Citation: Zhou Chan, Qiu Bo, Zeng Yi, Chen Jinping, Yu Tianjun, Li Yi. A Reaction-Based Chemsensor for Hydrogen Sulfide Detection with Fluorescence Enhancement[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 92-96. doi: 10.6023/cjoc201607034 shu

A Reaction-Based Chemsensor for Hydrogen Sulfide Detection with Fluorescence Enhancement

Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Corresponding author: Zeng Yi, zengyi@mail.ipc.ac.cn Li Yi, yili@mail.ipc.ac.cn
Received Date: 20 July 2016
Revised Date: 8 October 2016

Fund Project: the the National Natural Science Foundation of China 21233011the State Key Development Program for Basic Research of China 2013CB834505the State Key Development Program for Basic Research of China 973 Programthe State Key Development Program for Basic Research of China 2013CB834703

Figures(4)

A reaction-based probe 8-(2, 4-dinitrophenoxy) pyrene-1-carbaldehyde (PCNP) for H₂S detection was designed and synthesized by utilizing 8-hydroxypyrene-1-carbaldehyde and dinitrophenyl ether as the reporting chromophore and the recognition unit, respectively.The probe was dissolved in phosphate buffer saline (PBS) with cetyltrimethyl ammonium bromide (CTAB), and the sensing ability toward H₂S was investigated with steady-state spectroscopy.The emission of PCNP was quenched by photoinduced electron transfer without H₂S.The fluorescence of PCNP was boosted after thiolysis reaction in the presence of H₂S, showing orange red emission.The fluorescence response was rapid and reached a maximum enhancement of about 260 times in the presence of 0.1 mmol·L^-1 H₂S, giving a reaction rate constant of 0.20 min^-1.The limit of detection of PCNP is estimated to be 0.10 μmol·L^-1.The results demonstrate that PCNP is capable of detecting H₂S rapidly, sensitively and selectively.
- fluorescent sensor,
- reaction-based sensor,
- thiolysis reaction,
- fluorescence enhancement,
- hydrogen sulfide
1. [1]
  Lin, V. S.; Chen, W.; Xian, M.; Chang, C. J. Chem. Soc. Rev. 2015, 44, 4596. doi: 10.1039/C4CS00298A
2. [2]
  Kimura, H. Antioxid. Redox Signaling 2014, 20, 783. doi: 10.1089/ars.2013.5309
3. [3]
  Paul, B. D.; Sbodio, J. I.; Xu, R. S.; Vandiver, M. S.; Cha, J. Y.; Snowman, A. M.; Snyder, S. H. Nature 2014, 509, 96. doi: 10.1038/nature13136
4. [4]
  Hu, L. F.; Lu, M.; Tiong, C. X.; Dawe, G. S.; Hu, G.; Bian, J. S. Aging Cell 2010, 9, 135. doi: 10.1111/ace.2010.9.issue-2
5. [5]
  Giuliani, D.; Ottani, A.; Zaffe, D.; Galantucci, M.; Strinati, F.; Lodi, R.; Guarini, S. Neurobiol. Learn. Mem. 2013, 104, 82. doi: 10.1016/j.nlm.2013.05.006
6. [6]
  Gao, M.; Yu, F. B.; Chen, L. X. Prog. Chem. 2014, 26, 1065 (in Chinese).
7. [7]
  Qian, Y.; Karpus, J.; Kabil, O.; Zhang, S. Y.; Zhu, H. L.; Banerjee, R.; Zhao, J.; He, C. Nat. Commun. 2011, 2, 495. doi: 10.1038/ncomms1506
8. [8]
  Peng, B.; Chen, W.; Liu, C. R.; Rosser, E. W.; Pacheco, A.; Zhao, Y.; Aguilar, H. C.; Xian, M. Chem.-Eur. J. 2014, 20, 1010. doi: 10.1002/chem.201303757
9. [9]
  Yu, H. B.; Li, H. L.; Zhang, X. F.; Xiao, Y.; Fang, P. J.; Lv, C. J.; Hou, W. Acta Chim. Sinica 2015, 73, 450 (in Chinese). doi: 10.6023/A15030158
10. [10]
  Zhao, C. C.; Zhang, X. L.; Li, K. B.; Zhu, S. J.; Guo, Z. Q.; Zhang, L. L.; Wang, F. Y.; Fei, Q.; Luo, S. H.; Shi, P.; Tian, H.; Zhu, W. H. J. Am. Chem. Soc. 2015, 137, 8490. doi: 10.1021/jacs.5b03248
11. [11]
  Lippert, A. R.; New, E. J.; Chang, C. J. J. Am. Chem. Soc. 2011, 133, 10078. doi: 10.1021/ja203661j
12. [12]
  Zheng, Y.; Zhao, M.; Qiao, Q. L.; Liu, H. Y.; Lang, H. J.; Xu, Z. C.Dyes Pigm. 2013, 98, 367. doi: 10.1016/j.dyepig.2013.03.014
13. [13]
  Sun, W.; Fan, J. L.; Hu, C.; Cao, J. F.; Zhang, H.; Xiong, X. Q.; Wang, J. Y.; Cui, S.; Sun, S. G.; Peng, X. J. Chem. Commun. 2013, 49, 3890. doi: 10.1039/c3cc41244j
14. [14]
  Fan, F. L.; Jing, J. Q.; Chen, X. M. Chin. J. Org. Chem. 2014, 34, 2178 (in Chinese). doi: 10.6023/cjoc201404015
15. [15]
  Sasakura, K.; Hanaoka, K.; Shibuya, N.; Mikami, Y.; Kimura, Y.; Komatsu, T.; Ueno, T.; Terai, T.; Kimura, H.; Naganot, T. J. Am. Chem. Soc. 2011, 133, 18003. doi: 10.1021/ja207851s
16. [16]
  Qu, X. Y.; Li, C. J.; Chen, H. C.; Mack, J.; Guo, Z. J.; Shen, Z. Chem. Commun. 2013, 49, 7510. doi: 10.1039/c3cc44128h
17. [17]
  Liu, J.; Guo, X. D.; Hu, R.; Liu, X. Y.; Wang, S. Q.; Li, S. Y.; Li, Y.; Yang, G. Q. Anal. Chem. 2016, 88, 1052. doi: 10.1021/acs.analchem.5b04248
18. [18]
  Fridkin, M.; Hazum, E.; Tauberfinkelstein, M.; Shaltiel, S. Arch. Biochem. Biophys. 1977, 178, 517. doi: 10.1016/0003-9861(77)90222-3
19. [19]
  Liu, T. Y.; Xu, Z. C.; Spring, D. R.; Cui, J. N. Org. Lett. 2013, 15, 2310. doi: 10.1021/ol400973v
20. [20]
  Yuan, L.; Zuo, Q. P. Sens. Actuators, B 2014, 196, 151. doi: 10.1016/j.snb.2014.01.118
21. [21]
  Liu, Y.; Feng, G. Q. Org. Biomol. Chem. 2014, 12, 438. doi: 10.1039/C3OB42052C
22. [22]
  Cao, L. X.; Li, X. Y.; Wang, S. Q.; Li, S. Y.; Li, Y.; Yang, G. Q. Chem. Commun. 2014, 50, 8787. doi: 10.1039/C4CC03716B
23. [23]
  Qiu, B.; Zeng, Y.; Cao, L. X.; Hu, R.; Zhang, X. H.; Yu, T. J.; Chen, J. P.; Yang, G. Q.; Li, Y. RSC Adv. 2016, 6, 49158. doi: 10.1039/C6RA04747E
1. [1]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
2. [2]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
3. [3]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
4. [4]
  Xingyu Liao , Xiangming Yi , Kin Shing Chan . 追凶之路上的怪客——硫化氢. University Chemistry, 2025, 40(6): 172-176. doi: 10.12461/PKU.DXHX202408039
5. [5]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
6. [6]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
7. [7]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
8. [8]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
9. [9]
  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
10. [10]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
11. [11]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
12. [12]
  Yiming Liang , Ziyan Pan , Kin Shing Chan . One Drink, Two Tears in the Central Nervous System: The Perils of Disulfiram-Like Reactions. University Chemistry, 2025, 40(4): 322-325. doi: 10.12461/PKU.DXHX202406016
13. [13]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
14. [14]
  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
15. [15]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
16. [16]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394
17. [17]
  Wei GAO , Meiqi SONG , Xuan REN , Jianliang BAI , Jing SU , Jianlong MA , Zhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112
18. [18]
  Lei ZHANG , Cheng HE , Yang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081
19. [19]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
20. [20]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052

Get Citation

PDF

XML

Metrics

PDF Downloads(31)
Abstract views(3172)
HTML views(729)

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