Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Nevi Faizatu Rokhmah(1), Muhammad Idham Darussalam Mardjan(2), Bambang Purwono(3*)

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


Vanillin-azine (VA), (4,4'-((1E,1'E)-hydrazine-1,2-diylidenebis(methane-lylidene))bis(2-methoxyphenol) has been synthesized from vanillin and tested as anion colorimetric chemosensors for sulfide anion. The VA was obtained from a condensation reaction between vanillin and hydrazine hydrate with a mol ratio of 2:1 mol for 24 h at room temperature. The structure was elucidated using FTIR, GC-MS, 1H-NMR, and 13C-NMR spectrometers. The VA compound was examined as a colorimetric chemosensor for sulfide anion over several anions of CN, F, Cl, Br, I, N3, CH3COO, and NO3. The structure of the product showed agreement with all spectrometric data. The VA chemosensor tests indicated only selective to S2− anion followed by a color change from colorless to light blue in a DMF:HEPES buffer solution (DMF:HBS) medium (9:1, v/v, 10 mM, pH = 7.4). Filter paper strips can detect S2− anion with a color change from white to yellow. The VA chemosensor has a limit of detection (LOD) of 5.4 × 10−4 M, therefore, the VA chemosensor can be applied to detect S2− anion in tap water.


chemosensor; colorimetry; vanillin; vanillin-azine; sulfide anion

Full Text:

Full Text PDF


[1] Kaushik, R., Ghosh, A., Singh, A., and Jose, D.A., 2018, Colorimetric sensor for the detection of H2S and its application in molecular half-subtractor, Anal. Chim. Acta, 1040, 177–186.

[2] Pla-Tolós, J., Moliner-Martínez, Y., Verdú-Andrés, J., Casanova-Chafer, J., Molins-Legua, C., and Campíns-Falcó, P., 2016, New optical paper sensor for in situ measurement of hydrogen sulphide in waters and atmosphere, Talanta, 156-157, 79–86.

[3] Shojaeifard, Z., Hemmateenejad, B., Shamsipur, M., and Ahmadi, R., 2019, Dual Fluorometric and Colorimetric Sensor Based on Quenching Effect of Copper (II) Sulfate on the Copper Nanocluster for Determination of Sulfide Ion in Water Samples, J. Photochem. Photobiol., A, 384, 112030.

[4] Zhang, H., Xia, X., Zhao, H., Zhang, G.N., Jiang, D.Y., Xue, X.Y., and Zhang, J., 2019, A near-infrared fluorescent probe based on SNAr Reaction for H2S/GSH detection in living cells and zebrafish, Dyes Pigm., 163, 183–189.

[5] Chen, G., Tang, M., Fu, X., Cheng, F., Zou, X., Wang, J., and Zeng, R., 2018, A highly sensitive and selective fluorescent sensor for detection of sulfide anion based on the steric hindrance effect, J. Mol. Struct., 1151, 230–235.

[6] Giuriati, C., Cavalli, S., Gorni, A., Badocco, D., and Pastore, P., 2004, Ion chromatographic determination of sulfide and cyanide in real matrices by using pulsed amperometric detection on a silver electrode, J. Chromatogr. A, 1023 (1), 105–112.

[7] Savizi, I.S.P., Kariminia, H.R., Ghadiri, M., and Roosta-Azad, R., 2012, Amperometric sulfide detection using Coprinus cinereus peroxidase immobilized on screen printed electrode in an enzyme inhibition based biosensor, Biosens. Bioelectron., 35 (1), 297–301.

[8] Hassan, S.S.M., Marzouk, S.A.M., and Sayour, H.E.M., 2002, Methylene blue potentiometric sensor for selective determination of sulfide ions, Anal. Chim. Acta, 466 (1), 47–55.

[9] Irmi, N.M., Purwono, B., and Anwar, C., 2021, Synthesis of symmetrical acetophenone azine derivatives as colorimetric and fluorescent cyanide chemosensors, Indones. J. Chem., 21 (6), 1337–1347.

[10] Pundi, A., Chen, J., Chang, C.J., Hseih, S.R., Lee, M.C., Chou, C.H., and Way, T.D., 2021, Naked-eye colorimetric and turn-on fluorescent Schiff base sensor for cyanide and aluminum (III) detection in food samples and cell imaging applications, Spectrochim. Acta, Part A, 262, 120139.

[11] Zheng, J., Noh, H.L., Chun, H.W., Oh, B.M., Lee, J., Choi, S.K., Kim, E., Jung, D., Lee, W.S., and Kim, J.H., 2021, Highly sensitive, selective, and rapid response colorimetric chemosensor for naked eye detection of hydrogen sulfide gas under versatile conditions: Solution, thin-film, and wearable fabric, Sens. Actuators, B, 341, 130013.

[12] Mahnashi, M.H., Mahmoud, A.M., Alkahtani, S.A., Ali, R., and El-Wekil, M.M., 2020, A novel imidazole derived colorimetric and fluorometric chemosensor for bifunctional detection of copper (II) and sulphide ions in environmental water samples, Spectrochim. Acta, Part A, 228, 117846.

[13] Wang, H., Chen, C., Liu, Y., Wu, Y., Yuan, Y., and Zhou, Q., 2019, A highly sensitive and selective chemosensor for 2,4,6-trinitrophenol based on L-cysteine-coated cadmium sulfide quantum dots, Talanta, 198, 242–248.

[14] Radchatawedchakoon, W., Sangsuwan, W., Kruanetr, S., and Sakee, U., 2014, Synthesis and evaluation of simple naked-eye colorimetric chemosensors for anions based on azo dye-thiosemicarbazones, Spectrochim. Acta, Part A, 121, 306–312.

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

[16] Zhang, H., Li, M., Zhang, C., Zhang, G., Chao, J., Shi, L., Yao, Q., Shuang, S., and Dong, C., 2019, The design of hydrogen sulfide fluorescence probe based on dual nucleophilic reaction and its application for bioimaging, Spectrochim. Acta, Part A, 207, 150–155.

[17] Li, H., Yang, Y., Wu, X., Jia, R., Zhao, P., and Wang, Y., 2021, A novel reactive chemosensor for sulfide detection with high selectivity and sensitivity based on 4-Cl coumarin derivatives, Dyes Pigm., 191, 109373.

[18] Elsayed, S., de la Torre, C., Santos-Figueroa, L.E., Marín-Hernández, C., Martínez-Máñez, R., Sancenón, F., Costero, A.M., Gil, S., and Parra, M., 2015, Azide and sulfonylazide functionalized fluorophores for the selective and sensitive detection of hydrogen sulfide, Sens. Actuators, B, 207, 987–994.

[19] Zong, L., Zhang, M., Song, Y., Xie, Y., Feng, J., Li, Q., and Li, Z., 2018, A red fluorescence probe based on naphthalene diimide for selective detection of sulfide by displacement strategy, Sens. Actuators, B, 257, 882–888.

[20] Khausik, R., Ghosh, A., and Amilan Jose, D., 2017, Recent progress in hydrogen sulphide (H2S) sensors by metal displacement approach, Coord. Chem. Rev., 347, 141–157.

[21] 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.

[22] 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.

[23] Dineshkumar, S., and Muthusamy, A, 2017, Investigation of aggregation induced emission in 4-hydroxy-3-methoxybenzaldehyde azine and polyazine towards application in (opto) electronics: Synthesis, characterization, photophysical and electrical properties, Des. Monomers Polym., 20 (1), 234–249.

[24] Li, Q., Cai, Y., Yao, H., Lin, Q., Zhu, Y.R., Li, H., Zhang, Y.M., and Wei, T.B., 2015, A colorimetric and fluorescent cyanide chemosensor based on dicyanovinyl derivatives: Utilization of the mechanism of intramolecular charge transfer blocking, Spectrochim. Acta, Part A, 136, 1047–1051.

[25] Anslyn, E.V., and Dougherty, D.A., 2006, Modern Physical Organic Chemistry, University Science Books, New York, US.

[26] Lewis, A.E., 2010, Review of metal sulphide precipitation, Hydrometallurgy, 104 (2), 222–234.

[27] Lee, S.Y., and Kim, C., 2016, A colorimetric chemosensor for sulfide in a near-perfect aqueous solution: Practical application using a test kit, RSC Adv., 6 (88), 85091–85099.


Article Metrics

Abstract views : 2575 | views : 1604

Copyright (c) 2022 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 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Analytics View The Statistics of Indones. J. Chem.