Yeni Kaliks[4]aren-içeren Polimerik Membranların Hazırlanması, Karakterizasyonu ve Uygulamaları

Yıl 2021, Cilt: 11 Sayı: 2, 533 - 543, 15.12.2021

Mehmet Soner Engin , Serkan Sayın , Seydahmet Çay

https://doi.org/10.31466/kfbd.943146

Öz

Bu çalışmada, 5,17-bis-tert-butil-11,23-dikarboksilik asit-25,27-dihidroksi- 26,28-bis(3-tiyol-1-oksipropan)-kaliks[4]aren (5) bileşiği başarıyla sentezlenmiştir. Sentezlenen bileşiğin yapısı 1HNMR, 13CNMR ve elementel analiz teknikleri kullanılarak aydınlatılmıştır. Elde edilen merkapto grubu bağlı kaliks[4]aren türevi, yeni bir polimer içerikli membran hazırlanması için selüloz triasetat ve 2-nitrofenil oktil eter (o-NPOE) ile birlikte katkı malzemesi olarak kullanılmıştır. Kaliks[4]aren gömülü polimer içeren membranın (KPİM) yapısı ve yüzey morfolojisi, termogravimetrik analiz (TGA) , taramalı elektron mikroskobu (SEM) , Fourier dönüşümlü kızılötesi spektroskopisi (FT-IR) ve elemental analiz teknikleri kullanılarak belirlenmiştir. Ayrıca KPİM in Zn (II), Pb (II), Co(II), Cd (II), Ni (II) ve Cu (II) iyonlarının taşıma etkinliğini değerlendirmek için Donnan diyaliz sistemi kullanılmıştır.

Anahtar Kelimeler

Kaliksaren, Polimer içerikli membran (PİM), Eser metaller, İyon taşınması, Yüzey karakterizasyonu

Destekleyen Kurum

TÜBİTAK

Proje Numarası

215Z570

Fabrication, Characterization, and Application of New Calix[4]arene-embeded Polymer Inclusion Membrane

Öz

In this study, the compound 5,17-bis-tert-butyl-11,23-dicarboxylic acid-25,27-dihydroxy-26,28-bis(3-thiol-1-oxypropane)-calix[4]arene(5) successfully synthesized. The structure of the synthesized compound was characterized using 1HNMR, 13CNMR and elemental analysis techniques. The obtained mercapto group bound calyx[4]arene derivative was used as an additive together with cellulose triacetate and 2-nitrophenyl octyl ether (o-NPOE) for the preparation of a new polymer-containing membrane. The structure and surface morphology of the calyx[4]arene embedded polymeric membrane were determined using thermogravimetric analysis (TGA) , scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR) and elemental analysis techniques. In addition, Donnan dialysis system was used to evaluate the transport efficiency of Zn (II), Pb (II), Co(II), Cd (II), Ni (II) and Cu (II) ions in KPIM.

Anahtar Kelimeler

Calixarene, Polymer inclusion membrane (PIM), Trace metals, Ion transportation, Surface charactrezition

Proje Numarası

215Z570

Kaynakça

• Chester, R., Sohail, M., Ogden, M.I., Mocerino, M., Pretsch, E., De Marco, R. 2014. “A calixarene-based ion-selective electrode for thallium(I) detection”. Analytica Chimica Acta. 851, 78–86.
• Demırkol, D.O., Yildiz, H.B., Sayin, S., Yilmaz, M. 2014. Enzyme immobilization in biosensor constructions: self-assembled monolayers of calixarenes containing thiols. RSC Advances. 4 , 19900-19907.
• Ebdelli, R., Rouis, A., Mlika R., Bonnamour, I., Jaffrezic-Renault, N., Ben Ouada, H., Davenas, J. 2011. Electrochemical impedance detection of Hg2+, Ni2+ and Eu3+ ions by a new azo-calix[4]arene membrane. Journal of Electroanalytical Chemistry. 661,31–38.
• El‐Sayed, M. A.2013. The use of calixarene as ionophores in potentiometric ion‐selective electrodes of naftidrofuryl oxalate using microsized membrane sensors for kinetic study of naftidrofuryl (NFT) degradation. European Journal of Chemistry, 4 (2) ,124‐131.
• Engin M.S., Cay S., Sayin S., Eymur S., Sardohan Koseoglu T. 2017. Preparation of calix [4] arene-embedded polysulphone membranes, and utilisation of its Cr (VI) transport efficiency. Supramolecular Chemistry. 29(6)455-461.
• Engin M.S., Cay S., Sayin S., 2018. Utilization of transport efficacy of novel calix [4] arene-embedded polymer inclusion membrane towards trace metals. Journal of Inclusion Phenomena and Macrocyclic Chemistry. 92(1) 173-179.
• Gokoglan, T.C., Soylemez, S., Kesik, M., Unay, H., Sayin, S., Yildiz, H.B., Cirpan, A., Toppare, L. 2015. A novel architecture based on a conducting polymer and calixarene derivative: its synthesis and biosensor construction. RSC Advances. 5, 35940-35947.
• Ho, W.S.H. ve Sirkar, K.K. 1992 “Dialysis, in Membrane Handbook, Part IV; Van Nostrand Reinhold” New York, 161–215
• Hofman, M. ve Pietrzak, R.2013. Copper ions removal from liquid phase by polyethersulfone (PES) membranes functionalized by introduction of carbonaceous materials. Chemical Engineeing Journal, 215-216, 216-221.
• Gutsche C.D ve Nam K.C. 1988. Calixarenes 22. Synthesis, Properties, and Metal Complexation of Aminocalixarenes. Journal of the American Chemical Society 110(18): 6153-62.
• Kim, J.S., Yu,S.H., Cho,M.H., Shon,O.J., Rim,J.A., Yang,S.H., Lee,J.K., Lee,S.J. 2001. Preparation and Ion-Binding Properties of Calix[4]crown-Containing Polyesters. Bulletin of the Korean Chemical Society. 22, 519.
• Konczyk, J, ve Ciesielski, W. 2021 Calixresorcin[4]arene Mediated Transport of Pb(II) Ions through Polymer Inclusion Membrane. Membranes 11 (4), 285.
• Lamb,J.D. ve Nazarenko, A.Y.1997. Lead(II) ion sorption and transport using polymer inclusion membranes containing tri-octylphosphine oxide. Journal of Membrane Science. 134, 255.
• Levitskaia,T.G., Macdonald,D., Lamb,J., Moyer,B.2000. Prediction of the carrier-mediated cation flux through polymer inclusion membranes via fundamental thermodynamic quantities: complexation study of bis(dodecyloxy)calix[4]arene-crown-6 with alkali metal cations. Physical Chemistry Chemical Physics. 7,1481.
• Li, Z.-T.; Ji, G.-Z.; Zhao, C.-X.; Yuan, S.-D.; Ding, H.; Huang, C.; Du, A.-L.; Wei, M. 1999. Self-assembling calix[4]arene [2]catenanes. Preorganization, conformation, selectivity, and efficiency. Journal of Organic Chemistry. 64, 3572-3584.
• Nagarale, R.K., Gohil, G.S., Shahi,V.K. 2006. Recent developments on ion-exchange membranes and electro-membrane processes. Advances in Colloid and Interface Science, 119, 97-130.
• Nazarenko,A.Y. ve Lamb,J.D. 1997. Selective metal ion sorption and transport using polymer inclusion membranes containing dicyclohexano-18-crown-6. Separation Science and Technology, 32, 2749-2764.
• Sellami, F, Kebiche-Senhadji, O, Marais, S, Colasse, L , Fatyeyeva, K, 2020. Enhanced removal of Cr(VI) by polymer inclusion membrane based on poly (vinylidene fluoride) and Aliquat 336. Separation and Purification Technology, 248, 117038.