Photopolymerization of Imprinted Polymer with Dummy Template for the Recognition of Hydroquinone in Aqueous Medium

https://doi.org/10.22146/ijc.90096

Norlin Suhaiza Musali(1), Norlaili Abu Bakar(2*), Nurulsaidah Abdul Rahim(3), Wan Rusmawati Wan Mahamod(4), Norhayati Hashim(5), Sharifah Norain Mohd Sharif(6), Siti Kamilah Che Soh(7), Alizar Ulianas(8)

(1) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim 35900, Malaysia
(2) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim 35900, Malaysia
(3) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim 35900, Malaysia
(4) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim 35900, Malaysia
(5) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim 35900, Malaysia; Nanotechnology Research Centre, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim 35900, Malaysia
(6) Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim 35900, Malaysia
(7) Faculty of Science and Marine Environmental, Universiti Malaysia Terengganu, Kuala Nerus 21030, Malaysia
(8) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Negeri Padang, Jl. Prof. Dr. Hamka, Padang 25173, Indonesia
(*) Corresponding Author

Abstract


This study' purposes are to synthesize molecularly imprinted polymer (MIP) with hydroxyethyl methacrylate (HEMA) and triethylene glycol dimethacrylate (TEGDMA) using p-xylene under ultraviolet curing at 405 nm for the recognition of hydroquinone (HQ) in aqueous medium. The template was extracted from the polymer with a mixture of methanol and acetic acid (9:1) by volume (v/v). The Fourier transform infrared (FTIR) spectrum of MIP (after wash) showed the absence of peak at the range of 840–860 cm−1, which represented the stretching outside the aromatic plane C–H at the para position (p-xylene). Field emission scanning electron microscope (FESEM) micrograph showed that the MIP had cavities compared to non-imprinted polymer (NIP). The MIP (MIP-Pxy) with ratio (monomer:crosslinker) 0.25 and 1.00% template gave the highest uptake of hydroquinone (HQ) in aqueous solution, which implied more specific recognition (highest KD value). The rebinding of HQ onto MIP-Pxy was best described by both isotherm (Langmuir and Freundlich) and kinetic model (pseudo-first and -second). The MIP was successfully synthesized using p-xylene, able to recognize HQ and was very selective to p-CP. Implication of the study, the synthesized MIP can be used for recognition and sensing materials for HQ and any similar molecules.


Keywords


imprinting factor; p-xylene; phenolic compound; electron donor-acceptor; adsorbate

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References

[1] Ahmad, K., Kumar, P., and Mobin, S.M., 2020, A highly sensitive and selective hydroquinone sensor based on a newly designed N-rGO/SrZrO3 composite, Nanoscale Adv., 2 (1), 502–511.

[2] Ma, X., Liu, Z., Qiu, C., Chen, T., and Ma, H., 2013, Simultaneous determination of hydroquinone and catechol based on glassy carbon electrode modified with gold-graphene nanocomposite, Microchim. Acta, 180 (5), 461–468.

[3] Enguita, F.J., and Leitão, A.L., 2013, Hydroquinone: Environmental pollution, toxicity, and microbial answers, BioMed Res. Int., 2013 (1), 542168.

[4] Fabian, I.M., Sinnathamby, E.S., Flanagan, C.J., Lindberg, A., Tynes, B., Kelkar, R.A., Varrassi, G., Ahmadzadeh, S., Shekooh, S., and Kaye, A.D., 2023, Topical hydroquinone for hyperpigmentation: A narrative review monitoring, Cureus, 15 (11), e48840.

[5] Hammani, H., Laghrib, F., Farahi, A., Lahrich, S., El Ouafy, T., Aboulkas, A., El Harfi, K., and El Mhammedi, M.A., 2019, Preparation of activated carbon from date stones as a catalyst to the reactivity of hydroquinone: Application in skin whitening cosmetics samples, J. Sci.: Adv. Mater. Devices, 4 (3), 451–458.

[6] Santos, A., Yustos, P., Quintanilla, A., García-Ochoa, F., Casas, J.A., and Rodriguez, J.J., 2004, Evolution of toxicity upon wet catalytic oxidation of phenol, Environ. Sci. Technol., 38 (1), 133–138.

[7] Owolabi, J.O., Fabiyi, O.S., Adelakin, L.A., and Ekwerike, M.C., 2020, Effects of skin lightening cream agents - Hydroquinone and kojic acid, on the skin of adult female experimental rats, Clin., Cosmet. Invest. Dermatol., 13, 283–289.

[8] Chen, X., Wei, X., Wang, J., Yang, Y., Wang, Y., Li, Q., and Wang, S., 2020, Toxicity removal and biodegradability enhancement of sludge extract in hydroquinone-rich wastewater via cultivation of Chlorella vulgaris, J. Cleaner Prod., 277, 124030.

[9] Ibrahim, F., Sharaf El-Din, M.K., El-Deen, A.K., and Shimizu, K., 2019, A new HPLC-DAD method for the concurrent determination of hydroquinone, hydrocortisone acetate and tretinoin in different pharmaceuticals for melasma treatment, J. Chromatogr. Sci., 57 (6), 495–501.

[10] Moldovan, Z., Popa, D.E., David, I.G., Buleandra, M., and Badea, I.A., 2017, A derivative spectrometric method for hydroquinone determination in the presence of kojic acid, glycolic acid, and ascorbic acid, J. Spectrosc., 2017 (1), 6929520.

[11] Amola, L.A., Kamgaing, T., Tiegam Tagne, R.F., Atemkeng, C.D., Kuete, I.H.T., and Anagho, S.G., 2022, Optimized removal of hydroquinone and resorcinol by activated carbon based on shea residue (Vitellaria paradoxa): Thermodynamics, adsorption mechanism, nonlinear kinetics, and isotherms, J. Chem., 2022 (1), 1125877.

[12] Shengli, S., Junping, L., Qi, L., Fangru, N., Jia, F., and Shulian, X., 2018, Optimized preparation of Phragmites australis activated carbon using the Box-Behnken method and desirability function to remove hydroquinone, Ecotoxicol. Environ. Saf., 165, 411–422.

[13] Peng, Y., Tang, Z., Dong, Y., Che, G., and Xin, Z., 2018, Electrochemical detection of hydroquinone based on MoS2/reduced graphene oxide nanocomposites, J. Electroanal. Chem., 816, 38–44.

[14] Sun, X., Xie, Y., Chu, H., Long, M., Zhang, M., Wang, Y., and Hu, X., 2022, A highly sensitive electrochemical biosensor for the detection of hydroquinone based on a magnetic covalent organic framework and enzyme for signal amplification, New J. Chem., 46 (24), 11902–11909.

[15] Karthika, A., Ramasamy Raja, V., Karuppasamy, P., Suganthi, A., and Rajarajan, M., 2020, A novel electrochemical sensor for determination of hydroquinone in water using FeWO4/SnO2 nanocomposite immobilized modified glassy carbon electrode, Arabian J. Chem., 13 (2), 4065–4081.

[16] Wang, Y., Liu, Y., and Yang, M., 2020, Molecularly imprinted electrochemiluminescence sensor for sensitive and selective detection of hydroquinone molecularly imprinted electrochemiluminescence sensor for sensitive and selective detection of hydroquinone, Chem. Lett., 49 (7), 855–858.

[17] Shafqat, S.R., Bhawani, S.A., Bakhtiar, S., and Ibrahim, M.N.M., 2020, Synthesis of molecularly imprinted polymer for removal of Congo red, BMC Chem., 14 (1), 27.

[18] Malik, M.I., Shaikh, H., Mustafa, G., and Bhanger, M.I., 2019, Recent applications of molecularly imprinted polymers in analytical chemistry, Sep. Purif. Rev., 48 (3), 179–219.

[19] Bates, F., Busato, M., Piletska, E., Whitcombe, M.J., Karim, K., Guerreiro, A., del Valle, M., Giorgetti, A., and Piletsky, S., 2017, Computational design of molecularly imprinted polymer for direct detection of melamine in milk, Sep. Sci. Technol., 52 (8), 1441–1453.

[20] Cheong, W.J., Yang, S.H., and Ali, F., 2013, Molecular imprinted polymers for separation science: A review of reviews, J. Sep. Sci., 36 (3), 609–628.

[21] Sajini, T., Gigimol, M.G., and Mathew, B., 2019, A brief overview of molecularly Imprinted polymers supported on titanium dioxide matrices, Mater. Today Chem., 11, 283–295.

[22] Cui, Y., He, Z., Xu, Y., Su, Y., Ding, L., and Li, Y., 2020, Fabrication of molecularly imprinted polymers with tunable adsorption capability based on solvent-responsive, Chem. Eng. J., 405, 126608.

[23] Poole, C.F., and Poole, S.K., 2012, “Principles and Practice of Solid-Phase Extraction” in Comprehensive Sampling and Sample Preparation, Eds. Pawliszyn, J., Academic Press, Oxford, UK, 273–297.

[24] Shen, Y., Miao, P., Liu, S., Gao, J., Han, X., Zhao, Y., and Chen, T., 2023, Preparation and application progress of imprinted polymers, Polymers, 15 (10), 2344.

[25] Pupin, R.R., Foguel, M.V., Gonçalves, L.M., and Sotomayor, M.P.T., 2020, Magnetic molecularly imprinted polymers obtained by photopolymerization for selective recognition of penicillin G, J. Appl. Polym. Sci., 137 (13), 48496.

[26] Kan, X., Zhao, Q., Zhang, Z., Wang, Z., and Zhu, J.J., 2008, Molecularly imprinted polymers microsphere prepared by precipitation polymerization for hydroquinone recognition, Talanta, 75 (1), 22–26.

[27] Singh, R., and Singh, M., 2022, Highly selective and specific monitoring of pollutants using dual template imprinted MIP sensor, J. Electroanal. Chem., 926, 116939.

[28] Shafqat, S.R., Bhawani, S.A., Bakhtiar, S., Ibrahim, M.N.M., and Shafqat, S.S., 2023, Template-assisted synthesis of molecularly imprinted polymers for the removal of methyl red from aqueous media, BMC Chem., 17 (1), 46.

[29] Yu, H., He, Y., She, Y., Wang, M., Yan, Z., Ren, J.H., Cao, Z., Shao, Y., Wang, S., Abd El-Aty, A.M., Hacımüftüoğlu, A., and Wang, J., 2019, Preparation of molecularly imprinted polymers coupled with high-performance liquid chromatography for the selective extraction of salidroside from Rhodiola crenulata, J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 1118-1119, 180–186.

[30] Hasanah, A.N., Susanti, I., Marcellino, M., Maranata, G.J., Saputri, F.A., and Pratiwi, R., 2021, Microsphere molecularly imprinted solid-phase extraction for diazepam analysis using itaconic acid as a monomer in propanol, Open Chem., 19 (1), 604–613.

[31] Edet, U.A., and Ifelebuegu, A.O., 2020, Kinetics, isotherms, and thermodynamic modeling of the adsorption of phosphates from model wastewater using recycled brick waste, Process, 8 (6), 665.

[32] Langmuir, I., 1918, The adsorption of gases on plane surfaces of glass, mica and platinum, J. Am. Chem. Soc., 40 (9), 1361–1403.

[33] Szczepaniak, W., Zabłocka-Malicka, M., Pasiecznik, I., Pohl, P., and Rutkowski, P., 2018, Adsorption of La3+ and Dy3+ ions on biohydroxyapatite obtained from pork bones gasified with steam, Environ. Prot. Eng., 44 (1), 29–40.

[34] Pizan-aquino, C., Wong, A., Avilés-Félix, L., Khan, S., Picasso, G., and Sotomayor, M.D.P.T., 2020, Evaluation of the performance of selective M-MIP to tetracycline using electrochemical and HPLC-UV method, Mater. Chem. Phys., 245, 122777.

[35] Desta, M.B., 2013, Batch sorption experiments: Langmuir and Freundlich isotherm studies for the adsorption of textile metal ions onto teff straw (Eragrostis tef) agricultural waste, J. Thermodyn., 2013 (1), 375830.

[36] Sun, M., Li, Y., Sha, S., Gao, J., Wang, R., Zhang, Y., Hao, Q., Chen, H., Yao, Q., and Ma, X., 2020, The composition and structure of n-hexane insoluble-hot benzene soluble fraction and hot benzene insoluble fraction from low temperature coal tar, Fuel, 262, 116511.

[37] Liu, Y., Wang, Q., Guo, S., Jia, P., Shui, Y., Yao, S., Huang, C., Zhang, M., and Wang, L., 2018, Highly selective and sensitive fluorescence detection of hydroquinone using novel silicon quantum dots, Sens. Actuators, B, 275, 415–421.

[38] Sharma, G., and Kandasubramanian, B., 2020, Molecularly imprinted polymers for selective recognition and extraction of heavy metal ions and toxic dyes, J. Chem. Eng. Data, 65 (2), 396–418.

[39] Shim, D.Y., Chang, S.M., and Kim, J.M., 2021, Development of fast resettable gravimetric aromatic gas sensors using quartz crystal microbalance, Sens. Actuators, B, 329, 129143.

[40] Tolkou, A.K., Kyzas, G.Z., and Katsoyiannis, I.A., 2022, Arsenic(III) and Arsenic(V) removal from water sources by molecularly imprinted polymers (MIPs): A mini review of recent developments, Sustainability, 14 (9), 5222.

[41] Limthin, D., Klamchuen, A., and Phromyothin, D., 2019, Surface modification of superparamagnetic iron oxide nanoparticles and methyl methacrylate molecularly imprinted polymer for gluten detection, Ferroelectrics, 552 (1), 97–107.

[42] Bakhtiar, S., Bhawani, S.A., and Shafqat, S.R., 2019, Synthesis and characterization of molecular imprinting polymer for the removal of 2-phenylphenol from spiked blood serum and river water, Chem. Biol. Technol. Agric., 6 (1), 15.

[43] Retnaningtyas, Y., Supriyanto, G., Tri Puspaningsih, N.N., Irawan, R., and Siswodihardjo, S., 2021, A novel molecular imprinting polymer for the selective adsorption of D-arabinitol from spiked urine, Turk. J. Chem., 44 (6), 1265–1277.

[44] Guo, P., Yang, W., Hu, H., Wang, Y., and Li, P., 2019, Rapid detection of aflatoxin B1 by dummy template molecularly imprinted polymer capped CdTe quantum dots, Anal. Bioanal. Chem., 411 (12), 2607–2617.

[45] Masumoto, S., Nakamura, Y., and Haginaka, J., 2021, Molecularly imprinted polymers for arbutin and rutin by modified precipitation polymerization and their application for selective extraction of rutin in nutritional supplements, J. Pharm. Biomed. Anal., 205, 114294.

[46] Comeau, P.A., and Willett, T.L., 2020, Triethyleneglycol dimethacrylate addition improves the 3D-printability and construct properties of a GelMA-nHA composite system towards tissue engineering applications, Mater. Sci. Eng., C, 112, 110937.

[47] Rubahamya, B., Kumar Reddy, K.S., Prabhu, A., Al Shoaibi, A., and Srinivasakannan, C., 2019, Porous carbon screening for benzene sorption, Environ. Prog. Sustain. Energy, 38 (S1), 93–99.

[48] Grissom, T.G., Sharp, C.H., Usov, P.M., Troya, D., Morris, A.J., and Morris, J.R., 2018, Benzene, toluene, and xylene transport through UiO-66: Diffusion rates, energetics, and the role of hydrogen bonding, J. Phys. Chem. C, 122 (28), 16060–16069.

[49] Mohanadas, D., Tukimin, N., and Sulaiman, Y., 2019, Simultaneous electrochemical detection of hydroquinone and catechol using poly(3,4-ethylenedioxythiophene)/reduced graphene oxide/manganese dioxide, Synth. Met., 252, 76–81.

[50] Loreto, S., Cuypers, B., Brokken, J., Van Doorslaer, S., De Wael, K., and Meynen, V., 2017, The effect of the buffer solution on the adsorption and stability of horse heart myoglobin on commercial mesoporous titanium dioxide: A matter of the right choice, Phys. Chem. Chem. Phys., 19, 13503.

[51] Cantarella, M., Carroccio, S.C., Dattilo, S., Avolio, R., Castaldo, R., Puglisi, C., and Privitera, V., 2019, Molecularly imprinted polymer for selective adsorption of diclofenac from contaminated water, Chem. Eng. J., 367, 180–188.

[52] Anirudhan, T.S., and Anju, S.M., 2019, Synthesis and evaluation of TiO2 nanotubes/silylated graphene oxide-based molecularly imprinted polymer for the selective adsorption and subsequent photocatalytic degradation of 2,4-dichlorophenoxyacetic, J. Environ. Chem. Eng., 7 (5), 103355.

[53] Amatatongchai, M., Sitanurak, J., Sroysee, W., Sodanat, S., Chairam, S., Jarujamrus, P., Nacapricha, D., and Lieberzeit, P.A., 2019, Highly sensitive and selective electrochemical paper-based device using a graphite screen-printed electrode modified with molecularly imprinted polymers coated Fe3O4@Au@SiO2 for serotonin determination, Anal. Chim. Acta, 1077, 255–265.

[54] Wang, X., Wang, M., Wu, B., Yu, S., Liu, Z., Qin, X., Xu, H., Li, W., Luo, S., Wang, L., Ma, C., and Liu, S., 2024, Magnetic molecularly imprinted polymers using ternary deep eutectic solvent as novel functional monomer for hydroxytyrosol separation, Heliyon, 10 (8), e28257.

[55] Hanbali, G., Jodeh, S., Hamed, O., Bol, R., Khalaf, B., Qdemat, A., Samhan, S., and Dagdag, O., 2020, Magnetic multiwall carbon nanotube decorated with novel functionalities: Synthesis and application as adsorbents for lead removal from aqueous medium, Processes, 8 (8), 986.

[56] Khoo, W.C., Kamaruzaman, S., Lim, H.N., Md. Jamil, S.N.A., and Yahaya, N., 2019, Synthesis and characterization of graphene oxide-molecularly imprinted polymer for Neopterin adsorption study, J Polym Res., 26 (8), 184.

[57] Bagheri, A.R., Aramesh, N., Khan, A.A., Gul, I., Ghotekar, S., and Bilal, M., 2021, Molecularly imprinted polymers-based adsorption and photocatalytic approaches for mitigation of environmentally-hazardous pollutants - A review, J. Environ. Chem. Eng., 9 (1), 104879.

[58] Rajadhiraj, R., and Nandiyanto, A.B.D., 2022, Curcumin adsorption on zinc imidazole framework-8 particles: Isotherm adsorption using Langmuir, Freundlich, Temkin, and Dubinin-Radushkevich models, J. Eng. Sci. Technol., 17 (2), 1078–1089.

[59] Hou, L., Han, X., and Wang, N., 2020, High performance of molecularly imprinted polymer for the selective adsorption of erythromycin in water, Colloid. Polym. Sci., 298 (8), 1023–1033.

[60] Li, Y., Wang, Y., Wang, M., Zhang, J., Wang, Q., and Li, H., 2020, A molecularly imprinted nanoprobe incorporating Cu2O@Ag nanoparticles with different morphologies for selective SERS based detection of chlorophenols, Microchim. Acta, 187 (1), 59.

[61] Zhang, Z., Sun, D., Li, G., Zhang, B., Zhang, B., Qiu, S., Li, Y., and Wu, T., 2019, Calcined products of Mg–Al layered double hydroxides/single-walled carbon nanotubes nanocomposites for expeditious removal of phenol and 4-chlorophenol from aqueous solutions, Colloids Surf., A, 565, 143–153.



DOI: https://doi.org/10.22146/ijc.90096

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