Citation: PAN Mingguang, ZHAO Yongsheng, ZENG Xiaoqin, ZOU Jianxin. Moisture-Responsive Behavior in the Azophenolic Ionic Liquid Solution Accompanied by a Naked-Eye Color Change[J]. Acta Physico-Chimica Sinica, ;2019, 35(6): 624-629. doi: 10.3866/PKU.WHXB201807035 shu

Moisture-Responsive Behavior in the Azophenolic Ionic Liquid Solution Accompanied by a Naked-Eye Color Change

1.
National Engineering Research Center of Light Alloy Net Forming, State Key Laboratory of Metal Matrix Composite, School of Materials Science and Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China
2.
Department of Micro/Nano-electronics, Shanghai Jiao Tong University, Shanghai 200240, P. R. China

Corresponding author: PAN Mingguang, panmingguang@sjtu.edu.cn ZOU Jianxin, zoujx@sjtu.edu.cn
Received Date: 16 July 2018
Revised Date: 23 August 2018
Accepted Date: 23 August 2018
Available Online: 27 June 2018
Fund Project: The project was supported by the China Postdoctoral Science Foundation (2017M621476, 2017M621477) and National Natural Science Foundation of China (51771112)the China Postdoctoral Science Foundation 2017M621476National Natural Science Foundation of China 51771112the China Postdoctoral Science Foundation 2017M621477

Room temperature ionic liquids (ILs) that can exhibit a colorimetric response to moisture in the air are rarely reported in the literature. In this study, an azophenolic IL solution exhibited a spontaneous a colorimetric response, driven by the formation of hydrogen bonding between the [PhN＝NPhO] anion and moisture in the air. This phenomenon was clearly understood using ultraviolet-visible (UV-Vis) absorption spectroscopy, nuclear magnetic resonance (NMR) spectra, experimental data, and theoretical calculations. Specifically, in the UV-Vis absorption spectra, absorption around 455 nm decreased, while the band around 343 nm increased in the IL CHCl₃ solution as time progressed; this was accompanied by a color change from orange to faint yellow. This spontaneous, self-responsive process was further observed using ¹H NMR data. When the IL solution was placed with sufficient time, all the ¹H NMR peaks of the azophenolic anion shifted downfield, but no new signals appeared in the upfield region. The reason for this was easily identified as the stimuli in the air, such as CO₂ and moisture. When pure CO₂ was bubbled through the IL CHCl₃ solution, the solution color changed from its original orange to light orange, but could not change further to faint yellow, which ruled out CO₂ gas as a stimulus. When a small amount of water was gradually added to the IL solution (MeCN solvent), the absorption band around 474 nm decreased, coupled with an increase in the absorption band around 347 nm. This was accompanied by a color change from orange to faint yellow, which was almost identical to the self-responsive process in CHCl₃ and CCl₄. Moreover, two cuvettes of IL CHCl₃ solution were placed under relative humidities of 28% and 100%, respectively; the IL CHCl₃ solution required a much longer time to exhibit a complete color change from orange to faint yellow under a lower relative humidity, demonstrating that moisture is the most likely stimulus triggering the self-responsive color change of the IL solution. As revealed by the Gaussian 09 program at the B3LYP/6-31++G(p, d) level, the distance between the oxygen atom on the azophenolic anion and the hydrogen atom on the H₂O molecule was 0.174 nm, and the corresponding angle was 171.12°. Furthermore, the atomic dipole moment corrected Hirshfeld (ADCH) charge of the oxygen atom on the azophenolic anion was −0.52, and it increased to −0.62 after the azophenolic anion interacted with the H₂O. Reduced density gradient analysis revealed that the spike corresponding to O∙∙∙H―O for the IL-H₂O complex was located at around −0.04 a.u.. All the above data indicate that the presence of hydrogen bonding rendered the IL solution responsive to the moisture stimulus, and this response was accompanied by a color change that was visible to the naked eye. To the best of our knowledge, this is the first demonstration of a colorimetric change in an IL solution in response to moisture. We hope this work can help us to gain insight into some seemingly abnormal phenomena that occur during the research process.
- Stimuli-responsive,
- Moisture,
- Colorimetric change,
- Hydrogen bonding,
- Ionic liquid solution
1. [1]
  Wojtecki, R. J.; Meador, M. A.; Rowan, S. J. Nat. Mater. 2011, 10, 14. doi: 10.1038/nmat2891 doi: 10.1038/nmat2891
2. [2]
  Stuart, M. A. C.; Huck, W. T. S.; Genzer, J.; Müller, M.; Ober, C.; Stamm, M.; Sukhorukov, G. B.; Szleifer, I.; Tsukruk, V. V.; Urban, M.; et al. Nat. Mater. 2010, 9, 101. doi: 10.1038/nmat2614 doi: 10.1038/nmat2614
3. [3]
  Lendlein, A.; Jiang, H.; Jünger, O.; Langer, R. Nature 2005, 434, 879. doi: 10.1038/ nature03496 doi: 10.1038/nature03496
4. [4]
  Ma, M.; Guo, L.; Anderson, D. G.; Langer, R. Science 2013, 339, 186. doi: 10.1126/science.1230262 doi: 10.1126/science.1230262
5. [5]
  Kim, J.; Hanna, J. A.; Byun, M.; Santangelo, C. D.; Hayward, R. C. Science 2012, 335, 1201. doi: 10.1126/science.1215309 doi: 10.1126/science.1215309
6. [6]
  Yan, X.; Wang, F.; Zeng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042. doi: 10.1039/C2CS35091B doi: 10.1039/C2CS35091B
7. [7]
  Folmer, B. J. B.; Sijbesma, R. P.; Versteegen, R. M.; van der Rijt, J. A. J.; Meijer, E. W. Adv. Mater. 2000, 12, 874. doi: 10.1002/1521- 4095(200006)12:12 < 874::AID-ADMA874>3.0.CO; 2-C doi: 10.1002/1521-4095(200006)12:12<874::AID-ADMA874>3.0.CO;2-C
8. [8]
  Liao, X.; Chen, G.; Liu, X.; Chen, W.; Chen, F.; Jiang, M. Angew. Chem. Int. Ed. 2010, 49, 4409. doi: 10.1002/ange.201000141 doi: 10.1002/ange.201000141
9. [9]
  Xie, T. Nature 2010, 464, 267. doi: 10.1038/nature08863 doi: 10.1038/nature08863
10. [10]
  Aida, T.; Meiger, E. W.; Stupp, S. I. Science 2012, 335, 813. doi: 10.1126/science.1205962 doi: 10.1126/science.1205962
11. [11]
  Jeon, Y. J.; Bharadwaj, P. K.; Choi, S.; Lee, J. W.; Kim, K. Angew. Chem. Int. Ed. 2002, 41, 4474. doi: 10.1002/1521-3773(20021202) 41:23 < 4474::AID-ANIE4474>3.0.CO; 2-S doi: 10.1002/1521-3773(20021202)41:23<4474::AID-ANIE4474>3.0.CO;2-S
12. [12]
  Thibault, R. J.; Hotchkiss, P. J.; Gray, M.; Rotello, V. M. J. Am. Chem. Soc. 2003, 125, 11249. doi: 10.1021/ja034868b doi: 10.1021/ja034868b
13. [13]
  Wilson, A. J. Soft Matter 2007, 3, 409. doi: 10.1039/B612566B doi: 10.1039/B612566B
14. [14]
  Zhang, X.; Wang, C. Chem. Soc. Rev. 2011, 40, 94. doi: 10.1039/B919678C doi: 10.1039/B919678C
15. [15]
  Tao, W.; Liu, Y.; Jiang, B.; Yu, S.; Huang, W.; Zhou, Y.; Yan, D. J. Am. Chem. Soc. 2012, 134, 762. doi: 10.1021/ja207924w doi: 10.1021/ja207924w
16. [16]
  Neal, J. A.; Mozhdehi, D.; Guan, Z. J. Am. Chem. Soc. 2015, 137, 4846. doi: 10.1021/jacs.5b01601 doi: 10.1021/jacs.5b01601
17. [17]
  Xu, X.; Song, C.; Miller, B. G.; Scaoni, A. W. Ind. Eng. Chem. Res. 2005, 44, 8113. doi: 10.1021/ie050382n doi: 10.1021/ie050382n
18. [18]
  McDanel, W. M.; Cowan, M. G.; Chisholm, N. O.; Gin, D. L.; Noble, R. D. J. Membr. Sci. 2015, 492, 303. doi: 10.1016/j.memsci.2015.05.034 doi: 10.1016/j.memsci.2015.05.034
19. [19]
  Zeng, R.; Zhang, J.; Huang, W.; Dietzel, W.; Kainer, K. U.; Blawert, C.; Ke, W. Trans. Nonferrous Met. Soc. 2006, 16, s763. doi: 10.1016/S1003-6326(06)60297-5 doi: 10.1016/S1003-6326(06)60297-5
20. [20]
  Li, C.; Chen, L. Chem. Soc. Rev. 2006, 35, 68. doi: 10.1039/B507207G doi: 10.1039/B507207G
21. [21]
  Wu, W. Z.; Han, B. X.; Gao, H. X.; Liu, Z. M.; Jiang, T.; Huang, J. Angew. Chem. Int. Ed. 2004, 43, 2415. doi: 10.1002/ange.200353437 doi: 10.1002/ange.200353437
22. [22]
  Huang, J. F.; Luo, H. M.; Liang, C. D.; Sun, I. W.; Baker, G. A.; Dai, S. J. Am. Chem. Soc. 2005, 127, 12784. doi: 10.1021/ja053965x doi: 10.1021/ja053965x
23. [23]
  Armond, M.; Endres, F.; MacFarlane, D. R.; Ohno, H.; Scrosati, B. Nat. Mater. 2009, 8, 621. doi: 10.1038/nmat2448 doi: 10.1038/nmat2448
24. [24]
  Cui, G.; Wang, J.; Zhang, S. Chem. Soc. Rev. 2016, 45, 4307. doi: 10.1039/C5CS00462D doi: 10.1039/C5CS00462D
25. [25]
  Zeng, S.; Zhang, X.; Bai, L.; Zhang, X.; Wang, H.; Wang, J.; Bao, D.; Li, M.; Liu, X.; Zhang, S. Chem. Rev. 2017, 117, 9625. doi: 10.1021/acs.chemrev.7b00072 doi: 10.1021/acs.chemrev.7b00072
26. [26]
  Han, B. Acta Phys. -Chim. Sin. 2018, 34, 451. doi: 10.3866/PKU.WHXB201710122
27. [27]
  Zhao, Y.; Pan, M.; Kang, X.; Tu, W.; Gao, H.; Zhang, X. Chem. Eng. Sci. 2018, 189, 43. doi: 10.1016/j.ces.2018.05.044 doi: 10.1016/j.ces.2018.05.044
28. [28]
  Pan, M.; Zhao, Y.; Zeng, X.; Zou, J. Energy Fuels 2018, 32, 6130. doi: 10.1021/acs.energyfuels.8b00879 doi: 10.1021/acs.energyfuels.8b00879
29. [29]
  Jessop, P. G.; Heldebrant, D. J.; Li, X.; Eckert, C. A.; Liotta, C. L. Nature 2005, 436, 1102. doi: 10.1038/4361102a doi: 10.1038/4361102a
30. [30]
  Liu, Y.; Tang, T.; Barashkov, N. N.; Irgibaeva, I. S.; Lam, J. W. Y.; Hu, R.; Birimzhanova, D.; Yu, Y.; Tang, B. Z. J. Am. Chem. Soc. 2010, 132, 13951. doi: 10.1021/ja103947j doi: 10.1021/ja103947j
31. [31]
  Che, S.; Dao, R.; Zhang, W.; Lv, X.; Li, H.; Wang, C. Chem. Commun. 2017, 53, 3862. doi: 10.1039/C7CC00676D doi: 10.1039/C7CC00676D
32. [32]
  Wang, C.; Luo, H.; Jiang, D. E.; Li, H.; Dai, S. Angew. Chem. Int. Ed. 2010, 49, 5978. doi: 10.1002/ange.201002641 doi: 10.1002/ange.201002641
33. [33]
  Jin, Z.; Xie, D. X.; Zhang, X. B.; Gong, Y. J.; Tan, W. Anal. Chem. 2012, 84, 4253. doi: 10.1021/ac300676v doi: 10.1021/ac300676v
34. [34]
  Must, I.; Vonder, V.; Kassik, F.; Põldsalu, I.; Johanson, U.; Punning, A.; Aabloo, A. Sensor Actuat. B-Chem. 2014, 202, 114. doi: 10.1016/j.snb.2014.05.074 doi: 10.1016/j.snb.2014.05.074
35. [35]
  Sullivan-González, F.; Scovazzo, P.; Amos, R.; Bae, S.-K. Membr. Sci. 2017, 533, 190. doi: 10.1016/j.memsci.2017.03.026 doi: 10.1016/j.memsci.2017.03.026
36. [36]
  Pan, M.; Cao, N.; Lin, W.; Luo, X.; Chen, K.; Che, S.; Li, H.; Wang, C. ChemSusChem 2016, 9, 2351. doi: 10.1002/cssc.201600402 doi: 10.1002/cssc.201600402
37. [37]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09, Revision C.01; Wallingford, CT: Gaussian Inc., 2010.
38. [38]
  Bortolus, P.; Monti, S. J. Phys. Chem. 1979, 83, 648. doi: 10.1021/j100469a002 doi: 10.1021/j100469a002
39. [39]
  Johnson, E. R.; Keinan, S.; Mori-Sanche, P.; Contretras-Garicia, J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498. doi: 10.1021/ja100936w doi: 10.1021/ja100936w
40. [40]
  Wang, C.; Luo, X.; Luo, H.; Jiang, D. E.; Li, H.; Dai, S. Angew. Chem. Int. Ed. 2011, 50, 4918. doi: 10.1002/ange.201008151 doi: 10.1002/ange.201008151
41. [41]
  Cao, L.; Zhu, P.; Zhao, Y.; Zhao, J. J. Hazard Mater. 2018, 352, 17. doi: 10.1016/j.jhazmat.2018.03.025 doi: 10.1016/j.jhazmat.2018.03.025
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