Synthesis of Pyridine Derivative-based Chemosensor for Formaldehyde Detection

Nurul Hidayah(1), Bambang Purwono(2*), Beta Achromi Nurohmah(3), Harno Dwi Pranowo(4)

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


Compound of 3,3'-(4-(2-amino-4,5-dimethoxyphenyl)pyridine-2,6-diyl)dianiline (CHP) has been synthesized via three-step synthetic procedure from veratraldehyde as starting material and 4-(4,5-dimethoxy-2-nitrophenyl)-2,6-bis(3-nitrophenyl)pyridine (CHP-1) as an intermediate compound. The CHP-1 was reduced using hydrazine hydrate catalyzed by 10% Pd/C to the final target of CHP. The spectroscopic study revealed that CHP in acetonitrile could detect formaldehyde through fluorescence enhancement and showed color change from yellow to blue under the 365 nm portable ultraviolet lamp as a response. Based on the fluorescence spectra, the emission wavelength of CHP in acetonitrile was shifted from 526 to 480 nm after addition of formaldehyde. Limit detection (LOD), selectivity, sensitivity, and computational study geometry of CHP as a chemosensor for formaldehyde has also been investigated. CHP could also be applied as a test paper for the detection of formaldehyde qualitatively.


pyridine; chemosensor; formaldehyde; fluorescence

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[1] Nowshad, F., Islam, M.N., and Khan, M.S., 2018, Concentration and formation behavior of naturally occurring formaldehyde in foods, Agric. Food Secur., 7 (1), 17.

[2] Merk, O., and Speit, G., 1998, Significance of formaldehyde-induced DNA-protein crosslinks for mutagenesis, Environ. Mol. Mutagen., 32 (3), 260–268.

[3] Cogliano, V.J., Grosse, Y., Baan, R.A., Straif, K., Secretan, M.B., and El Ghissassi, F., 2005, Summary of IARC monographs on formaldehyde 2-butoxyethanol and 1-tert-butoxy-2-propanol, Environ. Health Perspect., 113 (9), 1205–1208.

[4] Li, J., Zhu, L., and Ye, L., 2007, Determination of formaldehyde in squid by high-performance liquid chromatography, Asia Pac. J. Clin. Nutr., 16 (Suppl. 1), 127–130.

[5] Yeh, T.S., Lin, T.C., Chen, C.C., and Wen, H.M., 2013, Analysis of free and bound formaldehyde in squid and squid products by gas chromatography-mass spectrometry, J. Food Drug Anal., 21 (2), 190–197.

[6] Korpan, Y.I., Gonchar, M.V., Starodub, N.F., Shulga, A.A., Sibirny, A.A., and Elskaya, A.V., 1993, A cell biosensor specific for formaldehyde based on pH- sensitive transistors coupled to methylotrophic yeast cells with genetically adjusted metabolism, Anal. Biochem., 215 (2), 216–222.

[7] Nikitina, O., Shleev, S., Gayda, G., Demkiv, O., Gonchar, M., Gorton, L., Csöregi E., and Nistor M., 2007, Bi-enzyme biosensor based on NAD+- and glutathione-dependent recombinant formaldehyde dehydrogenase and diaphorase for formaldehyde assay, Sens. Actuators, B, 125, 1–9.

[8] Dar, A., Shafique, U., Anwar, J., Zaman, W., and Naseer, A., 2016, A simple spot test quantification method to determine formaldehyde in aqueous samples, J. Saudi Chem. Soc., 20 (Suppl. 1), S352–S356.

[9] Mohr, G.J., 2003, New chromoreactands for the detection of aldehydes, amines and alcohols, Sens. Actuators, B, 90 (1-3), 31–36.

[10] Wei, K., Ma, L., Ma, G., Ji, C., and Yin, M., 2019, A two-step responsive colorimetric probe for fast detection of formaldehyde in weakly acidic environment, Dyes Pigm., 165, 294–300.

[11] Song, H., Rajendiran, S., Kim, N., Jeong, S.K., Koo, E., Park, G., Thangadurai, T.D., and Yoon, S., 2012, A tailor designed fluorescent ‘turn-on’ sensor of formaldehyde based on the BODIPY motif, Tetrahedron Lett., 53 (37), 4913–4916.

[12] Zhou, W., Dong, H., Yan, H., Shi, C., Yu, M., Wei, L., and Li, Z., 2015, HCHO-reactive molecule with dual-emission-enhancement property for quantitatively detecting HCHO in near 100% water solution, Sens. Actuators, B, 209, 664–669.

[13] Liu, C., Shi, C., Li, H., Du, W., Li, Z., Wei, L., and Yu, M., 2015, Nanomolar fluorescent quantitative detection of formaldehyde with a 8-hydroxyquinoline derivative in aqueous solution and electrospun nanofibers, Sens. Actuators, B, 219, 185–191.

[14] Roth, A., Li, H., Anorma, C., and Chan, J., 2015, A reaction-based fluorescent probe for imaging of formaldehyde in living cells, J. Am. Chem. Soc., 137 (34), 10890–10893.

[15] Dong, B., Song, X., Tang, Y., and Lin, W., 2016, A rapid and facile fluorimetric method for detecting formaldehyde, Sens. Actuators, B, 222, 325–330.

[16] Zhou, Y., Yan, J., Zhang, N., Li, D., Xiao, S., and Zheng, K., 2018, A ratiometric fluorescent probe for formaldehyde in aqueous solution, serum and air using aza-cope reaction, Sens. Actuators, B, 258, 156–162.

[17] Bi, A., Gao, T., Cao, X., Dong, J., Liu, M., Ding, N., Liao, W., and Zeng, W., 2018, A novel naphthalimide-based probe for ultrafast, highly selective and sensitive detection of formaldehyde, Sens. Actuators, B, 255, 3292–3297.

[18] Li, Q., Oshima, M., and Motomizu, S., 2007, Flow-injection spectrofluorometric determination of trace amounts of formaldehyde in water after derivatization with acetoacetanilide, Talanta, 72 (5), 1675–1680.

[19] Indang, M.N., Abdulamir, A.S., Bakar, A.A., Salleh, A.B., Lee, Y.H., and Azah, Y.N., 2009, A review: Methods of determination of health-endangering formaldehyde in diet, Res. J. Pharmacol., 3 (2), 31–47.

[20] Chen, Y., Shi, W., Hui, Y., Sun, X., Xu, L., Feng, L., and Xie, Z., 2015, A new highly selective fluorescent turn-on chemosensor for cyanide anion, Talanta, 137, 38–42.

[21] Ovianto, D., Sugiharta, I.B.A.R., and Purwono, B., 2017, Synthesis of 4-phenyl-2,6-bis(4-aminophenyl)pyridine compound and study of their fluorescence behaviour for formaldehyde sensing, Int. J. ChemTech Res., 10 (9), 918–923.

[22] Tamami, B., and Yeganeh, H., 2001, Synthesis and characterization of novel aromatic polyamides derived from 4-aryl-2,6-bis(4-aminophenyl) pyridines, Polymer, 42 (2), 415–420.

[23] He, L., Yang, X., Ren, M., Kong, X., Liu, Y., and Lin, W., 2016, An ultra-fast illuminating fluorescent probe for monitoring formaldehyde in living cells, shiitake mushrooms, and indoors, Chem. Commun., 52 (61), 9582–9585.

[24] Joshi, B.P., Park, J., Lee, W.I., and Lee, K.H., 2009, Ratiometric and turn-on monitoring for heavy and transition metal ions in aqueous solution with a fluorescent peptide sensor, Talanta, 78 (3), 903–909.


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