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Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties

Yıl 2022, Cilt: 18 Sayı: 2, 185 - 191, 30.06.2021
https://doi.org/10.18466/cbayarfbe.1070592

Öz

In this study, a poly(azomethine) compound (SBP) containing sulfur and oxygen bridge was obtained from 4,4'-[thiobis(4,1-phenyleneoxy)]dibenzaldehyde (DBA) and 4,4'diamino-2,2'-biphenyl sulfonic acid from condensation reaction. Structural, optical, electrochemical and morphological analyzes of the obtained polymeric material were performed. Structural characterizations were performed from 1H-NMR and FT-IR spectra. Optical properties were determined in the UV-Vis spectrum and the optical band gap was calculated as 3.63 eV. Electrochemical properties were investigated by cyclic voltammetry (CV) and HOMO-LUMO and electrochemical band gap values were calculated. In addition, with the help of Gel Permeation Chromatography (GPC), the number average molecular mass was found to be 5050 Da. By thermogravimetric analysis (TGA), it was found that the thermal decomposition of SBP occurred in four steps and the maximum mass loss was 391 °C. The surface analysis of the obtained polymeric material was investigated with scanning electron microscope (SEM) and it was determined that the surface was rough.

Kaynakça

  • [1] Kamaci, UD, Kamaci, M, Peksel, A. 2017. Thermally Stable Schiff Base and its Metal Complexes: Molecular Docking and Protein Binding Studies. Journal of Fluorescence; 27: 805–817.
  • [2] Mighani, H. 2020. Schiff Base polymers: synthesis and characterization. Journal of Polymer Research; 27 (6): 168.
  • [3] Puchtler, H, Meloan, SN. 1981. On Schiff’s bases and aldehyde-fuchsin: A review from H. Schiff to R.D. Lillie. Histochemistry; 72: 321–332.
  • [4] Nitschke, P, Jarząbek, B, Vasylieva, M, Honisz, D, Małecki, JG, Musioł, M, Janeczek, H, Chaber, P. 2021. Influence of chemical structure on thermal, optical and electrochemical properties of conjugated azomethines, Synthetic Metals; 273: 116689.
  • [5] Grigoras, M, Catanescu, CO. 2004. Imine oligomers and polymers. Journal of Macromolecular Science: Part C: Polymer Reviews; 44: 131–173.
  • [6] Kaya, İ, Ayten, B, Şenol D. 2018. Syntheses of poly(phenoxy-imine)s anchored with carboxyl group: Characterization and photovoltaic studies. Optical Materials; 78: 421–431.
  • [7] Karacan Yeldir, E, Erdener, D, Kaya, İ. 2022. Synthesis and characterization of a pyrene-based Schiff base and its oligomer: Investigation of fluorescent Cr3+ probe. Reactive and Functional Polymer; 170: 105097.
  • [8] Yılmaz Baran, N, Saçak, M. 2018. Preparation of highly thermally stable and conductive Schiff base polymer: Molecular weight monitoring and investigation of antimicrobial properties, Journal of Molecular Structure; 1163: 22–32.
  • [9] Avci, A, Kamaci, M, Kaya, I, Yildirim, M. 2015. Synthesis of Novel crosslinked Poly(azomethine-urethane)s: Photophysical and thermal properties. Materials Chemistry and Physics; 163: 301–310.
  • [10] Guo, Z, Sun, P, Zhang, X, Lin, J, Shi, T, Liu, S, Sun, A, Li, Z. 2018. Amorphous Porous Organic Polymers Based on Schiff-Base Chemistry for Highly Efficient Iodine Capture. Chemistry - An Asian Journal; 13: 2046–2053.
  • [11] Iwan, A. 2015. An overview of LC polyazomethines with aliphatic-aromatic moieties: Thermal, optical, electrical and photovoltaic properties. Renewable and Sustainable Energy Reviews; 52: 65–79.
  • [12] Jarzabek, B, Weszka, J, Hajduk, B, Jurusik, J, Domanski, M, Cisowski, J. 2011. A study of optical properties and annealing effect on the absorption edge of pristine- and iodine-doped polyazomethine thin films. Synthetic Metals; 161: 969–975.
  • [13] Marin, L, Perju, E, Damaceanu, MD. 2011. Designing thermotropic liquid crystalline polyazomethines based on fluorene and/or oxadiazole chromophores. European Polymer Journal; 47: 1284–1299.
  • [14] Iwan, A, Boharewicz, B, Tazbir, I, Filapek, M. 2015. Enhanced power conversion efficiency in bulk heterojunction solar cell based on new polyazomethine with vinylene moieties and [6,6]-phenyl C61 butyric acid methyl ester by adding 10-camphorsulfonic acid. Electrochimica Acta, 159: 81–92.
  • [15] Iwan, A, Sek, D. 2008. Processible polyazomethines and polyketanils: From aerospace to light-emitting diodes and other advanced applications. Progress in Polymer Science; 33: 289–345.
  • [16] Bhadra, J, Madi, NK, Al-Thani, NJ, Al-Maadeed, M.A. 2014. Polyaniline/polyvinyl alcohol blends: Effect of sulfonic acid dopants on microstructural, optical, thermal and electrical properties. Synthetic Metals; 191: 126–134.
  • [17] Jung, SH, Lee, TW, Kim, YC, Suh, DH, Cho, HN.2003. Synthesis and characterization of fluorene-based poly(azomethines). Optical Materials; 21: 169–173.
  • [18] Wolska, J, Stawicka, K, Walkowiak-Kulikowska, J. 2021. Sulfonic-acid-functionalized polymers based on fluorinated methylstyrenes and styrene as promising heterogeneous catalysts for esterification. Materials Chemistry and Physics; 273: 125132.
  • [19] Hassan, MM. 2021. Energy-efficient dyeing of wool fabrics with sulfonic acid derivatives of aniline by oxidation polymerization, Sustainable Materials and Technologies; 29: e00290.
  • [20] Elibal, F, Gumustekin, S, Ozkazanc, H, Ozkazanc, E. 2021. Poly(N-methylpyrrole) with high antibacterial activity synthesized via interfacial polymerization method. Journal of Molecular Structure; 1242: 130712.
  • [21] Thangarasu, R, Dharmalingam, K, Ramasundaram, S, Elangovan, T, Balasundaram, ON, Pathak, TK. 2021. The role of polymeric surfactants on morphology and volatile organic compounds sensing efficiency of tennis bat like vanadium pentoxide nanorod. Journal of Environmental Chemical Engineering; 9: 105683.
  • [22] Çulhaoğlu, S, Kaya, I. 2015. Synthesis , Characterization , Thermal Stability and Conductivity of New Schiff Base Polymer Containing Sulfur and Oxygen Bridges. Polymer(Korea); 39: 225–234.
  • [23] Kaya, I, Kolcu, F. 2018. Polymerization of Chrysoidine with chemical and enzymatic oxidative preference: Synthesis, characterization, and spectroscopic study. Polymers for Advanced Technologies; 29: 2515–2528.
  • [24] Olgun, U, Dikmen, Z, Çetin, H, Arıcan, F, Gülfen, M. 2022. Synthesis, optical dye properties and band gap energies of silver hydroxy-aryl thiazolo[5,4-d]thiazole complexes. Journal of Molecular Structure; 1250: 131816.
  • [25] Kaya, I, Karacan Yeldir, E. 2021. Comparative study on oxidative and enzyme catalyzed oxidative polymerization of aminophenol compound containing dihalogen. Journal of Polymer Research; 28: 1–16.
Yıl 2022, Cilt: 18 Sayı: 2, 185 - 191, 30.06.2021
https://doi.org/10.18466/cbayarfbe.1070592

Öz

Kaynakça

  • [1] Kamaci, UD, Kamaci, M, Peksel, A. 2017. Thermally Stable Schiff Base and its Metal Complexes: Molecular Docking and Protein Binding Studies. Journal of Fluorescence; 27: 805–817.
  • [2] Mighani, H. 2020. Schiff Base polymers: synthesis and characterization. Journal of Polymer Research; 27 (6): 168.
  • [3] Puchtler, H, Meloan, SN. 1981. On Schiff’s bases and aldehyde-fuchsin: A review from H. Schiff to R.D. Lillie. Histochemistry; 72: 321–332.
  • [4] Nitschke, P, Jarząbek, B, Vasylieva, M, Honisz, D, Małecki, JG, Musioł, M, Janeczek, H, Chaber, P. 2021. Influence of chemical structure on thermal, optical and electrochemical properties of conjugated azomethines, Synthetic Metals; 273: 116689.
  • [5] Grigoras, M, Catanescu, CO. 2004. Imine oligomers and polymers. Journal of Macromolecular Science: Part C: Polymer Reviews; 44: 131–173.
  • [6] Kaya, İ, Ayten, B, Şenol D. 2018. Syntheses of poly(phenoxy-imine)s anchored with carboxyl group: Characterization and photovoltaic studies. Optical Materials; 78: 421–431.
  • [7] Karacan Yeldir, E, Erdener, D, Kaya, İ. 2022. Synthesis and characterization of a pyrene-based Schiff base and its oligomer: Investigation of fluorescent Cr3+ probe. Reactive and Functional Polymer; 170: 105097.
  • [8] Yılmaz Baran, N, Saçak, M. 2018. Preparation of highly thermally stable and conductive Schiff base polymer: Molecular weight monitoring and investigation of antimicrobial properties, Journal of Molecular Structure; 1163: 22–32.
  • [9] Avci, A, Kamaci, M, Kaya, I, Yildirim, M. 2015. Synthesis of Novel crosslinked Poly(azomethine-urethane)s: Photophysical and thermal properties. Materials Chemistry and Physics; 163: 301–310.
  • [10] Guo, Z, Sun, P, Zhang, X, Lin, J, Shi, T, Liu, S, Sun, A, Li, Z. 2018. Amorphous Porous Organic Polymers Based on Schiff-Base Chemistry for Highly Efficient Iodine Capture. Chemistry - An Asian Journal; 13: 2046–2053.
  • [11] Iwan, A. 2015. An overview of LC polyazomethines with aliphatic-aromatic moieties: Thermal, optical, electrical and photovoltaic properties. Renewable and Sustainable Energy Reviews; 52: 65–79.
  • [12] Jarzabek, B, Weszka, J, Hajduk, B, Jurusik, J, Domanski, M, Cisowski, J. 2011. A study of optical properties and annealing effect on the absorption edge of pristine- and iodine-doped polyazomethine thin films. Synthetic Metals; 161: 969–975.
  • [13] Marin, L, Perju, E, Damaceanu, MD. 2011. Designing thermotropic liquid crystalline polyazomethines based on fluorene and/or oxadiazole chromophores. European Polymer Journal; 47: 1284–1299.
  • [14] Iwan, A, Boharewicz, B, Tazbir, I, Filapek, M. 2015. Enhanced power conversion efficiency in bulk heterojunction solar cell based on new polyazomethine with vinylene moieties and [6,6]-phenyl C61 butyric acid methyl ester by adding 10-camphorsulfonic acid. Electrochimica Acta, 159: 81–92.
  • [15] Iwan, A, Sek, D. 2008. Processible polyazomethines and polyketanils: From aerospace to light-emitting diodes and other advanced applications. Progress in Polymer Science; 33: 289–345.
  • [16] Bhadra, J, Madi, NK, Al-Thani, NJ, Al-Maadeed, M.A. 2014. Polyaniline/polyvinyl alcohol blends: Effect of sulfonic acid dopants on microstructural, optical, thermal and electrical properties. Synthetic Metals; 191: 126–134.
  • [17] Jung, SH, Lee, TW, Kim, YC, Suh, DH, Cho, HN.2003. Synthesis and characterization of fluorene-based poly(azomethines). Optical Materials; 21: 169–173.
  • [18] Wolska, J, Stawicka, K, Walkowiak-Kulikowska, J. 2021. Sulfonic-acid-functionalized polymers based on fluorinated methylstyrenes and styrene as promising heterogeneous catalysts for esterification. Materials Chemistry and Physics; 273: 125132.
  • [19] Hassan, MM. 2021. Energy-efficient dyeing of wool fabrics with sulfonic acid derivatives of aniline by oxidation polymerization, Sustainable Materials and Technologies; 29: e00290.
  • [20] Elibal, F, Gumustekin, S, Ozkazanc, H, Ozkazanc, E. 2021. Poly(N-methylpyrrole) with high antibacterial activity synthesized via interfacial polymerization method. Journal of Molecular Structure; 1242: 130712.
  • [21] Thangarasu, R, Dharmalingam, K, Ramasundaram, S, Elangovan, T, Balasundaram, ON, Pathak, TK. 2021. The role of polymeric surfactants on morphology and volatile organic compounds sensing efficiency of tennis bat like vanadium pentoxide nanorod. Journal of Environmental Chemical Engineering; 9: 105683.
  • [22] Çulhaoğlu, S, Kaya, I. 2015. Synthesis , Characterization , Thermal Stability and Conductivity of New Schiff Base Polymer Containing Sulfur and Oxygen Bridges. Polymer(Korea); 39: 225–234.
  • [23] Kaya, I, Kolcu, F. 2018. Polymerization of Chrysoidine with chemical and enzymatic oxidative preference: Synthesis, characterization, and spectroscopic study. Polymers for Advanced Technologies; 29: 2515–2528.
  • [24] Olgun, U, Dikmen, Z, Çetin, H, Arıcan, F, Gülfen, M. 2022. Synthesis, optical dye properties and band gap energies of silver hydroxy-aryl thiazolo[5,4-d]thiazole complexes. Journal of Molecular Structure; 1250: 131816.
  • [25] Kaya, I, Karacan Yeldir, E. 2021. Comparative study on oxidative and enzyme catalyzed oxidative polymerization of aminophenol compound containing dihalogen. Journal of Polymer Research; 28: 1–16.
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Elif Karacan Yeldir 0000-0001-8638-1198

Yayımlanma Tarihi 30 Haziran 2021
Yayımlandığı Sayı Yıl 2022 Cilt: 18 Sayı: 2

Kaynak Göster

APA Karacan Yeldir, E. (2021). Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties. Celal Bayar University Journal of Science, 18(2), 185-191. https://doi.org/10.18466/cbayarfbe.1070592
AMA Karacan Yeldir E. Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties. CBUJOS. Haziran 2021;18(2):185-191. doi:10.18466/cbayarfbe.1070592
Chicago Karacan Yeldir, Elif. “Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties”. Celal Bayar University Journal of Science 18, sy. 2 (Haziran 2021): 185-91. https://doi.org/10.18466/cbayarfbe.1070592.
EndNote Karacan Yeldir E (01 Haziran 2021) Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties. Celal Bayar University Journal of Science 18 2 185–191.
IEEE E. Karacan Yeldir, “Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties”, CBUJOS, c. 18, sy. 2, ss. 185–191, 2021, doi: 10.18466/cbayarfbe.1070592.
ISNAD Karacan Yeldir, Elif. “Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties”. Celal Bayar University Journal of Science 18/2 (Haziran 2021), 185-191. https://doi.org/10.18466/cbayarfbe.1070592.
JAMA Karacan Yeldir E. Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties. CBUJOS. 2021;18:185–191.
MLA Karacan Yeldir, Elif. “Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties”. Celal Bayar University Journal of Science, c. 18, sy. 2, 2021, ss. 185-91, doi:10.18466/cbayarfbe.1070592.
Vancouver Karacan Yeldir E. Synthesis of Poly(azomethine) Containing Sulfonic Acid Unit Oxygen and Sulphur Bridged: Investigation of Its Thermal, Optical and Electrochemical Properties. CBUJOS. 2021;18(2):185-91.