Synthesis, Characterization of Chalcone Containing Methacrylate Polymers: Investigation of Fluorescence, Thermal and Dielectric Properties

Yıl 2016, Cilt: 16 Sayı: 2, 230 - 238, 30.04.2016

Mehmet Fatih Coşkun , Adem Şentürk Demet Coşkun

Öz

In this study, the (1‐benzofurane‐2‐yl)‐3‐oxo‐prop‐1‐en‐1‐yl]‐2‐methoxyphenyl 2‐methyl acrylate monomer were synthesized from the acylation reaction of this compound with methacryloyl chloride that commercially purchased. Free radicalic or atom transfer radical polymerization methods were used for preparation of copolymers. FT‐IR, 1H and 13C‐NMR techniques were used for structure characterization of polymers. The thermal behaviors of polymers were relatively investigated by DSC and TGA, and the results were compared with each other. The dielectric behaviors of polymers were investigated as a function of temperature and frequency. The results obtained were associated with their the structures. The spectroscopic properties of the polymers were investigated by UV‐Vis and fluorescence spectroscopies. Effects of the solvent polarity on emission measurement were investigated with fluorescence spectroscopy. Under cover of dimerization property of chalcone, the chalcone ended polymer was photodimerizatied.

Anahtar Kelimeler

Thermal properties, Dielectric Properties, Chalcone, Photodimerization, Fluorescence

Kalkon İçerikli Metakrilat Polimerlerinin Sentezi, Karakterizasyonu, Termal, Dielektrik ve Floresans Özelliklerinin İncelenmesi

Öz

Bu çalışmada, (1‐benzofuran‐2‐il)’ in vanilin ile reaksiyonundan (1‐benzofuran‐2‐il)‐3‐(4‐ hidroksi‐3‐metoksifenil)prop‐2‐en‐1‐on sentezlendi. Sentezlenen bu bileşik ile ticari olarak hazır alınan metakriloilklorür ile açilleme reaksiyonundan (1‐benzofuran‐2‐il)‐3‐okso‐prop‐1‐ en‐1‐il]‐2‐metoksifenil 2‐metilakrilat monomeri sentezlendi. Homopolimer ve kopolimerlerin hazırlanmasında serbest radikalik polimerizasyon ve atom transfer radikal polimerizasyon metodları kullanıldı. Yapı karakterizasyonunda ağırlıklı olarak FT‐IR, 1H ve 13C‐NMR teknikleri kullanıldı. Polimerlerin termal davranışları karşılaştırmalı olarak DSC ve TGA ile ölçüldü ve sonuçlar birbirleriyle karşılaştırıldı. Ortalama molekül ağırlıkları ve polidispersiteleri GPC ile ölçüldü. Sıcaklık ve frekansın bir fonksiyonu olarak polimerlerin dielektrik davranışları incelendi ve yapılarıyla ilişkilendirildi. Polimerlerin spektroskopik özellikleri UV‐Vis ve floresans spektroskopileriyle araştırıldı. Floresans spektroskopisiyle emisyon ölçümleri üzerine çözücü polarlığının etkisi araştırıldı. Kalkonun dimerleşme özelliğinden yararlanılarak kalkon uçlu polimer fotodimerleştirildi.

Anahtar Kelimeler

Termal özellik, Dielektrik özellik, Kalkon, Fotodimerizasyon, Floresans

Kaynakça

• Jeong, J.W., Kwon, Y., Han, Y.S., Park, L.S., 2005. Electroluminescent property and photolithographic process of photosensitive random copolymers. Molecular Crystals and Liquid Crystals, 443, 59‐68.
• Zhang, L.Z., Li, Y., Liang, Z.X., Yu, Q.S., Cai, Z.G., 1999. New crosslinked polymer systems with high and stable optical nonlinearity. Reactive and Functional Polymer, 40, 255‐262.
• Mizoguchi, K., Hasegawa, E., 1996. Photoactive polymers applied to advanced microelectronic devices. Polymers for Advanced Technologies, 7, 471‐477.
• Song, D.M., Jung, K.H., Moon, J.H., Shin, D.M., 2002. Photochemistry of chalcone and the application of chalcone‐derivatives in photoalignment layer of liquid crystal display. Optical Materials, 21, 667‐671.
• Allen, N.S., Khan, L., Edge, M., Billings, M., Vercs, J., 1998. Studies on UV and thermally radical induced cross‐linked polymer networks as charge‐transport layers in electrophotographic coating applications. Journal of Photochemistry and Photobiology A: Chemistry, 116, 235‐244.
• Trenor, S.R., Shultz, A.R., Love, B.J., Long, T.E., 2004. Coumarins in polymers: from light harvesting to photo‐cross‐linkable tissue scaffolds. Chemical Reviews, 104, 3059‐3077.
• Tamilvanan, M., Pandurangan, A., Reddy, B.S.R., Subramanian, K., 2007. Synthesis, characterization and properties of photoresponsive polymers comprising photocrosslinkable pendant chalcone moieties. Polymer International, 56, 104‐ 111.
• Santhi, R., Babu, K.V., Penlidis, A., Nanjundan, S., 2006. Studies on copolymers of 3‐ methacryloyloxystyryl‐4′‐methylphenyl ketone and methyl methacrylate. Reactive & Functional Polymers, 66, 1215‐1226.
• Park, H.H., Choi, Y., Park, D.J., Cho, S.Y., Yun, Y.S., Jin, H.J., 2013. Enhanced dielectric properties of electrospun titanium dioxide/polyvinylidene fluoride nanofibrous composites. Fibers and Polymers, 14(9), 1521‐1525.
• Coskun, D., Ahmedzade, M., 2008. 3‐(Substituted aryl)‐1‐(benzofuran‐2‐yl)‐2‐propenones, Part 1: synthesis and characterization of some novel chalcones. Synthetic Communications, 38, 3613‐3622.
• Bezgin, F., 2011. Synthesis of polymers containing coumarin spectroscopic and dielectric properties. PhD Thesis, University of Firat Graduate School of Sciences, Elazig. Singh, K.P., Gupta, P.N., 1998. Study of dielectric relaxation in polymer electrolytes. European Polymer Journal, 34, 1023‐1029.
• Rao, V., Ashokan, P.V., Shridhar, M.H., 2000. Studies of dielectric relaxation and ac conductivity in cellulose acetate hydrogen Polymersphthalate–poly (methyl methacrylate) blends. Materials Sciences and Engineering: A, 281, 213‐220.
• Selvam, P., Babu, K.V., Penlidis, A., Nanjundan, S., 2005. Studies on photocrosslinkable copolymers of 4‐methacryloyloxyphenyl‐3 ',4 '‐dimethoxystyryl ketone and methyl methacrylate. European Polymer Journal, 41, 831‐841.
• Balaji, R., Grande, D., Nanjundan, S., 2004. Photoresponsive polymers having pendant chlorocinnamoyl moieties: synthesis, reactivity ratios and photochemical properties. Polymer, 45, 1089‐1099.
• Unal, M., 2008. Some Benzimidazole Derivative Fluorimetric Investigation of Properties. Ph Thesis, University of Selcuk Graduate School of Sciences, Konya.