Citation: Yuxin Wang, Zhengxuan Song, Yutao Liu, Yang Chen, Jinping Li, Libo Li, Jia Yao. Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity[J]. Chinese Chemical Letters, ;2024, 35(6): 108779. doi: 10.1016/j.cclet.2023.108779 shu

Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity

Yuxin Wang ^a ,
Zhengxuan Song ^a ,
Yutao Liu ^a ,
Yang Chen ^a ,
Jinping Li ^a ,
Libo Li ^{a, *,} ,
Jia Yao ^{b, *,}

a.
College of Chemical Engineering and Technology, Shanxi Key Laboratory of Gas Energy Efficient and Clean Utilization, Taiyuan University of Technology, Taiyuan 030024, China
b.
Department of Gastroenterology, Shanxi Bethune Hospital, Shanxi Academy of Medical Sciences, Tongji Shanxi Hospital, Third Hospital of Shanxi Medical University, Taiyuan 030024, China

lilibo@tyut.edu.cn

yaojia2006@163.com

Received Date: 29 March 2023
Revised Date: 6 June 2023
Accepted Date: 5 July 2023
Available Online: 6 July 2023

Figures(6)

Exhaled ammonia (NH₃) can be used as a crucial biomarker of kidney and liver diseases. However, the high humidity in the detection conditions remains a challenge for accurate detection by gas sensors. Herein, a copper-based metal-organic framework (CH₃-Cu-BTC) with methyl (CH₃-) functionalization of trimesic acid was synthesized for NH₃ colorimetric sensing. The CH₃-Cu-BTC exhibited a strong response for 5 ppm NH₃ with high selectivity under high relative humidity (75% RH). Density functional theory (DFT) simulations indicated that the NH₃ molecules interacted more strongly with CH₃-Cu-BTC than H₂O molecules did, and the corresponding color switching was attributed to the lone-pair electron in NH₃ changing the coordination environment of Cu²⁺ ions, leading to an obviously visible color switching response from ruby green to blue. Based on the tailor-made pore chemistry, the precise detection of trace amounts of NH₃ in exhaled air was realized through functionalized MOF materials. The strategy used in this study not only offers a new pathway for the rapid detection of low concentration NH₃ under humid conditions, but also shows a method for early respiration diagnosis of kidney and liver diseases.
- Metal-organic framework,
- Ammonia sensing,
- Naked-eye color switching,
- High humidity,
- Respiration diagnosis
1. [1]
  L. Liu, T. Fei, X. Guan, et al., Sens. Actuators B Chem. 320 (2020) 128318. doi: 10.1016/j.snb.2020.128318
2. [2]
  P.Le Maout, J.L. Wojkiewicz, N. Redon, et al., Sens. Actuators B Chem. 274 (2018) 616–626. doi: 10.1016/j.snb.2018.07.178
3. [3]
  Y. Su, G. Chen, C. Chen, et al., Adv. Mater. 33 (2021) 2101262. doi: 10.1002/adma.202101262
4. [4]
  P. Španěl, S. Davies, D. Smith, et al., Rapid Commun. Mass Spectrom. 12 (1998) 763–766. doi: 10.1002/(SICI)1097-0231(19980630)12:12<763::AID-RCM229>3.0.CO;2-S
5. [5]
  C. Turner, P. Španěl, D. Smith, Physiol. Meas. 27 (2006) 321–337. doi: 10.1088/0967-3334/27/4/001
6. [6]
  T. Hibbard, A.J. Killard, Crit. Rev. Anal. Chem. 41 (2011) 21–35. doi: 10.1080/10408347.2011.521729
7. [7]
  S. Davies, P. Spanel, D. Smith, Kidney Int. 52 (1997) 223–228. doi: 10.1038/ki.1997.324
8. [8]
  Z.H. Endre, J.W. Pickering, M.K. Storer, et al., Physiol. Meas. 32 (2011) 115–130. doi: 10.1088/0967-3334/32/1/008
9. [9]
  S.T. Krishnan, J.P. Devadhasan, S. Kim, Anal. Bioanal. Chem. 409 (2017) 21–31. doi: 10.1007/s00216-016-9903-3
10. [10]
  H. Zhao, L. Liu, X. Lin, et al., ACS Sens. 5 (2020) 346–352. doi: 10.1021/acssensors.9b01763
11. [11]
  Y. Liu, B. Sang, H. Wang, et al., Chin. Chem. Lett. 31 (2020) 2109–2114. doi: 10.1016/j.cclet.2019.12.030
12. [12]
  H. Yuan, N. Li, W. Fan, et al., Adv. Sci. 9 (2022) 2104374. doi: 10.1002/advs.202104374
13. [13]
  Y. Li, N. Luo, W. Zhang, et al., J. Mater. Chem. C 8 (2020) 12418–12426. doi: 10.1039/d0tc01650k
14. [14]
  Y. Lin, W. Li, Y. Wen, et al., Angew. Chem. Int. Ed. 60 (2021) 25758–25761. doi: 10.1002/anie.202111519
15. [15]
  W. Zhang, J. Zhao, C. Cai, et al., Adv. Sci. 9 (2022) 2203428. doi: 10.1002/advs.202203428
16. [16]
  A.W. Jones, Clin. Sci. 63 (1982) 441–445. doi: 10.1042/cs0630441
17. [17]
  A.H. Assen, O. Yassine, O. Shekhah, et al., ACS Sens. 2 (2017) 1294–1301. doi: 10.1021/acssensors.7b00304
18. [18]
  Z. Qiu, Y. Xue, J. Li, et al., Chin. Chem. Lett. 32 (2021) 2807–2811. doi: 10.1016/j.cclet.2021.02.029
19. [19]
  H. Furukawa, N. Ko, Y.B. Go, et al., Science. 329 (2010) 424–428. doi: 10.1126/science.1192160
20. [20]
  J. Li, J. Kuppler, H. Zhou, Chem. Soc. Rev. 38 (2009) 1477–1504. doi: 10.1039/b802426j
21. [21]
  E.D. Bloch, W.L. Queen, R. Krishna, et al., Science 335 (2012) 1606–1610. doi: 10.1126/science.1217544
22. [22]
  L. Li, R. Lin, R. Krishna, et al., Science 362 (2018) 443–446. doi: 10.1126/science.aat0586
23. [23]
  L. Dong, L. Zhang, J. Liu, et al., Angew. Chem. Int. Ed. 59 (2020) 2659–2663. doi: 10.1002/anie.201913284
24. [24]
  P. Liao, N. Huang, W. Zhang, et al., Science 356 (2017) 1193–1196. doi: 10.1126/science.aam7232
25. [25]
  A. Cadiau, K. Adil, P.M. Bhatt, et al., Science 353 (2016) 137–140. doi: 10.1126/science.aaf6323
26. [26]
  N. Li, R. Feng, J. Zhu, et al., Coord. Chem. Rev. 375 (2018) 558–586. doi: 10.1016/j.ccr.2018.05.016
27. [27]
  X. Cui, K. Chen, H. Xing, et al., Science 353 (2016) 141–144. doi: 10.1126/science.aaf2458
28. [28]
  Y. Feng, Y. Wang, Y. Ying, Coordin. Chem. Rev. 446 (2021) 214102. doi: 10.1016/j.ccr.2021.214102
29. [29]
  H. Li, S. Zhao, S. Zang, et al., Chem. Soc. Rev. 49 (2020) 6364–6401. doi: 10.1039/c9cs00778d
30. [30]
  Q. Sui, P. Li, N. Yang, et al., ACS Appl. Mater. Interfaces 10 (2018) 11056–11062. doi: 10.1021/acsami.8b01314
31. [31]
  B. Tan, C. Chen, L. Cai, et al., Inorg. Chem. 54 (2015) 3456–3461. doi: 10.1021/acs.inorgchem.5b00023
32. [32]
  A. Gładysiak, T.N. Nguyen, J.A.R. Navarro, et al., Chem. Eur. J. 23 (2017) 13602–13606. doi: 10.1002/chem.201703510
33. [33]
  S. Sotirov, S. Demirci, M. Marudova, et al., IEEE Sens. J. 22 (2022) 3903–3910. doi: 10.1109/jsen.2022.3145046
34. [34]
  J. Zhang, J. Ouyang, Y. Ye, et al., ACS Appl. Mater. Interfaces 10 (2018) 27465–27471. doi: 10.1021/acsami.8b07770
35. [35]
  P. Goel, S. Singh, H. Kaur, et al., Sens. Actuators B Chem. 329 (2021) 129157. doi: 10.1016/j.snb.2020.129157
36. [36]
  S. Feng, Q. Tang, Z. Xu, et al., Food Hydrocoll. 135 (2023) 108193. doi: 10.1016/j.foodhyd.2022.108193
37. [37]
  S. Xiang, W. Zhou, J.M. Gallegos, et al., J. Am. Chem. Soc. 131 (2009) 12415–12419. doi: 10.1021/ja904782h
38. [38]
  G.W. Peterson, D.K. Britt, D.T. Sun, et al., Ind. Eng. Chem. Res. 54 (2015) 3626–3633. doi: 10.1021/acs.iecr.5b00458
39. [39]
  P.Z. Moghadam, D. Fairen-Jimenez, R.Q. Snurr, J. Mater. Chem. A 4 (2016) 529–536. doi: 10.1039/C5TA06472D
40. [40]
  Y. Khabzina, D. Farrusseng, Microporous Mesoporous Mater. 265 (2018) 143–148. doi: 10.1016/j.micromeso.2018.02.011
41. [41]
  Y. Cai, A.R. Kulkarni, Y. Huang, et al., Cryst. Growth Des. 14 (2014) 6122–6128. doi: 10.1021/cg501285q
42. [42]
  S. Rong, P. Su, S. Chen, et al., Chin. Chem. Lett. 33 (2022) 2134–2138. doi: 10.1016/j.cclet.2021.09.012
43. [43]
  Y. Cai, Y. Zhang, Y. Huang, et al., Cryst. Growth Des. 12 (2012) 3709–3713. doi: 10.1021/cg300518k
44. [44]
  B. Seoane, C. Téllez, J. Coronas, et al., Sep. Purif. Technol. 111 (2013) 72–81. doi: 10.1016/j.seppur.2013.03.034
45. [45]
  L. Li, Y. Wang, J. Yang, et al., Chempluschem 81 (2016) 222–228. doi: 10.1002/cplu.201500445
46. [46]
  Y. Cheng, Q. Feng, M. Yin, et al., Tetrahedron Lett. 57 (2016) 3814–3818. doi: 10.1016/j.tetlet.2016.07.013
47. [47]
  Y. Li, S. Li, Y. Jiang, et al., Chem. Commun. 54 (2018) 9789–9792. doi: 10.1039/c8cc05459b
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