Colorimetric Chemosensor for Sulfide Anion Detection Based on Symmetrical Nitrovanillin Azine

https://doi.org/10.22146/ijc.71259

Diana Lestari(1), Tutik Dwi Wahyuningsih(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

Abstract


The nitrovanillin azine (NA) has been successfully synthesized and examined as a colorimetric chemosensor for sulfide anion detection. The NA was synthesized using two steps reaction. Vanillin was reacted with concentrated nitric acid to form 5-nitrovanillin (NV) then the NV was condensed with hydrazine hydrate to produce the NA. The NA was obtained and fully elucidated by FTIR, 1H-NMR, 13C-NMR, and GC-MS spectrometer. The NA activity for anionic chemosensor was then carried out on several anions such as F⁻, Cl⁻, Br⁻, I⁻, S2⁻, CN⁻, HCO3⁻, AcO⁻, H2PO4⁻, N3⁻, NO2⁻, SCN⁻, ClO3⁻, and NO3⁻. The chemosensor tests showed NA was only selective for S2− in DMF:HEPES buffer (9:1, v/v, 10 mM, pH = 7.4) giving color change from light yellow to dark green. The LOD value was 1.43 × 10−5 M and the interaction model of NA-S2− indicated deprotonation mode between the -OH group with sulfide anion in a ratio of 1:1. The NA chemosensor can be applied for qualitatively analysis of sulfide anion using filter paper strips and quantitatively analysis of sulfide anion in tap water.

Keywords


5-nitrovanillin; hydrazine; azine; colorimetric; chemosensor

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References

[1] Hammers, M.D., Taormina, M.J., Cerda, M.M., Montoya, L.A., Seidenkranz, D.T., Parthasarathy, R., and Pluth, M.D., 2015, A bright fluorescent probe for H2S enables analyte-responsive, 3d imaging in live zebrafish using light sheet fluorescence microscopy, J. Am. Chem. Soc., 137 (32), 10216–10223.

[2] Han, Y., Qin, J., Chang, X., Yang, J., and Du, J., 2006, Hydrogen sulfide and carbon monoxide are in synergy with each other in the pathogenesis of recurrent febrile seizures, Cell. Mol. Neurobiol., 26 (1), 101–107.

[3] Lou, Z., Li, P., and Han, K., 2015, “Selenium as a Versatile Center in Fluorescence Probe for the Redox Cycle Between HClO Oxidative Stress and H2S Repair” in Advanced Protocols in Oxidative Stress III, Eds. Armstrong, D., Springer New York, 97–110.

[4] Chan, Y.H., Lock, S.S.M., Wong, M.K., Yiin, C.L., Loy, A.C.M., Cheah, K.W., Chai, S.Y.W., Li, C., How, B.S., Chin, B.L.F., Chan, Z.P., and Lam, S.S., 2022, A state-of-the-art review on capture and separation of hazardous hydrogen sulfide (H2S): Recent advances, challenges and outlook, Environ. Pollut., 314, 120219.

[5] Dufton, N., Natividad, J., Verdu, E.F., and Wallace, J.L., 2012, Hydrogen sulfide and resolution of acute inflammation: A comparative study utilizing a novel fluorescent probe, Sci. Rep., 2 (1), 499.

[6] Pol, R., Céspedes, F., Gabriel, D., and Baeza, M., 2019, Fully integrated screen-printed sulfide-selective sensor on a 3D-printed potentiometric microfluidic platform, Sens. Actuators, B, 290, 364–370.

[7] Shu, J., Qiu, Z., and Tang, D., 2018, Self-referenced smartphone imaging for visual screening of H2S using CuxO-polypyrrole conductive aerogel doped with graphene oxide framework, Anal. Chem., 90 (16), 9691–9694.

[8] Satheshkumar, A., El-Mossalamy, E.H., Manivannan, R., Parthiban, C., Al-Harbi, L.M., Kosa, S., and Elango, K.P., 2014, Anion induced azo-hydrazone tautomerism for the selective colorimetric sensing of fluoride ion, Spectrochim. Acta, Part A, 128, 798–805.

[9] Wang, Q., Wang, Y., Guan, M., Zhu, S., Yan, X., Lei, Y., Shen, X., Luo, L., and He, H., 2020, A multicolor colorimetric assay for sensitive detection of sulfide ions based on anti-etching of triangular gold nanoplates, Microchem. J., 159, 105429.

[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] Rajamanikandan, R., and Ilanchelian, M., 2022, Simple smartphone merged rapid colorimetric platform for the environmental monitoring of toxic sulfide ions by cysteine functionalized silver nanoparticles, Microchem. J., 174, 107071.

[12] Tiwari, K., Kumar, S., Kumar, V., Kaur, J., Arora, S., and Mahajan, R.K., 2018, An azine based sensor for selective detection of Cu2+ ions and its copper complex for sensing of phosphate ions in physiological conditions and in living cells, Spectrochim. Acta, Part A, 191, 16–26.

[13] 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.

[14] Irmi, M.N., 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.

[15] 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, 178–186.

[16] Rokhmah, N.V., Mardjan, M.I.D., and Purwono, B., 2022, Synthesis vanillin-azine as colorimetric chemosensor of sulfide anion, Indones. J. Chem., 22 (6), 1490–1500.

[17] Li, J.Z., Leng, T.H., Wang, Z.Q., Zhou, L., Gong, X.Q., Shen, Y.J., and Wang, C.Y., 2019, A large Stokes shift, sequential, colorimetric fluorescent probe for sensing Cu2+/S2− and its applications, J. Photochem. Photobiol., A, 373, 146–153.

[18] Rahmawati, R., Purwono, B., and Matsjeh, S., 2018, A naked-eye colorimetric receptor for anions based on nitro group featuring with benzimidazole unit, Asian J. Chem., 30 (9), 1933–1936.

[19] 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.

[20] Ghosh, T., and Mishra, S., 2020, A natural cyanobacterial protein C-phycoerythrin as an HS selective optical probe in aqueous systems, Spectrochim. Acta, Part A, 239, 118469.

[21] Tan, B., Jin, S., Sun, J., Gu, Z., Sun, X., Zhu, Y., Huo, K., Cao, Z., Yang, P., Xin, X., Liu, X., Pan, L., Qiu, F., Jiang, J., Jia, Y., Ye, F., Xie, Y., and Zhu, Y.Z., 2017, New method for quantification of gasotransmitter hydrogen sulfide in biological matrices by LC-MS/MS, Sci. Rep., 7, 46278.

[22] Kamli, S., Orojloo, M., and Amani, S., 2021, Design and synthesis of a novel chemosensor for simultaneous detection of CN, HCO3 and AcO anions and Fe2+ cation in an organic-aqueous environment: An experimental and Density Functional Theory studies, J. Mol. Struct., 1234, 130708.

[23] Migdisov, A.A., Williams-Jones, A.E., Lakshtanov, L.Z., and Alekhin, Y.V., 2002, Estimates of the second dissociation constant of H2S from the surface sulfidation of crystalline sulfur, Geochim. Cosmochim. Acta, 66 (10), 1713–1725.

[24] Kang, J.H., Chae, J.B., and Kim, C., 2018, A multi-functional chemosensor for highly selective ratiometric fluorescent detection of silver(I) ion and dual turn-on fluorescent and colorimetric detection of sulfide, R. Soc. Open Sci., 5 (6), 180293.

[25] Official Methods of Analysis of AOAC International, 2019, AOAC Guidelines for Single-Laboratory Validation of Chemical Methods for Dietary Supplements and Botanicals, AOAC International, Gaithersburg, MD, USA, 1–15.



DOI: https://doi.org/10.22146/ijc.71259

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