Synthesis and Dielectric-Antimicrobial Properties of Poly(n-Butyl Methacrylate) with Chalcone Initiator

Öz

In this study, in the first stage, chalcone compound was synthesized in accordance with the literature. Then, the synthesized chalcone compound was reacted with bromine acetylbromide and the initiator used in the ATRP method was synthesized. The characterization of the synthesized compound was carried out by FT-IR and NMR spectrometers. In the second stage, the synthesized chalcone compound was used as an initiator and the polymerization of n-butyl methacrylate monomer was provided by ATRP method. In the last stage, the dielectric and antimicrobial properties of the polymer were investigated. Agar well method was used in the antimicrobial study. Dielectric properties were investigated as a function of frequency between 100 Hz and 5000 Hz at room temperature.

Anahtar Kelimeler

• Chalcone
• ATRP
• Antimicrobial Properties
• Dielectric Properties

Poli(n-Bütil Metakrilat)'ın Kalkon Başlatıcısı ile Sentezi ve Dielektrik-Antimikrobiyal Özellikleri

Öz

Bu çalışmada, ilk aşamada, literatüre uygun şekilde kalkon bileşiği sentezlenmiştir. Daha sonra sentezlenen kalkon bileşiği ile brom asetilbromür ile tepkimeye sokularak ATRP metodunda kullanılan başlatıcı sentezi gerçekleştirilmiştir. Sentezlenen bileşiğin karakterizasyonu, FT-IR ve NMR spektrometreleri ile yapılmıştır. İkinci aşamada, Sentezlenen kalkon bileşiği başlatıcı olarak kullanılarak ATRP metodu ile n-bütil metakrilat monomerinin polimerleşmesi sağlanmıştır. Son aşamada ise polimerin dielektrik ve antimikrobiyal özelliği incelenmiştir. Antimikrobiyal çalışmada Agar kuyu yöntemi kullanılmıştır. Dielektrik özellikleri, oda sıcaklığında 100 Hz ile 5000 Hz aralığında frekansın bir fonksiyonu olarak incelenmiştir.

Anahtar Kelimeler

• Kalkon
• ATRP
• Antimikrobial Özellikler
• Dielektrik Özellikler

Kaynakça

1. Saçak, M., Polymer Chemistry, Gazi Bookstore, Ankara, Turkey, 2004.
2. Köroğlu, A.M., Synthesis, characterization and copolymerization of new methacrylate monomers and polymers carrying oxime esters in the minor branch, Afyon Kocatepe University, Master Thesis, Afyon, 2006.
3. Opletalova, V., Hartl, J., Palat, K.Jr., Patel, A., Conformational analysis of 2-hydroxy-2',5'-diazachalcones, Journal of Pharmaceutical and Biomedical Analysis, 23, 55–59, 2020.
4. Indira, J., Karat, P.P., Sarojini, B.K., Growth, characterization, and nonlinear optical property of chalcone derivative, Journal of Crystal Growth, 242, 209–214. 2002.
5. He, Z., Li, D., Hensley, D.K., Rondione, A.J., Chen, J., Switching phase separation mode by varying the hydrophobicity of polymer additives in solution-processed semiconducting small-molecule/polymer blends, Applied Physics Letters, 103, 113301, 2013.
6. He, Z., Chen, J., Keum, J.K., Szulczewski, G., Li, D., Improving performance of TIPS pentacene-based organic thin film transistors with small-molecule additives, Org Electron 15, 150–155, 2014.
7. Şentürk, A., The Synthesis and Characterization of Methacrylate Polymers Bearing Chalcone, Master’s Thesis, Firat University, Elazig, Turkey, 2011.
8. Ekbote, A.N., Maidur, S.R., Jahagirdar, J.R., Patil, P.S., Soma, V.R., Femtosecond nonlinear optical investigations of nitro chalcones-doped PMMA thin films for optical limiting and photonic applications, Materials Today Communications, 37, 107240, 2023.

9. Fang, X., Yang, B., Cheng, Z., Zhang, P., Yang, M., Synthesis and antimicrobial activity of novel chalcone derivatives, Research on Chemical Intermediates, 40, 1715–1725, 2014.
10. Sudhakar, C., Suresh, J., Valarmathi, N., Sumathi, S., Karthikeyan, A., et al., Synthesis, characterization of acrylate polymer having chalcone moiety: evaluation of antimicrobial, anticancer and drug release study, Journal Of Biomaterials Science-Polymer Edition, 32(4), 438–453, 2020.
11. Bonesi, M., Loizzo, M.R., Statti, G.A., Michel, S., Tillequin, F., Menichini, F., The synthesis and Angiotensin Converting Enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives, Bioorganic & Medicinal Chemistry Letters, 20(6), 1990–1993, 2010.
12. Burmaoglu, S., Algul, O., Anıl, D.A., Gobek, A., Duran, G.G., Ersan, R.H., et al., Synthesis and anti-proliferative activity of fluoro-substituted chalcones, Bioorganic & Medicinal Chemistry Letters, 26(13), 3172–3176, 2016.
13. Shenvi, S., Kumar, K., Hatti, K.S., Rijesh, K., Diwakar, L., Reddy, G.C., Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure-activity relationship, European Journal of Medicinal Chemistry, 62, 435–442, 2013.
14. Hsieh, C.T., Hsieh, T.J., El-Shazly, M., Chuang, D.W., Tsai, Y.H., Yen, C.T., et al., Synthesis of chalcone derivatives as potential anti-diabetic agents. Bioorganic & Medicinal Chemistry Letters, 22(12), 3912–3915, 2012.
15. Iqbal, H., Prabhakar, V., Sangith, A., Chandrika, B., Balasubramanian, R., Synthesis, anti-inflammatory and antioxidant activity of ring-A-monosubstituted chalcone derivatives, Medicinal Chemistry Research, 23, 4383–4394, 2014.
16. Sashidhara, K.V., Avula, S.R., Mishra, V., Palnati, G.R., Singh, L.R., Singh, N., Chhonker, et al., Identification of quinoline-chalcone hybrids as potential antiulcer agents, European journal of medicinal chemistry, 89, 638–653, 2015.
17. Pingaew, R., Saekee, A., Mandi, P., Nantasenamat, C., Prachayasittikul, S., Ruchirawat, S., et al., Synthesis, biological evaluation and molecular docking of novel chalcone–coumarin hybrids as anticancer and antimalarial agents, European Journal of Medicinal Chemistry, 85, 65–76, 2014.
18. Shi, F., Fang, H., Xu, W., Design, synthesis and biological activity of novel chalcone derivatives as anti-influenza agents, Chemical Research in Chinese Universities, 32(1), 28–34, 2016.
19. Mahapatra, D., Asati, V., Bharti, S.K., Recent therapeutic progress of chalcone scaffold bearing compounds as prospective anti-gout candidates, Journal of Critical Reviews, 6(1), 1–5, 2019.
20. Demirelli, K., Kaya, E., Coşkun, M., Bagci, E., Thermal degradation of two different polymers bearing amide pendant groups prepared by ATRP method, Journal of Thermal Analysis and Calorimetry, 114(2), 917–926, 2013.
21. Jobish, J., Charoen, N., Praveen, P., Dielectric properties and AC conductivity studies of novel NR/PVA full-interpenetrating polymer networks, Journal of Non-Crystalline Solids, 358(8), 1113–1119, 2012.
22. Kamath, A., Devendrappa, H., Concentration-dependent ionic conductivity and dielectric relaxation of methyl blue-dyed polyethylene oxide films, Polymer Bulletin, 72(10), 2705–2724, 2015.
23. Coşkun D., The Synthesis of Benzofurane Substituted α,β-Unsaturated Ketones and Their Derivatives, PhD Thesis, Firat University, Elazig, Turkey, 2008.
24. Arslan Ateşşahi̇n, D., Kadioğlu Dalkiliç, L., Özeren, Y., Dalkiliç, S., Çakmak, K., et al., Investigation of Cytotoxic, Antimicrobial and Antioxidant Activity of Echium vulgare L. Seed, International Journal of Nature and Life Sciences, 7(2), 129–135, 2023.
25. Dalkılıç, S., Kadıoğlu Dalkılıç, L., Korkmaz, İ., Antimicrobial Effect of Traditional Breakfast Zahter, Gumuşhane University Science Institute Journal, 10(1), 128–133, 2020.
26. Baliyan, S., Mukherjee, R., Priyadarshini, A., Vibhuti, A., Gupta, A., Pandey, R. P., et al., Determination of Antioxidants by DPPH Radical Scavenging Activity and Quantitative Phytochemical Analysis of Ficus religiosa, Molecules, 27(4), 1326, 2022.
27. Çavuş, M.S., Defect-Assisted Fractional Stochastic Ising Model of Dielectric Relaxation, Çukurova University, PhD Thesis, Adana, 2010.