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Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups

Yıl 2024, , 101 - 106, 29.12.2024
https://doi.org/10.18466/cbayarfbe.1529884

Öz

Aromatic mono- or diamine compounds containing sulfonic groups are extensively utilized in the production of textiles, dyes, and polymers. Schiff base compounds are synthesized through the condensation reactions of these types of compounds with aromatic aldehydes or ketones. Due to their multifunctional nature, these Schiff base compounds serve as precursors in the synthesis of poly(ester)s, poly(ether)s, poly(urethane)s, and poly(azomethine)s. The Schiff base compounds were 2,5-bis((E)-(2-hydroxybenzylidene)amino)benzene sulfonic acid (SCH1) and 4,4'-bis((E)-(2-hydroxybenzylidene)amino)-[1,1'-biphenyl]-2,2'-disulfonic acid (SCH2). The yields of SCH1 and SCH2 were calculated to be 85% and 80%, respectively. Structural confirmation was achieved using FT-IR, UV-Vis, 1H NMR and 13C NMR measurements. Further characterization through fluorescence spectroscopy (PL), thermogravimetric analysis (TGA) and cyclic voltammetry (CV) revealed high thermal stability of the compounds, attributed to the phenyl groups in their structures. TGA measurements indicated the initial decomposition temperatures for SCH1 and SCH2 at 298°C and 347 °C, respectively, with the residual masses of 34.64% and 41.24% at 1000 °C.

Kaynakça

  • [1]. Park, S., Mathur, V.K., Planalp, R.P. 1998. Synthesis, solubilities and oxygen absorption properties of new Cobalt (II) Schiff base complexes, Polyhedron, 17 (2-3): 325-330.
  • [2]. Tüzün, C. 1996. Organic chemistry, 9th press, Palme publisher, pp. 545-547, Ankara, Türkiye.
  • [3]. Zhang, T., Bai, R., Shen, J., Wang, O., Wang, P., Yuan, J., Fan, X. 2018. Laccase-catalyzed polymerization of diaminobenzene sulfonic acid for pH-responsive color-changing and conductive wool fabrics, Textile Research Journal; 88 (19): 2258-2266.
  • [4]. Kaya, İ., Akyüz, B., Kolcu, F., Söyüt, H. 2022. Facile one-pot synthesis of water-soluble conjugated polymers derived from 7-amino-4-hydroxy-2-naphthalenesulfonic acid: Synthesis and photoluminesence properties, Reactive and Functional Polymers; 175: Article Nu.105281.
  • [5]. Kaya, İ., Kolcu, F., Satılmış, S., Yazıcıoğlu, Z. 2018. Synthesis and characterization of fluorescent polyphenols anchored Schiff bases via oxidative polycondensation, Materials Science-Poland; 36 (4), 584-596.
  • [6]. Yang, J.C., Jablonsky, M.J., Mays, J. 2002. NMR and FT-IR studies of sulfonated styrene-based homopolymers and copolymers, Polymer, 43, 5125-5132.
  • [7]. Burns, M., Wagenknecht, U., Kretzschmar, B., Focke, W.W. 2008. Effect of hydrated fillers and red phosphorus on the limiting oxygen index of poly(ethylene-co-vinyl acetate)-poly(vinyl butyral) and low density polyethylene-poly(ethylene-co-vinyl alcohol) blends, Journal of Vinyl and Additive Technology, 14 (3), 113-119.
  • [8]. Kolcu F, Kaya İ. 2024. Oligomerization of dibrominated aminophenol on the basis of the chemical and HRP-catalyzed oxidative processes: Characterization and photoluminescence properties, Dyes and Pigments, 227, Article Nu.112185.
  • [9]. Liu, W., Lee, S., Yang, S., Bian, S., Lia, L., Samuelson, L.A., Kumar, J., Tripathy, S.K. 2001. Biologically derived photoactive macromolecular azodyes. Journal of Macromolecular Science - Pure and Applied Chemistry, 38 A (12) 1355-1370.
  • [10]. Bredas, J.L., Street, G.B. 1985. Polarons, bipolarons, and solitons in conducting polymers, Accounts of Chemical Research Journal, 18, 309-315.
  • [11]. van Krevelen, D.W. 1975. Some basic aspects of flame resistance of polymeric materials. Polymer, 16, 615-620.
  • [12]. van Krevelen, D.W. Properties of Polymers, 3rd ed.; Elsevier, New York, 1972.
  • [13]. Arora, S., Mestry, S., Naik, D., Mhaske, S. 2020. o-phenylenediamine-derived phosphorus-based cyclic flame retardant for epoxy and polyurethane systems. Polymer Bulletin, 77, 3185-3205.
Yıl 2024, , 101 - 106, 29.12.2024
https://doi.org/10.18466/cbayarfbe.1529884

Öz

Kaynakça

  • [1]. Park, S., Mathur, V.K., Planalp, R.P. 1998. Synthesis, solubilities and oxygen absorption properties of new Cobalt (II) Schiff base complexes, Polyhedron, 17 (2-3): 325-330.
  • [2]. Tüzün, C. 1996. Organic chemistry, 9th press, Palme publisher, pp. 545-547, Ankara, Türkiye.
  • [3]. Zhang, T., Bai, R., Shen, J., Wang, O., Wang, P., Yuan, J., Fan, X. 2018. Laccase-catalyzed polymerization of diaminobenzene sulfonic acid for pH-responsive color-changing and conductive wool fabrics, Textile Research Journal; 88 (19): 2258-2266.
  • [4]. Kaya, İ., Akyüz, B., Kolcu, F., Söyüt, H. 2022. Facile one-pot synthesis of water-soluble conjugated polymers derived from 7-amino-4-hydroxy-2-naphthalenesulfonic acid: Synthesis and photoluminesence properties, Reactive and Functional Polymers; 175: Article Nu.105281.
  • [5]. Kaya, İ., Kolcu, F., Satılmış, S., Yazıcıoğlu, Z. 2018. Synthesis and characterization of fluorescent polyphenols anchored Schiff bases via oxidative polycondensation, Materials Science-Poland; 36 (4), 584-596.
  • [6]. Yang, J.C., Jablonsky, M.J., Mays, J. 2002. NMR and FT-IR studies of sulfonated styrene-based homopolymers and copolymers, Polymer, 43, 5125-5132.
  • [7]. Burns, M., Wagenknecht, U., Kretzschmar, B., Focke, W.W. 2008. Effect of hydrated fillers and red phosphorus on the limiting oxygen index of poly(ethylene-co-vinyl acetate)-poly(vinyl butyral) and low density polyethylene-poly(ethylene-co-vinyl alcohol) blends, Journal of Vinyl and Additive Technology, 14 (3), 113-119.
  • [8]. Kolcu F, Kaya İ. 2024. Oligomerization of dibrominated aminophenol on the basis of the chemical and HRP-catalyzed oxidative processes: Characterization and photoluminescence properties, Dyes and Pigments, 227, Article Nu.112185.
  • [9]. Liu, W., Lee, S., Yang, S., Bian, S., Lia, L., Samuelson, L.A., Kumar, J., Tripathy, S.K. 2001. Biologically derived photoactive macromolecular azodyes. Journal of Macromolecular Science - Pure and Applied Chemistry, 38 A (12) 1355-1370.
  • [10]. Bredas, J.L., Street, G.B. 1985. Polarons, bipolarons, and solitons in conducting polymers, Accounts of Chemical Research Journal, 18, 309-315.
  • [11]. van Krevelen, D.W. 1975. Some basic aspects of flame resistance of polymeric materials. Polymer, 16, 615-620.
  • [12]. van Krevelen, D.W. Properties of Polymers, 3rd ed.; Elsevier, New York, 1972.
  • [13]. Arora, S., Mestry, S., Naik, D., Mhaske, S. 2020. o-phenylenediamine-derived phosphorus-based cyclic flame retardant for epoxy and polyurethane systems. Polymer Bulletin, 77, 3185-3205.
Toplam 13 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Malzeme Karekterizasyonu
Bölüm Makaleler
Yazarlar

İsmet Kaya 0000-0002-9813-2962

Feyza Kolcu 0000-0002-2004-8859

Sude Süel 0009-0002-9110-283X

Yayımlanma Tarihi 29 Aralık 2024
Gönderilme Tarihi 8 Ağustos 2024
Kabul Tarihi 11 Kasım 2024
Yayımlandığı Sayı Yıl 2024

Kaynak Göster

APA Kaya, İ., Kolcu, F., & Süel, S. (2024). Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, 20(4), 101-106. https://doi.org/10.18466/cbayarfbe.1529884
AMA Kaya İ, Kolcu F, Süel S. Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups. CBUJOS. Aralık 2024;20(4):101-106. doi:10.18466/cbayarfbe.1529884
Chicago Kaya, İsmet, Feyza Kolcu, ve Sude Süel. “Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 20, sy. 4 (Aralık 2024): 101-6. https://doi.org/10.18466/cbayarfbe.1529884.
EndNote Kaya İ, Kolcu F, Süel S (01 Aralık 2024) Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 20 4 101–106.
IEEE İ. Kaya, F. Kolcu, ve S. Süel, “Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups”, CBUJOS, c. 20, sy. 4, ss. 101–106, 2024, doi: 10.18466/cbayarfbe.1529884.
ISNAD Kaya, İsmet vd. “Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 20/4 (Aralık 2024), 101-106. https://doi.org/10.18466/cbayarfbe.1529884.
JAMA Kaya İ, Kolcu F, Süel S. Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups. CBUJOS. 2024;20:101–106.
MLA Kaya, İsmet vd. “Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, c. 20, sy. 4, 2024, ss. 101-6, doi:10.18466/cbayarfbe.1529884.
Vancouver Kaya İ, Kolcu F, Süel S. Synthesis and Characterization of Schiff Base Compounds Containing Mono and Disulfonic Groups. CBUJOS. 2024;20(4):101-6.