Synthesis of Symmetrical Acetophenone Azine Derivatives as Colorimetric and Fluorescent Cyanide Chemosensors

https://doi.org/10.22146/ijc.64428

Nur Masyittah Irmi(1), Bambang Purwono(2*), Chairil Anwar(3)

(1) Department of Chemistry, Faculty Mathematics and Natural Science, Universitas Gadjah Mada, Sekip Utara, PO BOX BLS 21, Yogyakarta 55281, Indonesia
(2) Department of Chemistry, Faculty Mathematics and Natural Science, Universitas Gadjah Mada, Sekip Utara, PO BOX BLS 21, Yogyakarta 55281, Indonesia
(3) Department of Chemistry, Faculty Mathematics and Natural Science, Universitas Gadjah Mada, Sekip Utara, PO BOX BLS 21, Yogyakarta 55281, Indonesia
(*) Corresponding Author

Abstract


Cyanide is a highly toxic anion and poison to the environment. Therefore, fast, effective, and efficient analysis methods to detect cyanide are needed. Herein, symmetrical chemosensor of 2’-hydroxy acetophenone azine (1) and 2’,4’-dihydroxy acetophenone azine (2) has been synthesized tested as colorimetric and fluorescent cyanide chemosensor. The azines were produced from the condensation of acetophenone derivatives with hydrazine hydrate in ethanol under reflux or ultrasonic irradiation methods. Colorimetric and fluorescent chemosensor tests showed selectivity to acetate and cyanide anions in DMSO. The limit of detection (LOD) for colorimetric measurement of cyanide anion was 9.68×10–4 M for compound (1) and 9.63×10–5 M for compound (2), while the fluorescent method showed 15.90×10–4 M for compound (1) and 8.95×10–5 M for compound (2), respectively. In addition, test paper-strips containing sensor 2 indicated noticeable results for 'naked eye' detection of cyanide in an aqueous medium.

Keywords


acetophenone; azine; colorimetry; fluorescents; cyanide

Full Text:

Full Text PDF


References

[1] Pei, P.X., Hu, J.H., Chen, Y., Sun, Y., and Qi, J., 2017, A novel dual-channel chemosensor for CN using asymmetric double-azine derivatives in aqueous media and its application in bitter almond, Spectrochim. Acta, Part A, 181, 131–136.

[2] Jia, X., Yang, Y., He, Y., Ma, Q., and Liu, Y., 2019, Theoretical study on the sensing mechanism of a fluorescence chemosensor for the cyanide anion, Spectrochim. Acta, Part A, 216, 258–264.

[3] Erdemir, S., and Malkondu, S., 2020, On-site and low-cost detection of cyanide by simple colorimetric and fluorogenic sensors: Smartphone and test strip applications, Talanta, 207, 120278.

[4] Ferreira, N.L, de Cordova, L.M., Schramm, A.D.S., Nicoleti, C.R., and Machado, V.G., 2019, Chromogenic and fluorogenic chemodosimeter derived from Meldrum's acid detects cyanide and sulfide in aqueous medium, J. Mol. Liq., 282, 142–153.

[5] Yu, B., Li, C.Y., Sun, Y.X., Jia, H.R., Guo, J.Q., and Li, J., 2017, A new azine derivative colorimetric and fluorescent dual-channel probe for cyanide detection, Spectrochim. Acta, Part A, 184, 249–254.

[6] Udhayakumari, D., 2018, Chromogenic and fluorogenic chemosensors for lethal cyanide ion. A comprehensive review of the year 2016, Sens. Actuators, B, 259, 1022–1057.

[7] Tracqui, A., Raul, J.S., Géraut, A., Berthelon, L., and Ludes, B., 2002, Determination of blood cyanide by HPLC-MS, J. Anal. Toxicol., 26 (3), 144–148.

[8] Dadfarnia, S., Haji Shabani, A.M., Tamadon, F., and Rezaei, M., 2007, Indirect determination of free cyanide in water and industrial waste water by flow injection-atomic absorption spectrometry, Microchim. Acta, 158 (1), 159–163.

[9] Taheri, A., Noroozifar, M., and Khorasani, M.M., 2009, Investigation of a new electrochemical cyanide sensor based on Ag nanoparticles embedded in a three dimensional solegel, J. Electroanal. Chem., 628 (1-2), 48–54.

[10] Mergu, N., Singh, A.K., and Gupta, V.K., 2015, Highly sensitive and selective colorimetric and off-on fluorescent reversible chemosensors for Al3+ based on the rhodamine fluorophore, Sensors, 15 (4), 9097–9111.

[11] Sun, Y., Hu, J.H., Qi, J., and Li, J.B., 2016, A highly selective colorimetric and "turn-on" fluorimetric chemosensor for detecting CN based on unsymmetrical azine derivatives in aqueous media, Spectrochim. Acta, Part A, 167, 101–105.

[12] Pei, P.X., Hu, J.H., Long, C., and Ni. P.W., 2018, A novel colorimetric and "turn-on" fluorimetric chemosensor for selective recognition of CN ions based on asymmetric azine derivatives in aqueous media, Spectrochim. Acta, Part A, 198, 182–187.

[13] Hu, J.H., Sun, Y., Qi, J., Li, Q., and Wei, T.B., 2017, A new unsymmetrical azine derivative based on coumarin group as dual-modal sensor for CN and fluorescent "OFF-ON" for Zn2+, Spectrochim. Acta, Part A, 175, 125–133.

[14] Hidayah, N., Purwono, B., and Pranowo, H.D., 2020, One step synthesis of symmetrical amino azine derivatives using hydrazine hydrate as a reagent, Key Eng. Mater., 840, 257–264.

[15] Kagatikar, S., Sunil, D., Kekuda, D., Kulkarni, S.D., and Abdul Salam, A.A., 2020, New salicylaldehyde azine esters: Structural, aggregation induced fluorescence, electrochemical and theoretical studies, J. Mol. Liq., 318, 114029.

[16] Lee, B., Lee, K.H., Cho, J., Nam, W., and Hur, N.H., 2011, Synthesis of azines in solid state: Reactivity of solid hydrazine with aldehydes and ketones, Org. Lett., 13 (24), 6386–6389.

[17] Safari, J., and Gandomi-Ravandi, S., 2011, Highly efficient practical procedure for the synthesis of azine derivatives under solvent-free conditions, Synth. Commun., 41 (5), 645–651.

[18] Li, W.J., and Han, H.F., 2016, Crystal structure of (E,E)-2’,4’-dihydroxyacetophenone azine dimethylformamide disolvate, Acta Crystallogr., Sect. E: Crystallogr. Commun., E72, 467–469.

[19] Mohammadi, A., and Yaghoubi, S., 2017, A new dual colorimetric chemosensor based on quinazolinone for CN, AcO and Cu2+ ions, Sens. Actuators, B, 241, 1069–1075.

[20] Nie, H.M., Gong, C.B., Tang, Q., Ma, X.B., and Chow, C.F., 2014, Visual and reversible detection of cyanide ions in protic solvents by a novel colorimetric receptor, Dyes Pigm., 106, 74–80.

[21] Lin, S.L., Kuo, P.Y., and Yang, D.Y., 2007, Design and synthesis of a coumarin-based acidichromic colorant, Molecules, 12 (7), 1316–1324.

[22] Purwono, B., Anwar, C., and Hanapi, A., 2013, Syntheses of azo-imine derivatives from vanillin as an acid base indicator, Indones. J. Chem., 13 (1), 1–6.

[23] Murugesan, K., Jeyasingh, V., Lakshminarayan, S., Selvapalam, N., Dass, G., and Piramuthu, L., 2021, Anion-binding-induced and reduced fluorescence emission (ABIFE & ABRFE): A fluorescent chemo sensor for selective turn-on/off detection of cyanide and fluoride, Spectrochim. Acta, Part A, 245, 118943.



DOI: https://doi.org/10.22146/ijc.64428

Article Metrics

Abstract views : 1520 | views : 1497


Copyright (c) 2021 Indonesian Journal of Chemistry

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

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.