International Journal of New Chemistry
ISC, DOAJ, CAS, Google Scholar......

Host-Guest Study of Arylazo Salicylaldehydes-Anions: Colorimetric Chemosensor for Fluoride and Acetate Ions

Document Type : Research Paper

Authors

Afsaneh Zonouzi 1
Forouzan Zonouzi 2
Alireza Rahmani 3
Hamid Dezhampanah 4
Bahram Ghalami-Choobar 4

1 University of Tehran

2 Department of Chemistry, University campus 2, University of Guilan, Rasht, Iran

3 Department of Chemistry, University of Tehran, Tehran, Iran

4 Department of Chemistry, Faculty of Science, University of Guilan, 19141, Rasht, Iran

https://doi.org/10.22034/ijnc.2024.2033930.1402
Abstract
Colorimetric anion sensing of 5-aryl azo salicylaldehydes is described via the host-guest (HG) approach. Various anions were tested and the solutions were monitored by UV-Vis spectroscopy. The changes in the color of the azo dye solutions 1 and 2 were measured upon exposure to different anions of TBA salts in DMSO as solvent. These changes in color in the case of fluoride and acetate anions were sensible to the naked eye. Spectroscopic data were used to calculate the association constants (Ka ≈ 105-106) via a non-linear curve fitting approach. Appropriate models for each dye-anion complex (HG) system were assigned based on fitting quality and chemical considerations. The dye: F- system followed the HG model while dye: OAc- seems to follow H2G model. Observed results persisted for at least one hour and no changes were detectable for the samples even by visual inspection or UV-Vis spectroscopy. The detection limit ranges were calculated to be 95-100 µM for F- and 50-60 µM for OAc-.

Keywords

Azo dyes
Anion, UV-Vis Spectroscopy
Subjects
[1] P. D. Beer, P. A. Gale, Angew. Chem. Int. Ed. Engl., 40, 486 (2001). DOI: https://doi.org/10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P
[2] R. Wang, Y. Ma, J. Zhao, A. Zhang, S. Yang, H. Shen, G. Li, Z. Shi, Sens. Actuators B Chem. (2018). DOI: https://doi.org/10.1016/j.snb.2017.12.171
[3] Y. Zhou, J. F. Zhang, J. Yoon, Chem. Rev., 114, 5511 (2014). DOI: https://doi.org/10.1021/cr400352m
[4] E. J. Cho, B. J. Ryu, Y. J. Lee, K. C. Nam, Org. Lett., 7, 2607 (2005). DOI: https://doi.org/10.1021/ol0507470   
[5] F. P. Kuhajda, E. S. Pizer, J. N. Li, N. S. Mani, G. L. Frehywot, C.A. Townsend, Proc. Natl. Acad.  Sci., 97, 3450 (2000). DOI: https://doi.org/10.1073/pnas.97.7.3450
[6] S. Ayoob, A. K. Gupta, Crit. Rev. Environ. Sci. Technol., 36, 433 (2006). DOI: https://doi.org/10.1080/10643380600678112
[7] J. Shao, Dyes Pigm. 87 (2010) 272 DOI: https://doi.org/10.1016/j.dyepig.2010.04.007
[8] Y. Shiraishi, H. Maehara, T. Hirai, Org. Biomol. Chem., 7, 2072 (2009). DOI: https://doi.org/10.1039/B821466B
[9] J. Shao, X. Yu, X. Xu, H. Lin, Z. Cai, H. Lin, Talanta, 79, 547 (2009). DOI: https://doi.org/10.1016/j.talanta.2009.02.023
[10] R. Martinez-Manez, F. Sancenón, Chem. Rev., 103, 4419 (2003). DOI: https://doi.org/10.1021/cr010421e
[11] V. M. Gil, N. C. Oliveira, J. Chem. Educ., 67, 473 (1990). DOI: https://doi.org/10.1021/ed067p473  
[12] P. Thordarson, Chem. Soc. Rev., 40, 1305 (2011). DOI: https://doi.org/10.1039/C0CS00062K
[13] D. M. Marmion, Handbook of US colorants: foods, drugs, cosmetics, and medical devices, John Wiley & Sons, 1991. ISBN: 978-0-471-50074-2
[14] D. Greenwood, US Patent, 4,777, 248A, 1988.
[15] Y. J. Liu, Y.B. Zheng, J. Shi, H. Huang, T. R. Walker, T. J. Huang, Opt. Lett., 34, 2351 (2009). DOI: https://doi.org/10.1364/OL.34.002351
[16] V. P. Pham, T. Galstyan, A. Granger, R. A. Lessard, Jpn. J. Appl. Phys., 36, 429 (1997).  DOI: https://doi.org/10.1143/JJAP.36.429
[17] D.-Y. Chen, J.-Y. Kao, C.-Y. Hsu, C.-H. Tsai, J. Electroanal. Chem., 766, 1 (2016). DOI: https://doi.org/10.1039/C6RA15060H
[18] E. Weglarz-Tomczak, L. Gorecki, Chemik., 66, 1298 (2012).
[19] J. Cognard, T. H. Phan, Mol. Cryst. Liq. Cryst., 68, 207 (1981). DOI: https://doi.org/10.1080/00268948108073565
[20] F. Yang, W. Liu, J. Xie, X. Bai, H. Guo, J Inclusion Phenom Macrocyclic Chem., 76, 311 (2013). DOI: https://doi.org/10.1007/s10847-012-0200-2
[21] F. Yang, Y. Zhang, H. Guo, X. Wei, Sep. Sci. Technol., 48, 1565 (2013). DOI: https://doi.org/10.1080/01496395.2012.745875
[22] M. Israr, F. Faheem, F.T. Minhas, A. Rauf, S. Rauf, M. R. Shah, F. Rahim, K. Shah, M. Bhanger, Am. J. Anal. Chem., 7, 219 (2016). DOI: https://doi.org/10.4236/ajac.2016.72019
[23] E. Mertz, S. C. Zimmerman, J. Am. Chem. Soc., 125, 3424 (2003). DOI: https://doi.org/10.1021/ja0294515
[24] K. S. Moon, N. Singh, G. W. Lee, D. O. Jang, Tetrahedron, 63, 9106 (2007). DOI: https://doi.org/10.1016/j.tet.2007.06.091
[25] S. Suganya, J. S. Park, S. Velmathi, Sens. Actuators B: Chem., 190, 679 (2014). DOI: https://doi.org/10.1016/j.snb.2013.09.010
[26] E. Tummeley, European J. Org. Chem., 251, 174 (1889). DOI: https://doi.org/10.1002/jlac.18892510106
[27] P. Sivaguru, R. Sandhiya, M. Adhiyaman, A. Lalitha, Tetrahedron Lett., 57, 2496 (2016). DOI: https://doi.org/10.1016/j.tetlet.2016.04.097
[28] I. Yavari, A. Zonouzi, R. Hekmat-Shoar, Tetrahedron Lett., 39, 3841 (1998). DOI: https://doi.org/10.1016/S0040-4039(98)00627-3
[29] A. Zonouzi, H. A. Shahrezaee, A. Rahmani, F. Zonouzi, K. Abdi, F. T. Fadaei, K. Shenk, Org. Prep. Proced. Int., 50, 343 (2018). DOI: https://doi.org/10.1080/00304948.2018.1462066
[30] A. Rahmani, H Rahmani, A. Zonouzi, Int J New Chem, 7, 169 (2020). DOI: https://doi.org/10.22034/ijnc.2019.116043.1060
[31] A. Rahmani, H. Rahmani, A. Zonouzi, Chem. Pap., 72, 449 (2018). DOI: https://doi.org/10.1007/s11696-017-0297-2
[32] MS. Asgari, A. Zonouzi, R. Rahimi, M. Rabbani, Orient. J. Chem., 31, 1537 (2015). DOI: https://doi.org/10.13005/ojc/310331
[33] F. Zonouzi, A. Rahmani, H. Dezhampanah, B. Ghalami-Choobar, A. Zonouzi, Chem. Pap., 73, 2409 (2019). DOI:  https://doi.org/10.1007/s11696-019-00790-1
[34] K. A. Connors, Binding constants: the measurement of molecular complex stability, Wiley-Interscience, 1987. DOI: https://doi.org/10.1002/bbpc.19870911223
[35] J. E. D. Davies, J. L. Atwood, J. M. Lehn, Comprehensive supramolecular chemistry, Volume 8, Pergamon, New York, 1996.
[36] J. Szejtli, J. L. Atwood, J. M. Lehn, Comprehensive supramolecular chemistry, Volume 3, Pergamon, New York, 1996.
[37] H.-J. Schneider, A. K. Yatsimirsky, Principles and methods in supramolecular chemistry, J. Wiley, 2000. ISBN: 978-0-471-97253-2
[38] J. E. A. Webb, M. J. Crossley, P. Turner, P. Thordarson, J. Am. Chem. Soc., 129, 7155 (2007). DOI: https://doi.org/10.1021/ja0713781
International Journal of New Chemistry
Volume 12, Issue 1
Winter 2025
Pages 113-124

Home

Reviewers