Synthesis of a new azo Schiff base colorimetric chemosensor for detection of cyanide and acetate anions

Document Type : Original Article

Author

Chemistry Department, Payame Noor University (PNU), Tehran 19395-3697, Iran

Abstract

In this paper, a novel azo Schiff base chemosensor was synthesized via condensation reaction of 4-Aminoantipyrine with 1-(3-Formyl-4-hydroxyphenylazo)-3-nitrobenzene. The imine sensor was studied via spectroscopic methods IR, 1HNMR and UV-Vis. The chromogenic behavior of colorimetric chemosensor toward various anions was investigated by UV–Vis spectroscopic. The chemosensor show abrupt changes towards CN− and OAC−anions in DMF/H2O solution in comparison with other anions. Upon the addition of CN− and OAC− ions to the receptor, the color of the L solution was changed from yellow to purple that was detectable with naked-eye and without any optical instrument. No color changes towards other anions were observed. The detection limits of the azo-azomethin sensor for OAC− and CN− anions were 2.6 ×10-5 and 1.4 ×10-6 mol L-1, respectively. Using the association constant value for sensor towards OAC− and CN− anions was calculated to be 4.2 ×103 and 3.07 ×104 M-1.

Keywords

Main Subjects


This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

[1] Wu, D., Sedgwick, A.C., Gunnlaugsson, T., Akkaya, E.U., Yoon, J., James, T.D. (2017). Fluorescent chemosensors: the past, present and future. Chem. Soc. Rev., 46 ,7105-7123.
[2] Gale, P.A., Howe E.N.W., Wu, X. (2016). Anion Receptor Chemistry. Chem., 1, 351-422.
[3] Manna, A. K., Mondal, J., Chandra, R., Rout, K., Patra, G. K. (2018). A fluorescent colorimetric azo dye based chemosensor for detection of S2− in perfect aqueous solution and its application in real sample analysis and building a molecular logic gate. Anal. Methods, 10, 2317-2326.
[4] Kim, H.N., Ren, W.X., Kim, J.S., Yoon, J. (2012). Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chem. Soc. Rev., 41, 3210-3244.
[5] Saleem, M., Rafiq, M., Hanif, M. (2017). Organic Material Based Fluorescent Sensor for Hg2+: a Brief Review on Recent Development. J. Fluoresc., 27, 31-58.
[6] Stetter, J. R., Penrose, W. R., Yao. S. (2003). Sensors, Chemical Sensors, Electrochemical Sensors, And ECS, J. Electrochem. Soc., 150, 11-16.
[7] Sivaraman, G., Iniya, M., Anand, T., Kotla, N.G., Sunnapu, O., Singaravadivel, S., Gulyani, A., Chellappa, D. (2018). Chemically diverse small molecule fluorescent chemosensors for copper ion. Coord. Chem. Rev., 357, 50-104.
[8] Cao, D., Liu, Z., Verwilst, P., Koo, S., Jangjili, P., Kim, J.S., Lin, W. (2019). Coumarin-Based Small-Molecule Fluorescent Chemosensors. Chem. Rev., 119, 10403-10519.
[9] Kim, H.N., Lee, M.H., Kim, H.J., Kim, J.S., Yoon, J. (2008). A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. Chem. Soc. Rev., 37, 1465-1472.
[10] Divsar, F. (2020). Design of an optical sensor based on gold nanoparticles for detecting trace amounts of heavy metals in water samples. J. Of Applied Chemistry, 15(54), 217-226. (in persian)
[11] Rezaei, V., Ghayed-Rahmati, S. (2021). Design a optical sensor based on incorporation of ninhydrin in sol-gel matrix for determination of cyanide. J. Of Applied Chemistry, 16(61), 101-112. (in persian)
[12] Azadbakht R., Khanabadi, J. (2013). A new fluorescent nano-chemosensor using a N2O2 type macrocyclic ligand. J. Of Applied Chemistry, 8(27), 35. (in persian)
[13] Kaur, B., Kaur, N., Kumar, S. (2018). Colorimetric metal ion sensors – A comprehensive review of the years 2011–2016. Coord. Chem. Rev., 358, 13-69.
[14] Jiang, C., He, Y., Liu, Y. (2020). Recent advances in sensors for electrochemical analysis of nitrate in food and environmental matrices. Analyst, 145, 5400-5413.
[16] Sharma, D., Kumar, S.A., Sahoo, S.K. (2014). Vitamin B6 cofactor derived chemosensor for the selective colorimetric detection of acetate anions. Tetrahedron Lett., 55, 927-930.
[17] Devaraj, S., Saravanakumar, D., Kandaswamy, M. (2009). Dual responsive chemosensors for anion and cation: Synthesis and studies of selective chemosensor for F and Cu(II) ions. Sens. Actuators B: Chem. 136(1), 13-19.
[18] Hammud, H.H., Ghannoum, A., Masoud, M.S. (2006). Spectral regression and correlation coefficients of some benzaldimines and salicylaldimines in different solvents. Spectrochim. Acta Part A, 63(2), 255-265.