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Yeni okzadiazol ve triazol bazlı kaliksaren türevlerinin sentezi ve ekstraksiyon özellikleri

Yıl 2022, Cilt: 24 Sayı: 1, 222 - 231, 05.01.2022

Ali Osman Karatavuk

https://doi.org/10.25092/baunfbed.898019

Öz

Bu çalışmada, okzadiazol ve triazol türevi taşıyan iki yeni kaliksaren türevi bileşik sentezlendi. Elde edilen nihai ürünlerin yapıları 1H-NMR, 13C-NMR, FT-IR ve HR-MS analizleri ile aydınlatıldı. Bu bileşikler ile sıvı-sıvı ekstraksiyonu yapılarak sulu çözeltideki metil oranjın uzaklaştırılmasında etkinlikleri değerlendirildi. Ayrıca ekstraksiyon yüzdesi üzerine H+ iyonu konsantrasyonu ve NaCl konsantrasyonunun etkisi incelendi. Elde edilen sonuçlar ekstraksiyon yüzdesinin H+ iyonu konsantrasyonuna bağlı olduğunu gösterdi. Triazol türevi 5 için sulu ortamdan metil oranjın uzaklaştırılma yüzdesi % 53.3 olarak bulundu.

Anahtar Kelimeler

Kaliksaren okzadiazol triazol ekstraksiyon.

Kaynakça

  • Molad, A., Goldberg, I. and Vigalok, A., Tubular Conjugated Polymer for Chemosensory Applications, Journal of American Chemical Society, 134, 17, 7290-7292, (2012).
  • Troisi, F., Pierro, T., Gaeta, C. and Neri, P., The p-Bromodienone Route to Nucleophilic Functionalization of Calixarene Exo Rim, Organic Letters, 11, 3, 697-700 (2009).
  • Cao, X., Luo, L., Zhang, F., Miao, F., Tian, D. and Li, H., Synthesis of a deep cavity calix[4]arene by fourfold Sonogashira cross-coupling reaction and selective fluorescent recognition toward p-nitrophenol, Tetrahedron Letters, 55, 12, 2029-2032, (2014).
  • Xu, Z., Lü, Z.S. and Chen, L., Enhanced etherification of calix[4]arenes by microwave irradiation, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 88, 1-2, 77-83, (2017).
  • Drigo, N.A., Gorbunov, A.N., Gorbunov, D.N., Talanova, M.Y., Kardasheva, Y.S., Kovalev, V.V., Maximov, A.L. and Vatsouro, I.M., Synthesis of polyfunctional phosphorus-containing calixarenes in cycloaddition reactions of azides to alkynes, Chemistry of Heterocyclic Compounds, 52, 12, 1042-1053, (2016).
  • Shalev, O. and Biali, S.E., C–Me Bond Formation at All Methylene Bridges of the Calix[4]arene Scaffold, Organic Letters, 20, 11, 3390-3393, (2018).
  • Poms, D., Itzhak, N., Kuno, L. and Biali, S.E. Calixradialenes: Calixarene Derivatives with Exocyclic Double Bonds, Journal of Organic Chemistry. 79, 2, 538-545, (2014).
  • Tlustý, M., Slavík, P., Dvořáková, H., Eigner, V. and Lhoták, P., Synthesis and study of calix[4]arenes bearing azo moieties at the meta position, Tetrahedron, 73, 9, 1230-1237, (2017).
  • Stejskal, F., Eigner, V., Dvořáková, H., Cuřínová, P. and Lhoták, P., Direct C–H azidation of calix[4]arene as a novel method to access meta substituted derivatives, Tetrahedron Letters, 56, 39, 5357-5361, (2015).
  • Toma, L., Legnani, L., Compostella, F., Giuliani, M., Faroldi, F., Casnati, A. and Sansone, F., Molecular Architecture and Symmetry Properties of 1,3-Alternate Calix[4]arenes with Orientable Groups at the Para Position of the Phenolic Rings, Journal of Organic Chemistry. 81, 20, 9718-9727, (2016).
  • Slavík, P., Eigner, V. and Lhoták, P., A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation, Tetrahedron, 72, 41, 6348-6355, (2016).
  • Yang, Y., Cao, X., Purkiss, D.W., Cannon, J.F. and Bartsch, R.A., Di-ionizable calix[4]arene-1,3-crown-4 ligands in 1,3-alternate, cone, and partial-cone conformations: synthesis and metal ion extractions, Tetrahedron, 68, 10, 2233-2244, (2012).
  • Augusto, A.S., Miranda, A.S., Ascenso, J.R., Miranda, M.Q., Félix, V., Brancatelli, G., Hickey, N., Geremia, S. and Marcos, P.M., Anion Recognition by Partial Cone Dihomooxacalix[4]arene‐Based Receptors Bearing Urea Groups: Remarkable Affinity for Benzoate Ion, European Journal of Organic Chemistry, 2018, 41, 5657-5667, (2018).
  • Feng, J., Liu, K., Li, Y. and Yang, M., A novel calixarene‐containing hyperbranched aliphatic polyester incorporated with pendant europium complexes, Polymers for Advanced Technologies, 20, 6, 514-518, (2009).
  • Nakahara, Y., Furuno, Y., Iwamoto, H., Yajima, S. and Kimura, K. A tetraester derivative of fluorescent calix[4]arene bearing a proton-ionizable moiety for highly sensitive extraction-fluorometric determination of sodium ion, Supramolecular Chemistry, 30, 8, 697-705, (2018).
  • Uysal Akkus, G., Ala E. and Korcan, S.E., Selective extraction of toxic heavy metals and biological activity studies using pyrimidylthioamide functionalised calix[4]arene, Supramolecular Chemistry, 27, 7-8, 522-526, (2015).
  • Sayin, S., Yildiz, H.B. and Eymur, S., Synthesis of Various Calix[4]arene Derivatives with Mercaptoalkyl Chains and Their Application in Removing Cr(VI) from Aqueous Solution, Polycyclic Aromatic Compounds, 28, 2, 120-130, (2018).
  • Sayin, S., Ozcan F. and Yilmaz, M., Two novel calixarene functionalized iron oxide magnetite nanoparticles as a platform for magnetic separation in the liquid–liquid/solid–liquid extraction of oxyanions, Materials Science and Engineering C, 33, 2433-2439, (2013).
  • Ahuja, B.B. and Vigalok, A., Fluorescent Calixarene Scaffolds for NO Detection in Protic Media, Angewandte Chemie International Edition, 58, 9, 2774-2778, (2019).
  • Sahin, O. and Yilmaz, M., Synthesis and fluorescence sensing properties of a new naphthalimide derivative of calix[4]arene, Tetrahedron Letters, 53, 18, 2319-2324 (2012).
  • Güngör, Ö., Efficient removal of carcinogenic azo dyes by novel pyrazine-2-carboxylate substituted calix[4, 8]arene derivatives, Supramolecular Chemistry, 31, 12, 776–783, (2019).
  • Kamboh, M.A., Akoz, E., Memon S. and Yilmaz, M., Synthesis of Amino-Substituted p-tert-Butylcalix[4]arene for the Removal of Chicago Sky Blue and Tropaeolin 000 Azo Dyes from Aqueous Environment, Water, Air, & Soil Pollution, 224, 1424, (2013).
  • Güngör, Ö., Liquid phase extraction of azo dyes by novel calixarenes bearing phthalonitrile and diiminoisoindoline groups, Separation Science and Technology, 53, 6, 896-902, (2018).
  • Akceylan, E., Bahadir M. and Yılmaz, M., Removal efficiency of a calix[4]arene-based polymer for water-soluble carcinogenic direct azo dyes and aromatic amines, Journal of Hazardous Materials, 162, 960-966, (2009).
  • Kamboh, M.A., Solangi, I.B., Sherazi S.T.H. and Memon, S., Synthesis and application of p-tert-butylcalix[8]arene immobilized material for the removal of azo dyes, Desalination, 268, 83–89, (2011).
  • Kamboh, M.A., Solangi, I.B., Sherazi S.T.H. and Memon, S., Synthesis and application of p-tert-butylcalix[8]arene immobilized material for the removal of azo dyes, Journal of Hazardous Materials, 186, 651–658, (2011).
  • Kamboh, M.A., Solangi, I.B., Sherazi S.T.H. and Memon, S., Synthesis and application of calix[4]arene based resin for the removal of azo dyes, Journal of Hazardous Materials, 172, 234–239, (2009).
  • Thakkar, S.S., Thakor, P., Doshi, H. and Ray, A., 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities, Bioorganic & Medicinal Chemistry, 25, 15, 4064-4075, (2017).
  • Khanam, R., Kumar, R., Hejazi, I.I., Shahabuddin, S., Meena, R., Rajamani, P., Yadav, N., Bhat, A.I. and Athar, F., New N‐benzhydrylpiperazine/1,3,4‐oxadiazoles conjugates inhibit the proliferation, migration, and induce apoptosis in HeLa cancer cells via oxidative stress–mediated mitochondrial pathway, Journal of Cellular Biochemistry, 120, 2, 1651-1666, (2019).
  • Özil, M., Balaydın, H.T. and Şentürk, M., Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties, Bioorganic Chemistry, 86, 705-713, (2019).
  • Boström, J., Hogner, A., Llinàs, A., Wellner, E. and Plowright, A.T., Oxadiazoles in Medicinal Chemistry, Journal of Medicinal Chemistry, 55, 5 1817-1830, (2012).
  • Galstyan, A.S., Ghochikyan, T.V., Frangyan, V.R., Tamazyan, R.A. and Ayvazyan, A.G., Synthesis of Novel Derivatives of 1,2,4‐Triazoles, ChemistrySelect, 3, 35, 9981-9985 (2018).
  • Jasiak, K. and Kudelko, A., Oxidative cyclization of N-aroylhydrazones to 2-(2-arylethenyl)-1,3,4-oxadiazoles using DDQ as an efficient oxidant, Tetrahedron Letters, 56, 43, 5878-5881, (2015).
  • Zarudnitskii, E.V., Pervak, I.I., Merkulov, A.S., Yurchenko, A.A. and Tolmachev, A.A., Trimethylsilyl-1,3,4-oxadiazoles—new useful synthons for the synthesis of various 2,5-disubstituted-1,3,4-oxadiazoles, Tetrahedron, 64, 45, 10431-10442, (2008).
  • Chen, Z., Liu, Y., Zhang, C. and Bai, F., Synthesis and properties of photoluminescent copolymer containing 1,3,4‐oxadiazole and carbazole rings, Journal of Applied Polymer Science, 92, 5, 2777-2783, (2004).
  • Xie, D.-H., Wang, X.-J., Sun, C. and Han, J., Calix[4]arene based 1,3,4-oxadiazole as a fluorescent chemosensor for copper(II) ion detection, Tetrahedron Letters, 57, 51, 5834-5836, (2016).
  • Jia, T.-J., Cao, W., Zheng, X.-J. and Jin, L.-P., A turn-on chemosensor based on naphthol–triazole for Al(III) and its application in bioimaging, Tetrahedron Letters, 54, 26, 3471-3474, (2013).
  • Shalaeva, Y.V., Morozova, J.E., Mironova, D.A., Kazakova, E.K., Kadirov, M.T., Nizameev I.R. and Konovalov, A.I., Amidoamine calix[4]resorcinarene-based oligomers and polymers as efficient sorbents of azo dyes from water, Supramolecular Chemistry, 27, 9, 595–605, (2015).
  • Memon, S., Bhatti A.A. and Bhatti, A.A., Calix[4]arene Resin, An Efficient Adsorbent for Azo Dyes, Polycyclic Aromatic Compounds, 39, 3, 238-247, (2019).
  • Shengquan, Y., Hui, W., Chaohua Z. and Fu, H., Separation of carcinogenic aromatic amines in the food colourants plant wastewater treatment, Desalination, 222, 294–301, (2008).
  • Hosseini, S., Khan, M.A., Malekbala, M.R., Cheah W. and Choong, T.S.Y., Carbon coated monolith, a mesoporous material for the removal of methyl orange from aqueous phase: Adsorption and desorption studies, Chemical Engineering Journal, 171, 1124– 1131, (2011).
  • Gutsche, C.D., Iqbal, M. and Stewart, D., Calixarenes. 19. Syntheses procedures for p-tert-butylcalix[4]arene, Journal of Organic Chemistry, 51, 5, 742-745, (1986).
  • Li, Z.-T., Ji, G.-Z., Zhao, C.-X., Yuan, S.-D., Ding, H., Huang, C., Du, A.-L. and Wei, M., Self-Assembling Calix[4]arene [2]Catenanes. Preorganization, Conformation, Selectivity, and Efficiency, Journal of Organic Chemistry, 64, 10, 3572-3584, (1999).

Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties

Yıl 2022, Cilt: 24 Sayı: 1, 222 - 231, 05.01.2022

Ali Osman Karatavuk

https://doi.org/10.25092/baunfbed.898019

Öz

Two new calixarene derivative compounds bearing oxadiazole and triazole groups were synthesized. The final products were illuminated by using 1H-NMR, 13C-NMR, FT-IR and HR-MS. The extraction efficiency of these compounds was investigated in the removal of methyl orange. In addition, the effect of H+ ion concentration in extraction studies conducted in different pH ranges and the effect of NaCl concentration on the percentage of extraction was examined. The results obtained showed that the percentage of extraction was highly dependent on the H+ ion concentration. It was found that the percentage of methyl orange removal was 53.3% for triazole derivatives 5.

Anahtar Kelimeler

calixarene oxadiazole triazole extraction

Kaynakça

  • Molad, A., Goldberg, I. and Vigalok, A., Tubular Conjugated Polymer for Chemosensory Applications, Journal of American Chemical Society, 134, 17, 7290-7292, (2012).
  • Troisi, F., Pierro, T., Gaeta, C. and Neri, P., The p-Bromodienone Route to Nucleophilic Functionalization of Calixarene Exo Rim, Organic Letters, 11, 3, 697-700 (2009).
  • Cao, X., Luo, L., Zhang, F., Miao, F., Tian, D. and Li, H., Synthesis of a deep cavity calix[4]arene by fourfold Sonogashira cross-coupling reaction and selective fluorescent recognition toward p-nitrophenol, Tetrahedron Letters, 55, 12, 2029-2032, (2014).
  • Xu, Z., Lü, Z.S. and Chen, L., Enhanced etherification of calix[4]arenes by microwave irradiation, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 88, 1-2, 77-83, (2017).
  • Drigo, N.A., Gorbunov, A.N., Gorbunov, D.N., Talanova, M.Y., Kardasheva, Y.S., Kovalev, V.V., Maximov, A.L. and Vatsouro, I.M., Synthesis of polyfunctional phosphorus-containing calixarenes in cycloaddition reactions of azides to alkynes, Chemistry of Heterocyclic Compounds, 52, 12, 1042-1053, (2016).
  • Shalev, O. and Biali, S.E., C–Me Bond Formation at All Methylene Bridges of the Calix[4]arene Scaffold, Organic Letters, 20, 11, 3390-3393, (2018).
  • Poms, D., Itzhak, N., Kuno, L. and Biali, S.E. Calixradialenes: Calixarene Derivatives with Exocyclic Double Bonds, Journal of Organic Chemistry. 79, 2, 538-545, (2014).
  • Tlustý, M., Slavík, P., Dvořáková, H., Eigner, V. and Lhoták, P., Synthesis and study of calix[4]arenes bearing azo moieties at the meta position, Tetrahedron, 73, 9, 1230-1237, (2017).
  • Stejskal, F., Eigner, V., Dvořáková, H., Cuřínová, P. and Lhoták, P., Direct C–H azidation of calix[4]arene as a novel method to access meta substituted derivatives, Tetrahedron Letters, 56, 39, 5357-5361, (2015).
  • Toma, L., Legnani, L., Compostella, F., Giuliani, M., Faroldi, F., Casnati, A. and Sansone, F., Molecular Architecture and Symmetry Properties of 1,3-Alternate Calix[4]arenes with Orientable Groups at the Para Position of the Phenolic Rings, Journal of Organic Chemistry. 81, 20, 9718-9727, (2016).
  • Slavík, P., Eigner, V. and Lhoták, P., A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation, Tetrahedron, 72, 41, 6348-6355, (2016).
  • Yang, Y., Cao, X., Purkiss, D.W., Cannon, J.F. and Bartsch, R.A., Di-ionizable calix[4]arene-1,3-crown-4 ligands in 1,3-alternate, cone, and partial-cone conformations: synthesis and metal ion extractions, Tetrahedron, 68, 10, 2233-2244, (2012).
  • Augusto, A.S., Miranda, A.S., Ascenso, J.R., Miranda, M.Q., Félix, V., Brancatelli, G., Hickey, N., Geremia, S. and Marcos, P.M., Anion Recognition by Partial Cone Dihomooxacalix[4]arene‐Based Receptors Bearing Urea Groups: Remarkable Affinity for Benzoate Ion, European Journal of Organic Chemistry, 2018, 41, 5657-5667, (2018).
  • Feng, J., Liu, K., Li, Y. and Yang, M., A novel calixarene‐containing hyperbranched aliphatic polyester incorporated with pendant europium complexes, Polymers for Advanced Technologies, 20, 6, 514-518, (2009).
  • Nakahara, Y., Furuno, Y., Iwamoto, H., Yajima, S. and Kimura, K. A tetraester derivative of fluorescent calix[4]arene bearing a proton-ionizable moiety for highly sensitive extraction-fluorometric determination of sodium ion, Supramolecular Chemistry, 30, 8, 697-705, (2018).
  • Uysal Akkus, G., Ala E. and Korcan, S.E., Selective extraction of toxic heavy metals and biological activity studies using pyrimidylthioamide functionalised calix[4]arene, Supramolecular Chemistry, 27, 7-8, 522-526, (2015).
  • Sayin, S., Yildiz, H.B. and Eymur, S., Synthesis of Various Calix[4]arene Derivatives with Mercaptoalkyl Chains and Their Application in Removing Cr(VI) from Aqueous Solution, Polycyclic Aromatic Compounds, 28, 2, 120-130, (2018).
  • Sayin, S., Ozcan F. and Yilmaz, M., Two novel calixarene functionalized iron oxide magnetite nanoparticles as a platform for magnetic separation in the liquid–liquid/solid–liquid extraction of oxyanions, Materials Science and Engineering C, 33, 2433-2439, (2013).
  • Ahuja, B.B. and Vigalok, A., Fluorescent Calixarene Scaffolds for NO Detection in Protic Media, Angewandte Chemie International Edition, 58, 9, 2774-2778, (2019).
  • Sahin, O. and Yilmaz, M., Synthesis and fluorescence sensing properties of a new naphthalimide derivative of calix[4]arene, Tetrahedron Letters, 53, 18, 2319-2324 (2012).
  • Güngör, Ö., Efficient removal of carcinogenic azo dyes by novel pyrazine-2-carboxylate substituted calix[4, 8]arene derivatives, Supramolecular Chemistry, 31, 12, 776–783, (2019).
  • Kamboh, M.A., Akoz, E., Memon S. and Yilmaz, M., Synthesis of Amino-Substituted p-tert-Butylcalix[4]arene for the Removal of Chicago Sky Blue and Tropaeolin 000 Azo Dyes from Aqueous Environment, Water, Air, & Soil Pollution, 224, 1424, (2013).
  • Güngör, Ö., Liquid phase extraction of azo dyes by novel calixarenes bearing phthalonitrile and diiminoisoindoline groups, Separation Science and Technology, 53, 6, 896-902, (2018).
  • Akceylan, E., Bahadir M. and Yılmaz, M., Removal efficiency of a calix[4]arene-based polymer for water-soluble carcinogenic direct azo dyes and aromatic amines, Journal of Hazardous Materials, 162, 960-966, (2009).
  • Kamboh, M.A., Solangi, I.B., Sherazi S.T.H. and Memon, S., Synthesis and application of p-tert-butylcalix[8]arene immobilized material for the removal of azo dyes, Desalination, 268, 83–89, (2011).
  • Kamboh, M.A., Solangi, I.B., Sherazi S.T.H. and Memon, S., Synthesis and application of p-tert-butylcalix[8]arene immobilized material for the removal of azo dyes, Journal of Hazardous Materials, 186, 651–658, (2011).
  • Kamboh, M.A., Solangi, I.B., Sherazi S.T.H. and Memon, S., Synthesis and application of calix[4]arene based resin for the removal of azo dyes, Journal of Hazardous Materials, 172, 234–239, (2009).
  • Thakkar, S.S., Thakor, P., Doshi, H. and Ray, A., 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities, Bioorganic & Medicinal Chemistry, 25, 15, 4064-4075, (2017).
  • Khanam, R., Kumar, R., Hejazi, I.I., Shahabuddin, S., Meena, R., Rajamani, P., Yadav, N., Bhat, A.I. and Athar, F., New N‐benzhydrylpiperazine/1,3,4‐oxadiazoles conjugates inhibit the proliferation, migration, and induce apoptosis in HeLa cancer cells via oxidative stress–mediated mitochondrial pathway, Journal of Cellular Biochemistry, 120, 2, 1651-1666, (2019).
  • Özil, M., Balaydın, H.T. and Şentürk, M., Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties, Bioorganic Chemistry, 86, 705-713, (2019).
  • Boström, J., Hogner, A., Llinàs, A., Wellner, E. and Plowright, A.T., Oxadiazoles in Medicinal Chemistry, Journal of Medicinal Chemistry, 55, 5 1817-1830, (2012).
  • Galstyan, A.S., Ghochikyan, T.V., Frangyan, V.R., Tamazyan, R.A. and Ayvazyan, A.G., Synthesis of Novel Derivatives of 1,2,4‐Triazoles, ChemistrySelect, 3, 35, 9981-9985 (2018).
  • Jasiak, K. and Kudelko, A., Oxidative cyclization of N-aroylhydrazones to 2-(2-arylethenyl)-1,3,4-oxadiazoles using DDQ as an efficient oxidant, Tetrahedron Letters, 56, 43, 5878-5881, (2015).
  • Zarudnitskii, E.V., Pervak, I.I., Merkulov, A.S., Yurchenko, A.A. and Tolmachev, A.A., Trimethylsilyl-1,3,4-oxadiazoles—new useful synthons for the synthesis of various 2,5-disubstituted-1,3,4-oxadiazoles, Tetrahedron, 64, 45, 10431-10442, (2008).
  • Chen, Z., Liu, Y., Zhang, C. and Bai, F., Synthesis and properties of photoluminescent copolymer containing 1,3,4‐oxadiazole and carbazole rings, Journal of Applied Polymer Science, 92, 5, 2777-2783, (2004).
  • Xie, D.-H., Wang, X.-J., Sun, C. and Han, J., Calix[4]arene based 1,3,4-oxadiazole as a fluorescent chemosensor for copper(II) ion detection, Tetrahedron Letters, 57, 51, 5834-5836, (2016).
  • Jia, T.-J., Cao, W., Zheng, X.-J. and Jin, L.-P., A turn-on chemosensor based on naphthol–triazole for Al(III) and its application in bioimaging, Tetrahedron Letters, 54, 26, 3471-3474, (2013).
  • Shalaeva, Y.V., Morozova, J.E., Mironova, D.A., Kazakova, E.K., Kadirov, M.T., Nizameev I.R. and Konovalov, A.I., Amidoamine calix[4]resorcinarene-based oligomers and polymers as efficient sorbents of azo dyes from water, Supramolecular Chemistry, 27, 9, 595–605, (2015).
  • Memon, S., Bhatti A.A. and Bhatti, A.A., Calix[4]arene Resin, An Efficient Adsorbent for Azo Dyes, Polycyclic Aromatic Compounds, 39, 3, 238-247, (2019).
  • Shengquan, Y., Hui, W., Chaohua Z. and Fu, H., Separation of carcinogenic aromatic amines in the food colourants plant wastewater treatment, Desalination, 222, 294–301, (2008).
  • Hosseini, S., Khan, M.A., Malekbala, M.R., Cheah W. and Choong, T.S.Y., Carbon coated monolith, a mesoporous material for the removal of methyl orange from aqueous phase: Adsorption and desorption studies, Chemical Engineering Journal, 171, 1124– 1131, (2011).
  • Gutsche, C.D., Iqbal, M. and Stewart, D., Calixarenes. 19. Syntheses procedures for p-tert-butylcalix[4]arene, Journal of Organic Chemistry, 51, 5, 742-745, (1986).
  • Li, Z.-T., Ji, G.-Z., Zhao, C.-X., Yuan, S.-D., Ding, H., Huang, C., Du, A.-L. and Wei, M., Self-Assembling Calix[4]arene [2]Catenanes. Preorganization, Conformation, Selectivity, and Efficiency, Journal of Organic Chemistry, 64, 10, 3572-3584, (1999).
Toplam 43 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Araştırma Makalesi
Yazarlar

Ali Osman Karatavuk 0000-0001-6616-4065

Yayımlanma Tarihi 5 Ocak 2022
Gönderilme Tarihi 16 Mart 2021
Yayımlandığı Sayı Yıl 2022 Cilt: 24 Sayı: 1

Kaynak Göster

APA Karatavuk, A. O. (2022). Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 24(1), 222-231. https://doi.org/10.25092/baunfbed.898019
AMA Karatavuk AO. Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties. BAUN Fen. Bil. Enst. Dergisi. Ocak 2022;24(1):222-231. doi:10.25092/baunfbed.898019
Chicago Karatavuk, Ali Osman. “Novel Oxadiazole- and Triazole-Based Calixarene Derivatives: Synthesis and Extraction Properties”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 24, sy. 1 (Ocak 2022): 222-31. https://doi.org/10.25092/baunfbed.898019.
EndNote Karatavuk AO (01 Ocak 2022) Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 24 1 222–231.
IEEE A. O. Karatavuk, “Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties”, BAUN Fen. Bil. Enst. Dergisi, c. 24, sy. 1, ss. 222–231, 2022, doi: 10.25092/baunfbed.898019.
ISNAD Karatavuk, Ali Osman. “Novel Oxadiazole- and Triazole-Based Calixarene Derivatives: Synthesis and Extraction Properties”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 24/1 (Ocak 2022), 222-231. https://doi.org/10.25092/baunfbed.898019.
JAMA Karatavuk AO. Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties. BAUN Fen. Bil. Enst. Dergisi. 2022;24:222–231.
MLA Karatavuk, Ali Osman. “Novel Oxadiazole- and Triazole-Based Calixarene Derivatives: Synthesis and Extraction Properties”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 24, sy. 1, 2022, ss. 222-31, doi:10.25092/baunfbed.898019.
Vancouver Karatavuk AO. Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties. BAUN Fen. Bil. Enst. Dergisi. 2022;24(1):222-31.