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 . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
15. [15]
  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
16. [16]
  Yujia LI , Tianyu WANG , Fuxue WANG , Chongchen WANG . Direct Z-scheme MIL-100(Fe)/BiOBr heterojunctions: Construction and photo-Fenton degradation for sulfamethoxazole. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 481-495. doi: 10.11862/CJIC.20230314
17. [17]
  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
18. [18]
  Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155
19. [19]
  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
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(8)
Abstract views(655)
HTML views(75)

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