Styrene and Azo-Styrene Based Colorimetric Sensors for Highly Selective Detection of Cyanide

https://doi.org/10.22146/ijc.24887

Agustina Eka Prestiani(1*), Bambang Purwono(2),

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(*) Corresponding Author

Abstract


A novel styrene (1) and azo-styrene (2) based chemosensor from vanillin has been successfully synthesized. Sensor 1 was obtained by one step Knoevenagel condensation of Ultrasound method and sensor 2 by coupling diazo and Knoevenagel condensation reaction. Both of sensors showed high sensitivity and selectivity to detect CN- in aqueous media, even the presence of other anions, such as F-, Cl-, Br-, I-, CO32-, SO42-, H2PO4-, and AcO-. Colorimetric sensing of sensor 1 is inclined to be deprotonating of sensor binding site in the presence of cyanide and consequently improve the selectivity and sensitivity in sensing cyanide which displayed color change of sensor from yellowness to red-purple and then purple in 1 min. Sensor 2 exhibited chemodosimeter phenomenon which is caused by the nucleophilic addition of cyanide with a colour change from green to greenish-blue. The results enable to do an anion detection by a naked eye.

Keywords


colorimetric chemosensor; styrene; azo-styrene; cyanide

Full Text:

Full Text PDF


References

[1] Lin, W.C., Hu, J.W., and Chen, K.Y., 2015, A ratiometric chemodosimeter for highly selective naked-eye and fluorogenic detection of cyanide, Anal. Chim. Acta, 893, 91–100.

[2] Kulig, K.W., and Ballantyne, B., 1991, Cyanide Toxicity, US Department of Health & Human Service, Public Health Service, Agency for toxic Substance and Dease Registry.

[3] Na, S.Y., and Kim, H.J., 2015, Azo dye-based colorimetric chemodosimeter for the rapid and selective sensing of cyanide in aqueous solvent, Tetrahedron Lett., 56 (3), 493–495.

[4] Wang, F., Wang, L., Chen, X., and Yoon, J., 2010, Recent progress in the development of fluorometric and colorimetric chemosensors for detection of cyanide ions, Chem. Soc. Rev., 43 (13), 127–123.

[5] Yang, Z., Zhang, K., Gong, F., Li, S., Chen, J., Ma, J.S., Sobenina, L.N., Mikhaleva, A.I., Trofimov, B.A., and Yang, G., 2011, A highly selective fluorescent sensor for fluoride anion based on pyrazole derivative: Naked eye “no–yes” detection, J. Photochem. Photobiol., A, 217, 29–34.

[6] Suganya, S., and Velmathi, S., 2015, Fluorogenic and chromogenic heterocyclic thiourea: Selective recognition of cyanide ion via nucleophilic addition reaction and real sample analysis, Sens. Actuators, B, 221, 1104–1113.

[7] Dalapati, S., Jana, S., and Guchait, N., 2014, Anion recognition by simple chromogenic and chromo-fluorogenic salicylidene Schiff base or reduced-Schiff base receptors, Spectrochim. Acta, Part A, 129, 499–508.

[8] Shao, J., 2010, A novel colorimetric and fluorescence anion sensor with a urea group as binding site and a coumarin group as signal unit, Dyes Pigm., 87 (3), 272–276.

[9] Velmathi, S., Reena, V., Sungaya, S., and Anandan, S., 2012, Pyrrole based Schiff bases as colorimetric and fluorescent chemosensors for fluoride and hydroxide anions, J. Fluoresc., 22 (1), 155–162.

[10] Tisseh, Z.N., Dabiri, M., Nobahar, M., Khavasi H.R., and Bazgir, A., 2011, Catalyst-free, aqueous and highly diastereoselective synthesis of new 5-substituted 1H-tetrazoles via a multi-component domino Knoevenagel condensation 1,3-dipolar cycloaddition reaction, Tetrahedron, 68 (6), 1769–1773.

[11] Nigam, S., and Rutan, S., 2001, Principles and application of solvatochromism, Appl. Spectrosc., 55 (11), 362–370.

[12] Hadjmohammadi, M.R., Chaichi, M.J., and Yousefpour, M., 2008, Solvatochromism effect of different solvents on UV-Vis spectra of flouresceine and its derivatives, Iran. J. Chem. Chem. Eng., 22 (4), 9–14.

[13] Sun, Y., Liu, Y., and Guo, W., 2009, Fluorescent and chromogenic probes bearing salicylaldehyde hydrazone functionality for cyanide detection in aqueous solution, Sens. Actuators, B, 143 (1), 171–176.

[14] Li, J.Y., Zhou, X.Q., Zhou, Y., Fang, Y., and Yao, C., 2012, A highly specific tetrazole-based chemosensor for fluoride ion: A new sensing functional group based on intramolecular proton transfer, Spectrochim. Acta, Part A, 102, 66–70.

[15] Park, S., Hong, K.H., Hong, J.I., and Kim, H.J., 2012, Azo dye-based latent colorimetric chemodosimeter for the selective detection of cyanides in aqueous buffer, Sens. Actuators, B, 174, 140–144.

[16] Pati, P.B., 2016, Organic chemodosimeter for cyanide: A nucleophilic approach, Sens. Actuators, B, 222, 374–390.

[17] Jayasudha, P., Manivannan, R., and Elango, K.P., 2015, Simple colorimetric chemodosimeters for selective sensing of cyanide ion in aqueous solution via termination of ICT transition by Michael addition, Sens. Actuators, B, 221, 1441–1448.

[18] Udhayakumari, D., and Velmathi, S., 2016, A highly sensitive salophen based colorimetric anion sensor for fluoride and acetate in aqueous medium, J. Chem. Chem. Sci., 6 (2), 88–97.



DOI: https://doi.org/10.22146/ijc.24887

Article Metrics

Abstract views : 151 | views : 149

Refbacks

  • There are currently no refbacks.


Copyright (c) 2017 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Indexed by:


Creative Commons License
Indonesian Journal of Chemistry is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Statistics=

View The Statistics of Indones. J. Chem.