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

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.

Anahtar Kelimeler

• Schiff base
• Sulfo Group
• Thermal properties
• Optical properties
• LOI

Kaynakça

1. [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. [2]. Tüzün, C. 1996. Organic chemistry, 9th press, Palme publisher, pp. 545-547, Ankara, Türkiye.
3. [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. [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. [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. [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. [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. [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. [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. [10]. Bredas, J.L., Street, G.B. 1985. Polarons, bipolarons, and solitons in conducting polymers, Accounts of Chemical Research Journal, 18, 309-315.
11. [11]. van Krevelen, D.W. 1975. Some basic aspects of flame resistance of polymeric materials. Polymer, 16, 615-620.
12. [12]. van Krevelen, D.W. Properties of Polymers, 3rd ed.; Elsevier, New York, 1972.
13. [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.