani, G. Tortorelli, et al., Pharmacol. Res. 4 (2007) 275-287.
6. [6]
  (a) E.C. Buruiana, A.L. Chibac, V. Melinte, et al., J. Chem. Sci. 1 (2013) 193-202;
  (b) E.C. Buruiana, L. Stroea, T. Buruiana, Polym. J. 41 (2009) 694;
  (c) J. Stebani, O. Nuyken, T. Lippert, et al., Die Makromol. Chem. Rapid Commun. 6 (1993) 365-369.
7. [7]
  H.E. Winberg, D.D. Coffman, J. Am. Chem. Soc. 12(1965) 2776-2777.
8. [8]
  (a) S. Patil, K. White, A. Bugarin, Tetrahedron Lett. 34 (2014) 4826-4829;
  (b) D. Jishkariani, C.D. Hall, A. Demircan, et al., J. Org. Chem. 7 (2013) 3349-3354;
  (c) D.M. Khramov, C.W. Bielawski, Chem. Commun. 39 (2005) 4958-4960.
9. [9]
  (a) Y. Ma, S. Wei, J. Lan, et al., J. Org. Chem. 73 (2008) 8256-8264;
  (b) S. Wei, B. Liu, D. Zhao, et al., Org. Biomol. Chem. 7 (2009) 4241-4247.
10. [10]
  S. Wei, S. Li, C. Chen, et al., Adv. Synth. Catal. 11(2017) 1825-1830.
11. [11]
  S.Mirlohi, A.M.Dietrich, S.E.Duncan, Environ. Sci. Technol.45(2011)6575-6583. doi: 10.1021/es200633p
12. [12]
  (a) L. Yu, Y. Qiao, L. Miao, et al., Chin. Chem. Lett. 29 (2018) 1545-1559;
  (b) T. Wang, Q. Liu, Y. Gao, et al., Chin. Chem. Lett. 27 (2016) 497-501.
1. [1]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
2. [2]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
3. [3]
  Xiangshuai Li , Jian Zhao , Li Luo , Zhuohao Jiao , Ying Shi , Shengli Hou , Bin Zhao . Visual and portable detection of metronidazole realized by metal-organic framework flexible sensor and smartphone scanning. Chinese Chemical Letters, 2024, 35(10): 109407-. doi: 10.1016/j.cclet.2023.109407
4. [4]
  Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
5. [5]
  Junqing Wu , Yiyang Zhang , Qingqing Hong , Hui Yang , Lifeng Zhang , Ming Zhang , Lei Yu . Organometallic modification of silica with europium endowing the fluorescence properties: The key technique for numerical quality monitoring. Chinese Chemical Letters, 2025, 36(4): 110165-. doi: 10.1016/j.cclet.2024.110165
6. [6]
  Erzhuo Cheng , Yunyi Li , Wei Yuan , Wei Gong , Yanjun Cai , Yuan Gu , Yong Jiang , Yu Chen , Jingxi Zhang , Guangquan Mo , Bin Yang . Galvanostatic method assembled ZIFs nanostructure as novel nanozyme for the glucose oxidation and biosensing. Chinese Chemical Letters, 2024, 35(9): 109386-. doi: 10.1016/j.cclet.2023.109386
7. [7]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
8. [8]
  Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
9. [9]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
10. [10]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
11. [11]
  Pengcheng Yan , Peng Wang , Jing Huang , Zhao Mo , Li Xu , Yun Chen , Yu Zhang , Zhichong Qi , Hui Xu , Henan Li . Engineering Multiple Optimization Strategy on Bismuth Oxyhalide Photoactive Materials for Efficient Photoelectrochemical Applications. Acta Physico-Chimica Sinica, 2025, 41(2): 100014-. doi: 10.3866/PKU.WHXB202309047
12. [12]
  Shuangying Li , Qingxiang Zhou , Zhi Li , Menghua Liu , Yanhui Li . Sensitive measurement of silver ions in environmental water samples integrating magnetic ion-imprinted solid phase extraction and carbon dot fluorescent sensor. Chinese Chemical Letters, 2024, 35(5): 108693-. doi: 10.1016/j.cclet.2023.108693
13. [13]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
14. [14]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
15. [15]
  Zehua Zhang , Haitao Yu , Yanyu Qi . 多重共振TADF分子的设计策略. Acta Physico-Chimica Sinica, 2025, 41(1): 2309042-. doi: 10.3866/PKU.WHXB202309042
16. [16]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
17. [17]
  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
18. [18]
  Xinyu Guo , Chang Li , Wenjun Deng , Yi Zhou , Yan Chen , Yushuang Xu , Rui Li . Phase engineering and heteroatom incorporation enable defect-rich MoS₂ for long life aqueous iron-ion batteries. Chinese Chemical Letters, 2025, 36(3): 109715-. doi: 10.1016/j.cclet.2024.109715
19. [19]
  Tian Cao , Xuyin Ding , Qiwen Peng , Min Zhang , Guoyue Shi . Intelligent laser-induced graphene sensor for multiplex probing catechol isomers. Chinese Chemical Letters, 2024, 35(7): 109238-. doi: 10.1016/j.cclet.2023.109238
20. [20]
  Neng Shi , Haonan Jia , Jixiang Zhang , Pengyu Lu , Chenglong Cai , Yixin Zhang , Liqiang Zhang , Nongyue He , Weiran Zhu , Yan Cai , Zhangqi Feng , Ting Wang . Accurate expression of neck motion signal by piezoelectric sensor data analysis. Chinese Chemical Letters, 2024, 35(9): 109302-. doi: 10.1016/j.cclet.2023.109302

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(758)
HTML views(4)

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

Preparation of pyrido[1, 2-c][1, 2, 4]triazole-based π-conjugated triazene as a Fe3+ ion fluorescent sensor

Metrics

通讯作者: 陈斌, bchen63@163.com

Preparation of pyrido[1, 2-c][1, 2, 4]triazole-based π-conjugated triazene as a Fe³⁺ ion fluorescent sensor