Abstract
In this study, first the chalcone compounds abbreviated as CHAL-F, CHAL-Cl and CHAL-Br containing the halogen group in the side chain were synthesized in medium alkaline at 0 °C. Then, chalcone methacrylamide monomers abbreviated as M-F, M-Cl and M-Br containing halogen group in side chain were synthesized by the reaction of the chalcone compounds with methacryloylchloride at 0–5 °C in the presence of triethylamine (E3N). The chalcone methacrylamide polymers abbreviated as P-F, P-Cl and P-Br were prepared by the free radical polymerization at 70 °C, in DMF solution and by 2,2ʹ-azobisizobutyronitrile (AIBN) initiator. The structures of synthesized compounds were characterized by FTIR, UV–Vis and 1H-13C-NMR. Thermal characterizations of polymers were performed by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The glass transition temperature (Tg) of P-F, P-Cl and P-Br was found at 103, 129 and 110 °C, respectively, from DSC measurements. According to the Flynn–Wall–Ozawa (FWO) method, the average decomposition activation energy of the P-Br was found as 76.84 kJ mol−1 from the TGA thermograms at different heating rates such as 10, 15 and 20 °C min−1. The contribution of the polar functional groups carried by the synthesized chalcone methacrylamide polymers to some dielectric behavior was examined through the impedance analyzer as a function of frequency. The conductivity values of P-F, P-Cl and P-Br were found 2.00 × 10–9, 2.04 × 10–9 and 1.91 × 10–9 S cm−1, respectively. The SEM images were used to investigate the morphologies of polymers. The surface morphologies and molecular weight distributions of the polymers were imaged by scanning electron microscopy (SEM) and gel permeation chromatography (GPC), respectively. The optical properties of polymers were investigated by UV–Vis and their antimicrobial activities determined by disk diffusion method. The polymers have exhibited good antimicrobial property against Staphylococcus aureus, Klebsiella pneumonia and have exhibited good antifungal property against Candida albicans.
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Demirtaş, E. (2007) Synthesis and improving properties of composites of sodium bentonite and some conductive polymers. MS. Thesis, Gazi University, Ankara, Turkey
Qureshi F, Khuhawar MY, Jahangir TM, Channar AH (2016) Synthesis, characterization and biological studies of new linear thermally stable Schiff base polymers with flexible spacers. Acta Chimica Slovenica 63(1):113–120. https://doi.org/10.17344/acsi.2015.1994
Qureshi F, Khuhawar MY, Jahangir TM (2018) Synthesis and characterization of new photo-responsive ortho and para oriented azomethine polymers. Acta Chimica Slovenica 65(3):718–729. https://doi.org/10.17344/acsi.2018.4419
Qureshi F, Khuhawar MY, Jahangir TM (2019) New fluorescent, thermally stable and film forming polyimines containing naphthyl rings. Acta Chimica Slovenica 66:899–912. https://doi.org/10.17344/acsi.2019.5100
Solomons TWG, Fryhle CB, (2002) Organic Chemistry. Translation Publications, Turkey
Kumar D, Mn K, Akamatsu K, Kusaka E, Harada H, Ito T (2010) Synthesis and biological evaluation of indolylchalcones as antitumor agents. Bioorg & Med Chem Lett 20:3916–3919. https://doi.org/10.1016/j.bmcl.2010.05.016
Ziani N, Lamara K, Sid A, Willem Q, Dassonneville B, Demonceau A (2013) Synthesis of pyrazoline derivatives from the 1,3-dipolar cycloadditions using V. Eur J Chem 4(2):176–179. https://doi.org/10.5155/eurjchem.4.2.176-179.757
Powers DG, Casebier DS, Fokas D, Ryan WJ, Troth JR, Coffen DL (1998) Automated parallel synthesis of chalcone based screening libraries. Tetrahedron 54:4085–4096. https://doi.org/10.1016/S0040-4020(98)00137-9
Boeck P, Falcao CAB, Leal PC, Yunes RA, Filho VC, Santos ECT, Bergman BR (2006) Synthesis of chalcone analogues with increased anti leishmanial activity. Bioorg Med Chem 14:1538–1545. https://doi.org/10.1016/j.bmc.2005.10.005
Hsieh CT, Hsieh TJ, Shazly ME, Chuang DW, Tsai YH, Yen CT, Wu SF, Wu YC, Chang FR (2012) Synthesis of chalcone derivatives as potential anti-diabetic agents. Bioorg Med Chem Lett 22:3912–3915. https://doi.org/10.1016/j.bmcl.2012.04.108
Harborne JB, Williams CA, Harborne JB, Williams CA (2000) Advances in flavonoid research since 1992. Phytochemistry 55:481–504. https://doi.org/10.1016/S0031-9422(00)00235-1
Ghani S, Weaver L, Zidan Z, Ali H, Keevil C, Brown C (2008) Microwave-assisted synthesis and antimicrobial activities of flavonoid derivatives. Bioorg Med Chem Lett 18:518–522. https://doi.org/10.1016/j.bmcl.2007.11.081
Kaya İ, Emdi D, Saçak M (2009) Synthesis, characterization and antimicrobial properties of oligomer and monomer/oligomer-metal complexes of 2-[(pyridine-3-yl-methylene) amino]phenol. J Inorg Organomet Polym Mater 19:286–297. https://doi.org/10.1007/s10904-009-9270-z
Lahtchev KL, Batovska DI, StP P, Ubiyvovk VM, Sibirny AA (2008) Antifungal activity of chalcones: a mechanistic study using various yeast strains. Eur J Med Chem 43:2220–2228. https://doi.org/10.1016/j.ejmech.2007.12.027
Qureshi F, Memon SQ, Khuhawar MY, Jahangir TM (2021) Removal of Co2+, Cu2+ and Au3+ ions from contaminated wastewater by using new fluorescent and antibacterial polymer as sorbent. Polym Bull 78:1505–1533. https://doi.org/10.1007/s00289-020-03170-y
Qureshi F, Khuhawar MY, Jahangir TM, Channar AH (2020) Synthesis and characterization of new thermally stable, antimicrobial and red-light-emitting poly (azomethine-ester) s. Polym Bull. https://doi.org/10.1007/s00289-020-03357-3
Asai T, Hara N, Kobayashi S, Kohshima S, Fujimoto Y (2008) Geranylated flavanones from the secretion on the surface of the immature fruits of Paulownia tomentosa. Phytochemistry 69:1234–1241. https://doi.org/10.1016/j.phytochem.2007.11.011
Beutler JA, Cardellina JH, Gray GN, Prather TR, Shoemaker RH, Boyd MR (1993) Two new cytotoxic chalcones from calythropsis aurea. J Nat Prod 56:1718–1722. https://doi.org/10.1021/np50100a009
Nakamura Y, Watanabe S, Miyake N, Kohno H, Osawa T (2003) Dihydrochalcones: evaluation as novel radical scavenging antioxidants. J Agric Food Chem 51:3309–3312. https://doi.org/10.1021/jf0341060
Go ML, Wu X, Liu X (2005) Chalcones: an update on cytotoxic and chemo preventive properties. Curr Med Chem 12:483–499. https://doi.org/10.2174/0929867053363153
Middleton EJ, Kandaswami C, Theoharides TC (2000) The effect of plant flavonoids on mammalian cells: implications for inflammation, Heart Disease and Cancer. Pharmacol Rev 52:673–751
Alias Y, Awang K, Hadi A (1995) New cyclopeptide alkaloids from zizyphus lotus. J Nat Prod 58:1160–1166. https://doi.org/10.1021/np50122a002
Kim DY, Kim KH, Kim ND, Lee KY, Han CK, Yoon JH, Moon SK, Lee SS, Seong BL (2006) Design and biological evaluation of novel tubulin inhibitors as antimitotic agents using a pharmacophore binding model with tubulin. J Med Chem 49:5664–5670. https://doi.org/10.1021/jm050761i
Lin YM, Zhou Y, Flavin MT, Zhou LM, Nie W, Chen FC (2002) Chalcones and flavonoids as anti-tuberculosis agents. Biorg Med Chem 10:2795–2802. https://doi.org/10.1016/S0968-0896(02)00094-9
Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakiec R, Augustynowicz-Kopec E, Zwolska Z (2007) Synthesis of isomeric, oxathiolone fused chalcones, and comparison of their activity toward various microorganisms and human cancer cells line. Chem Pharm Bull 55:817–820. https://doi.org/10.1248/cpb.55.817
Koca M, Kurt A, Kırılmış C, Aydoğdu Y (2012) Synthesis, Characterization, and thermal degradation of novel poly(2-(5-bromo benzofuran-2-yl)-2-oxoethyl methacrylate). Polym Eng Sci 52:323–330. https://doi.org/10.1002/pen.22085
İzci E (2007) Investigation of dielectric properties of natural and ion-modified forms of gordes region natural clinoptilolite. PhD Thesis, Anadolu University Institute of Science and Technology, Department of Physics, Eskişehir, Turkey
Funiss BS, Hannford AJ, Smith PWG, Tatchell AR (2004) Vogel’s textbook of practical organic chemistry Longman. London 5:1032–1035
Modzelewska A, Pettit C, Achanta G, Davidson NE, Khan HP (2006) Anticancer activities of novel chalcone and bis-chalcone derivatives. Bioorg Med Chem 14:3491–3495. https://doi.org/10.1016/j.bmc.2006.01.003
Biryan F, Pihtili G (2020) Fabrication of a novel acrylate polymer bearing chalcone and amide groups and investigation of its thermal and isoconversional kinetic analysis. J Therm Anal Calorim 139:3857–3870. https://doi.org/10.1007/s10973-019-09243-z
Kolcu F, Kaya İ (2020) A study of the chemical and the enzyme-catalyzed oxidative polymerization of aromatic diamine bearing chlor substituents, pursuant to structural, thermal and photophysical properties. Eur Polym J 133:109767. https://doi.org/10.1016/j.eurpolymj.2020.109767
Doğan F, Kaya İ, Temizkan K (2015) Template-free oxidative synthesis of polyaminonaphthol nanowires. Eur Polymer J 66:397–406. https://doi.org/10.1016/j.eurpolymj.2015.02.026
Flynn JH, Wall LA (1967) Initial kinetic parameters from thermogravimetric rate and conversion data. J Polym Sci, Part C: Polym Lett 5:191–196. https://doi.org/10.1002/pol.1967.110050211
Ozawa T (1986) Applicability of Friedman plot. J Therm Anal 31:547–551. https://doi.org/10.1007/bf01914230
Ozawa T (1970) Kinetic analysis of derivative curves in thermal analysis. J Therm Anal Cal 2:301–324
Delibas A (2008) Synthesis and characterization of (aryl)oxycarbonyl and (aryl)amide side-branched methacrylate polymers. PhD. Thesis, Erciyes University Graduate School of Natural and Applied Sciences, Kayseri, Turkey
Ma S, Hill JO, Heng S (1991) A kinetic analysis of the pyrolysis of some Australian coals by non-isothermal thermogravimetry. J Therm Anal 37:1161–1177. https://doi.org/10.1007/BF01913852
Colladet K, Nicolas M, Goris L, Lutsen L, Vanderzande D (2004) Low band gap polymers for photovoltaic applications. Thin Solid Films 451:7–11. https://doi.org/10.1016/j.tsf.2003.10.085
Temizkan K, Kaya İ (2020) Synthesis of soluble poly(azomethine)s containing thiophene and their fluorescence quantum yields. Polym Bull 77:3287–3303. https://doi.org/10.1007/s00289-019-02911-y
Cazacu M, Marcu M, Vlad A, Rusu GI, Avadanei M (2004) Chelate polymers. VI. New copolymers of some siloxane containing bis (2,4-dihydroxybenzaldehyde-imine) Me2+ with bis-(p-carboxyphenyl) diphenylsilane. J Organometal Chem 689:3005–3011. https://doi.org/10.1016/j.jorganchem.2004.05.051
Qui X, Lu R, Zhou H, Zhang X, Xu T, Liu X, Zhao Y (2007) Synthesis of linear monodisperse vinylene-linked phenothiazine oligomers. Tetrahedron Lett 48:7582–7585. https://doi.org/10.1016/j.tetlet.2007.09.002
Turton R (2005) Physics of Solids (Translation). Aktif Publishing House, Turkey, pp 98–154
Ramya CS, Savitha T, Selvasekharapandian S, Kumar GH (2005) Transport mechanism of cu-ion conducting PVA based solid-polymer electrolyte. Ionics 11:436–441
Çavuş MS (2010) Defect-assisted fractional stochastic heating model of dielectric relaxation. PhD Thesis, Institute of Science, Department of Physics, Adana, Turkey
Çelik T, Coşkun MF (2018) Dielectric and thermal properties of the methacrylate polymer bearing chalcone side group. J Mol Struct 1157:239–246. https://doi.org/10.1016/j.molstruc.2017.12.057
Liu XL, Xu YJ, Go ML (2008) Functionalized chalcones with basic functionalities have antibacterial activity against drug sensitive staphylococcus aureus. Eur J Med Chem 43:1681–1687. https://doi.org/10.1016/j.ejmech.2007.10.007
Boeck P, Leal PC, Yunes RA, Filho VC, Lopez S, Sortino M, Escalante A, Furlan RLE, Zacchino S (2005) Antifungal activity and studies on mode of action of novel xanthoxyline-derived chalcones. Arch Pharm Chem Life Sci 338:87–95. https://doi.org/10.1002/ardp.200400929
Dizman B, Elasri MO, Mathias LJ (2006) Synthesis and characterization of antibacterial and temperature responsive methacrylamide polymers. Macromolecules 39:5738–5746. https://doi.org/10.1021/ma0607620
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Solmaz, A., İlter, Z. & Kaya, İ. Synthesis, characterization, thermal and kinetic properties of chalcone methacrylamide polymers containing halogen group in side chain. Polym. Bull. 79, 5041–5061 (2022). https://doi.org/10.1007/s00289-021-03733-7
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DOI: https://doi.org/10.1007/s00289-021-03733-7