Citation: QIN A-Hui, GONG Shuai, ZHANG Yan, GAO Yu, WANG Zhong-Long, WANG Shi-Fa. A Novel Isolongifolanylindazole Derivatives Colorimetric Probe for Naked-eye Detection of H₂S in Water Environment[J]. Chinese Journal of Analytical Chemistry, ;2021, 49(11): 1845-1854. doi: 10.19756/j.issn.0253-3820.210449 shu

A Novel Isolongifolanylindazole Derivatives Colorimetric Probe for Naked-eye Detection of H₂S in Water Environment

QIN A-Hui ² ,
GONG Shuai ² ,
ZHANG Yan ² ,
GAO Yu ² ,
WANG Zhong-Long ² ,
WANG Shi-Fa ^1,2,,

1.
Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China;
2.
College of Chemical-Engineering, Nanjing Forestry University, Nanjing 210037, China

Corresponding author: WANG Shi-Fa, wangshifa65@163.com
Received Date: 19 April 2021
Revised Date: 14 July 2021

Fund Project: Supported by the National Natural Science Foundation of China (No.32071707).

Hydrogen sulfide (H₂S) plays crucial roles in various physiological process and daily life. However, excess H₂S is very harmful to health. Therefore, it is necessary to design a sensitive method for H₂S detection.In this work, a novel colorimetric probe 5,5,9,9-tetramethyl-3-(4-nitrophenyl)-2,4,5,6,7,8,9,9a-octahydro-5a,8-methanobenzo[g]indazole (BN) for naked-eye detection of H₂S was developed with longifolene derivative isolongifolenone as the starting material. This probe had great merits including rapid response time (0.4 min), high sensitivity (detection limit of 0.31 μmol/L), and high selectivity for H₂S detection. The sensing mechanism was confirmed by ¹H NMR and HRMS. The experiment results showed that the -NO₂ group was reduced into -NH₂ group by H₂S, and the hydrogen atom on the indazole ring disappeared as soon as probe BN contacted with H₂S. The photophysical properties of probe BN toward H₂S were examined by density functional theory calculation. Additionally, the probe BN could be loaded on filter paper and was successfully applied to detection of H₂S in environmental water samples.
- Isolongifolenone,
- Indazole derivatives,
- Colorimetric probe,
- Hydrogen sulfide
1. [1]
  LANTTO V, MIZSEI J. Sens. Actuators, B, 1991, 5(1-4):21-25.
2. [2]
  XU T L, SCAFA N, XU L P, ZHOU S F, ABDULLAHK A, MAHBOOB S, FUGETSU B, ZHANG X J. Analyst, 2016, 141(4):1185-1195.
3. [3]
  WALLACE J L, WANG R. Nat. Rev. Drug Discov., 2015, 14(5):329-345.
4. [4]
  ANDRUSK B, MCCAFFERTY D M, IGNACY T, MILLEN B, MCDOUGALLJ J. Am. J. Physiol. Regul. Integr. Comp. Physiol., 2008, 295(3):814-820.
5. [5]
  CHEN Y H, WANG P P, WANG X M, HE Y J, YAO W Z, QI Y F, TANG C S. Cytokine, 2011, 53(3):334-341.
6. [6]
  WANG R, FAN Q, ZHANG J, KANG Y, WANG Z. Transl. Oncol., 2018, 11(4):900-910.
7. [7]
  HELLMICH M R, SZABO C. Handb. Exp. Pharmacol., 2015, 230:233-241.
8. [8]
  LEE Z W, ZHOU J, CHEN C S, ZHAO Y, TAN C H, LI L, MOORE P K, DENG L W. PloS One, 2011, 6(6):21077.
9. [9]
  WANG M, ZHU J, PAN Y, DONG J, ZHANG L, ZHANG X, ZHANG L. J. Neurosci. Res., 2015, 93(3):487-494.
10. [10]
  FERNANDES V S, XIN W, PETKOV G V. Am. J. Physiol. Cell Physiol., 2015, 309(2):107-116.
11. [11]
  KULKARNI K H, MONJOK E M, ZEYSSIG R, BONGMBA O N, OPERE C A, NJIE Y F, OHIA S E. Neurochem. Res., 2009, 34(3):400-406.
12. [12]
  XUE R, HAO D D, SUN J P, LI W W, ZHAO M M, LI X H, CHEN Y, ZHU J H, DING Y J, LIU J, ZHU Y C. Antioxid. Redox. Signal., 2013, 19(1):5-23.
13. [13]
  HU N, DONG M, REN J. Am. J. Physiol. Regul. Integr. Comp. Physiol., 2014, 306(10):761-771.
14. [14]
  DU Z, SONG B, ZHANG W, DUAN C, WANG Y L, LIU C, ZHANG R, YUAN J. Angew. Chem., Int. Ed., 2018, 57(15):3999-4004.
15. [15]
  WU M Y, LI K, HOU J T, HUANG Z, YU X Q. Org. Biomol. Chem., 2012, 10(41):8342-8347.
16. [16]
  UBUKA T. J. Chromatogr. B, 2002, 781(1):227-249.
17. [17]
  FURNE J, SAEED A, LEVITT M D. Am. J. Physiol. Regul. Integr. Comp. Physiol., 2008, 295(5):1479-1485.
18. [18]
  TAYLOR H E, GIBSON J H, SKOGERBOE R K. Annu. Rev. Anal. Chem. (Palo Alto Calif)., 1970, 42(13):1569-1575.
19. [19]
  MONNOT M, NOGUEIRAR P, ROCHE V, BERTHOME G, CHAUVEAU E, ESTEVEZ R, MANTEL M. Appl. Surf. Sci., 2017, 394(1):132-141.
20. [20]
  KNAERY J R, CUTTER G A. Anal. Chem., 1993, 65(8):976-982.
21. [21]
  CUTTER G A, OATTS T J. Anal. Chem., 1987, 59(5):717-721.
22. [22]
  PANDEY S K, KIM K Y. Environ. Sci. Technol., 2009, 43(9):3020-3029.
23. [23]
  PANDEY S K, KIM K H, TANG K T. TrAC-Trends Anal. Chem., 2012, 32:87-99.
24. [24]
25. [25]
  LAWRENCE N S, DEO R P, WANG J. Anal. Chim. Acta, 2004, 517(1):131-137.
26. [26]
  LAWRENCE N S, DAVIS J, JIANG L, JONES T G J, DAVIES S N, COMPTON R G. Electroanalysis, 2000, 12(18):1453-1460.
27. [27]
  LIN V S, LIPPERT A R, CHANG C J. Proc. Natl. Acad. Sci. U. S. A., 2013, 110(18):7131-7135.
28. [28]
  RAJASWATHI K, JAYANTHI M, RAJMOHAN R, ANBAZHAGAN V, VAIRAKASH P. Spectrochim. Acta, Part A, 2019, 212:308-314.
29. [29]
  WEI C, ZHU Q, LIU W, CHEN W, XI Z, YI L. Org. Biomol. Chem., 2014, 12(3):479-485.
30. [30]
  ZHAO Y, ZHU X, KAN H, WANG W, ZHU B, DU B, ZHANG X. Analyst, 2012, 137(23):5576-5580.
31. [31]
  ZHANG D, JIN W. Spectrochim. Acta, Part A, 2012, 90:35-39.
32. [32]
  XIANG K, LIU Y, LI C, TIAN B, TONG T, ZHANG J. Dyes Pigm., 2015, 123:78-84.
33. [33]
  LOU T, CHEN Z, WANG Y, CHEN L. J. Am. Chem. Soc., 2011, 3(5):1568-1573.
34. [34]
  KAUR P, SAREEN D, SINGH K. Talanta, 2011, 83(5):1695-1700.
35. [35]
  HE L W, YANG X L, LIU Y, LIN W Y. Anal. Methods, 2016, 8:8022-8027.
36. [36]
  YANG Y, LIU Y U, YANG L, LIU J, LI K, LUO S. J. Chem. Sci., 2015, 127(3):359-363.
37. [37]
  LIU Y, FENG G. Org. Biomol. Chem., 2013, 12(3):438-445.
38. [38]
  KAUSHIK R, GHOSH A, SINGH A, JOSE D A. Anal. Chim. Acta, 2018, 1040:177-186.
39. [39]
  WANG Z, YANG J, YANG Y, FANG H, XU X, RUI J, SU F, XU H, WANG S. RSC Adv., 2017, 7(53):33263-33272.
40. [40]
41. [41]
  ABHISHEK K J, ANKUR V, VEERESAMY R, KASHAW S K, AGRAWAL R K. Bioorg. Med. Chem., 2012, 20(11):3378-3395.
42. [42]
  SALMAN A K, MOHAMMED Y. Eur. J. Med. Chem., 2008, 44(6):2597-2600.
43. [43]
  AMIT V, SHAILENDRA K S. Eur. J. Med. Chem., 2008, 43(5):897-905.
44. [44]
  WANG Z, ZHANG Y, LI M, YANG Y, XU X, XU H, LIU J, FANG H, WANG S. Tetrahedron, 2018, 74(24):3030-3037.
45. [45]
  WANG Z, ZHANG Y, SONG J, LI M, YANG Y, XU X, XU H, WANG S. Sens. Actuators, B, 2020, 304:127083.
46. [46]
  WANG Z, YANG J, LIU P, YANG Y, FANG H, XU X, RUI J, XU H, WANG S. Tetrahedron, 2017, 73(40):5912-5919.
47. [47]
  WANG Z, ZHANG Y, SONG J, YANG Y, XU X, LI M, XU H, WANG S. Anal. Chim. Acta, 2019, 1051:169-178.
48. [48]
  KUMAR N, BHALLA V, KUMAR M. Coord. Chem. Rev., 2013, 257(15):2335-2347.
49. [49]
  LI J F, YIN C X, HUO F J. RSC Adv., 2015, 5(3):2191-2206.
50. [50]
  LEE C, YANG W, PARR R G. Phys. Rev. B, 1988, 37:785-789.
51. [51]
  WANG Y, CHENG X L, YANG X D, YANG X. J. Solution Chem., 2006, 35:869-878.
1. [1]
  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
2. [2]
  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
3. [3]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 100027-0. doi: 10.3866/PKU.WHXB202406007
4. [4]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
5. [5]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
6. [6]
  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
7. [7]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
8. [8]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
9. [9]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
10. [10]
  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
11. [11]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
12. [12]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
13. [13]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
14. [14]
  Zhicheng JU , Wenxuan FU , Baoyan WANG , Ao LUO , Jiangmin JIANG , Yueli SHI , Yongli CUI . MOF-derived nickel-cobalt bimetallic sulfide microspheres coated by carbon: Preparation and long cycling performance for sodium storage. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 661-674. doi: 10.11862/CJIC.20240363
15. [15]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
16. [16]
  Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
17. [17]
  Renyi Shao , Khurram Abbas , Vladimir Yu. Osipov , Haimei Zhu , Yuan Li , Usama , Hong Bi . Red-emitting carbon dots prepared from Epipremnum Aureum leaves extract for biological imaging. Acta Physico-Chimica Sinica, 2026, 42(2): 100134-0. doi: 10.1016/j.actphy.2025.100134
18. [18]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
19. [19]
  Xinwan Zhao , Yue Cao , Minjun Lei , Zhiliang Jin , Tsubaki Noritatsu . Constructing S-scheme heterojunctions by integrating covalent organic frameworks with transition metal sulfides for efficient noble-metal-free photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(12): 100152-0. doi: 10.1016/j.actphy.2025.100152
20. [20]
  Jingping Li , Suding Yan , Jiaxi Wu , Qiang Cheng , Kai Wang . Improving hydrogen peroxide photosynthesis over inorganic/organic S-scheme photocatalyst with LiFePO₄. Acta Physico-Chimica Sinica, 2025, 41(9): 100104-0. doi: 10.1016/j.actphy.2025.100104

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(904)
HTML views(119)

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

A Novel Isolongifolanylindazole Derivatives Colorimetric Probe for Naked-eye Detection of H2S in Water Environment

Metrics

通讯作者: 陈斌, bchen63@163.com

A Novel Isolongifolanylindazole Derivatives Colorimetric Probe for Naked-eye Detection of H₂S in Water Environment