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Synthesis and Characterization of Schiff Bases and Cu(II) and Ni(II) Complexes of Polyhedral Oligomeric Silsesquioxane (POSS) Compounds

Yıl 2022, Cilt: 12 Sayı: 3, 1665 - 1676, 01.09.2022
https://doi.org/10.21597/jist.1102515

Öz

In this study, two different polyhedral oligomeric silsesquioxane (POSS) were
synthesized using 3-aminopropyltriethoxysilane (APTES) and N-(2-aminoethyl)-3-
aminopropyltrimethoxysilane (AEPTMS). POSS Schiff bases were synthesized as a result of the condensation reaction of POSS compounds with salicylaldehyde and 5-bromosalicylaldehyde. The
structures of POSS and its ligand derivatives were by spectroscopic (Elemental analysis (C, H, N), 1HNMR, 29Si-NMR, FT-IR) methods. Cu(II) and Ni(II) metal complexes of Schiff Bases were also synthesized. The structures of the isolated POSS Schiff base metal complexes were tried to be clarified with FT-IR, Magnetic susceptibility balance and ICP-OES. The results showed that metal ions bind to Schiff bases via phenolic oxygen and azomethine nitrogen.

Kaynakça

  • Allan JR, Gardner AR, Mccloy B, Smith WE, 1992. Structural and thermal studies of the chlorocomplexes of cobalt, nickel and copper with 2,6- diaminopyridine and an assessment of their suitability as antistatic additives for polyethylene. Thermochimica Acta, 208: 125-131.
  • Arshadi M, Ghiaci M, 2011. Highly efficient solvent free oxidation of ethylbenzene using some recyclable catalysts: The role of linker in competency of manganese nanocatalysts. Applied Catalysis A: General, 399: 75-86.
  • Berber N, Arslan M, 2020. Preparation and characterization of some Schiff base compounds. Adıyaman University Journal of Science, 10(1):179-188.
  • Durak D, Delikanlı A, Demetgül C, Kani İ, Serin S, 2013. Crystal structure of an unsymmetrical Schiff base, immobilization of its cobalt and manganese complexes on a silica support, and catalytic studies. Transition Metal Chemistry, 38:199–206.
  • Gravel MC, Zhang C, Dinderman M, Laine RM, 1999. Octa(3-chloroammoniumpropyl) octasilsesquioxane. Applied Organometallic Chemistry 13: 329–336.
  • Grigoropoulou G, Stathi P, Karakassides MA, Louloudi M, Deligiannakis Y, 2008. Functionalized SiO2 with N-, S-containing ligands for Pb(II) and Cd(II) adsorption, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 320(1–3): 25-35.
  • Gündüz T, 1994. Koordinasyon Kimyası, Ankara Üniversitesi Fen Fakültesi Kimya Bölümü, Ankara.
  • Harrison PG, 1997. Silicate cages:precursors to new materials. Journal of Organometallic Chemsitry, 542:141.
  • Hill A, Fink MJ, 2008. Advances in Organometallic Chemistry. Academic Press, Volume 57, pp 50-52, USA.
  • İspir E. 2014. Synthesis and characterization of silica-supported Schiff base ligands and their metal complexes: applications as catalysts for the oxidation of alkanes. Phosphorus, Sulfur, and Silicon, 189:1644–1655.
  • Lichtenhan JD, Schwab JJ, Feher FJ, Soulivong D, 1999. U.S. Patent 5942638.
  • Mehta A, Tembe G, Białek M, Parikh P, Mehta G, 2012. Synthesis and catalytic studies of Ti-anchored disilanol isobutyl-POSS/alkylaluminum system. Journal of Molecular Catalysis A: Chemical, 361-362: 17-28.
  • Scovill JP, 1982. 2-Acetylpyridine thiosemicarbazones 3. Complexes with transition metals as antimalarial and antileukemic agents, Journal of Medicinal Chemistry, 25(10): 1261-1264.
  • Serin S, 1980. 1,3-Difenil-2-tio-4,5-bis(hidroksiimino)-1,2,4,5-tetrahidroimidazol eldesi, geometrik izomerleri, geçiş metalleri ile kompleks formasyonları. K.T.Ü. Fen Bilimleri Enstitüsü, Doktora Tezi, Trabzon (Basılmış).
  • Tarafder MTH, Mial LMA, 1986. Novel peroxo complexes of zirconium containing organicligants, Inorganic Chemistry, 25(13): 2265-2268.
  • Timur M, Demetgül C, 2017. Synthesis and metal ıon uptake studies of silica gel -ımmobilized schiff base derivatives and catalytic behaviors of their Cu(II) complexes. Iranian Journal of Chemistry and Chemical Engineering, 36(4): 111-122.
  • Tingaut P, Hauert R, Zimmermann T, 2011. Highly efficient and straightforward functionalization of cellulose films with thiol-ene click chemistry. Journal of Materials Chemistry, 2011(21): 16066–16076.
  • Tümer M, Köksal H, Serin S. Patat Ş, 1997. Synthesis and characterization of some cobalt(II), nickel(II) and zinc(II) complexes with Schiff bases derived from the reaction of 4-hydroxisalicylaldehyde and o-vanillin with 3,5-di(tert-butyl)-4-hydroxyaniline. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 27(1): 59-68.
  • Wheeler PA, Fu BX, Lichtenhan JD, Weitao J, Mathias LJ, 2006. Incorporation of metallic POSS, POSS copolymers, and new functionalized poss compounds into commercial dental resins. Journal of Applied Polymer Science, 102: 2856–2862.
  • Xie K, Yanli Z, Si C, 2010. Synthesis and characterization of reactive polyhedral oligomeric silsesquioxanes (R-POSS) containing multi-N-methylol groups. Journal of Organometallic Chemistry. 695(5): 687-691.

Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları ve Cu(II) ve Ni(II) Komplekslerinin Sentezi ve Karakterizasyonu

Yıl 2022, Cilt: 12 Sayı: 3, 1665 - 1676, 01.09.2022
https://doi.org/10.21597/jist.1102515

Öz

Bu çalışmada, 3-aminopropiltrietoksisilan (APTES) ve N-(2-aminoetil)-3-aminopropiltrimetoksisilan (AEPTMS) kullanılarak iki farklı polihedral oligomerik silseskioksan (POSS) sentezlenmiştir. Elde edilen bu POSS bileşikleri, salisilaldehit ve 5-bromosalisilaldehit ile kondenzasyon tepkimesi sonucu POSS Schiff bazları sentezlenmiştir. POSS ve ligand özelliğindeki türevlerinin yapıları spektroskopik (Elementel analiz (C, H, N), 1H-NMR, 29Si NMR, FT-IR) yöntemlerle aydınlatılmıştır. Schiff Bazlarının Cu(II) ve Ni(II) metal kompleksleri sentezlenmiştir. İzole edilen POSS Schiff bazı metal komplekslerinin yapıları FT-IR, Magnetik duyarlılık terazisi ve ICP-OES ile aydınlatılmaya çalışılmıştır. Sonuçlar, metal iyonlarının Schiff bazlarına fenolik oksijen ve azometin azotu üzerinden bağlandığını göstermiştir.

Kaynakça

  • Allan JR, Gardner AR, Mccloy B, Smith WE, 1992. Structural and thermal studies of the chlorocomplexes of cobalt, nickel and copper with 2,6- diaminopyridine and an assessment of their suitability as antistatic additives for polyethylene. Thermochimica Acta, 208: 125-131.
  • Arshadi M, Ghiaci M, 2011. Highly efficient solvent free oxidation of ethylbenzene using some recyclable catalysts: The role of linker in competency of manganese nanocatalysts. Applied Catalysis A: General, 399: 75-86.
  • Berber N, Arslan M, 2020. Preparation and characterization of some Schiff base compounds. Adıyaman University Journal of Science, 10(1):179-188.
  • Durak D, Delikanlı A, Demetgül C, Kani İ, Serin S, 2013. Crystal structure of an unsymmetrical Schiff base, immobilization of its cobalt and manganese complexes on a silica support, and catalytic studies. Transition Metal Chemistry, 38:199–206.
  • Gravel MC, Zhang C, Dinderman M, Laine RM, 1999. Octa(3-chloroammoniumpropyl) octasilsesquioxane. Applied Organometallic Chemistry 13: 329–336.
  • Grigoropoulou G, Stathi P, Karakassides MA, Louloudi M, Deligiannakis Y, 2008. Functionalized SiO2 with N-, S-containing ligands for Pb(II) and Cd(II) adsorption, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 320(1–3): 25-35.
  • Gündüz T, 1994. Koordinasyon Kimyası, Ankara Üniversitesi Fen Fakültesi Kimya Bölümü, Ankara.
  • Harrison PG, 1997. Silicate cages:precursors to new materials. Journal of Organometallic Chemsitry, 542:141.
  • Hill A, Fink MJ, 2008. Advances in Organometallic Chemistry. Academic Press, Volume 57, pp 50-52, USA.
  • İspir E. 2014. Synthesis and characterization of silica-supported Schiff base ligands and their metal complexes: applications as catalysts for the oxidation of alkanes. Phosphorus, Sulfur, and Silicon, 189:1644–1655.
  • Lichtenhan JD, Schwab JJ, Feher FJ, Soulivong D, 1999. U.S. Patent 5942638.
  • Mehta A, Tembe G, Białek M, Parikh P, Mehta G, 2012. Synthesis and catalytic studies of Ti-anchored disilanol isobutyl-POSS/alkylaluminum system. Journal of Molecular Catalysis A: Chemical, 361-362: 17-28.
  • Scovill JP, 1982. 2-Acetylpyridine thiosemicarbazones 3. Complexes with transition metals as antimalarial and antileukemic agents, Journal of Medicinal Chemistry, 25(10): 1261-1264.
  • Serin S, 1980. 1,3-Difenil-2-tio-4,5-bis(hidroksiimino)-1,2,4,5-tetrahidroimidazol eldesi, geometrik izomerleri, geçiş metalleri ile kompleks formasyonları. K.T.Ü. Fen Bilimleri Enstitüsü, Doktora Tezi, Trabzon (Basılmış).
  • Tarafder MTH, Mial LMA, 1986. Novel peroxo complexes of zirconium containing organicligants, Inorganic Chemistry, 25(13): 2265-2268.
  • Timur M, Demetgül C, 2017. Synthesis and metal ıon uptake studies of silica gel -ımmobilized schiff base derivatives and catalytic behaviors of their Cu(II) complexes. Iranian Journal of Chemistry and Chemical Engineering, 36(4): 111-122.
  • Tingaut P, Hauert R, Zimmermann T, 2011. Highly efficient and straightforward functionalization of cellulose films with thiol-ene click chemistry. Journal of Materials Chemistry, 2011(21): 16066–16076.
  • Tümer M, Köksal H, Serin S. Patat Ş, 1997. Synthesis and characterization of some cobalt(II), nickel(II) and zinc(II) complexes with Schiff bases derived from the reaction of 4-hydroxisalicylaldehyde and o-vanillin with 3,5-di(tert-butyl)-4-hydroxyaniline. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 27(1): 59-68.
  • Wheeler PA, Fu BX, Lichtenhan JD, Weitao J, Mathias LJ, 2006. Incorporation of metallic POSS, POSS copolymers, and new functionalized poss compounds into commercial dental resins. Journal of Applied Polymer Science, 102: 2856–2862.
  • Xie K, Yanli Z, Si C, 2010. Synthesis and characterization of reactive polyhedral oligomeric silsesquioxanes (R-POSS) containing multi-N-methylol groups. Journal of Organometallic Chemistry. 695(5): 687-691.
Toplam 20 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Bestami Atik 0000-0003-2346-955X

Cahit Demetgül 0000-0003-1559-7279

Erken Görünüm Tarihi 26 Ağustos 2022
Yayımlanma Tarihi 1 Eylül 2022
Gönderilme Tarihi 13 Nisan 2022
Kabul Tarihi 26 Nisan 2022
Yayımlandığı Sayı Yıl 2022 Cilt: 12 Sayı: 3

Kaynak Göster

APA Atik, B., & Demetgül, C. (2022). Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları ve Cu(II) ve Ni(II) Komplekslerinin Sentezi ve Karakterizasyonu. Journal of the Institute of Science and Technology, 12(3), 1665-1676. https://doi.org/10.21597/jist.1102515
AMA Atik B, Demetgül C. Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları ve Cu(II) ve Ni(II) Komplekslerinin Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. Eylül 2022;12(3):1665-1676. doi:10.21597/jist.1102515
Chicago Atik, Bestami, ve Cahit Demetgül. “Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları Ve Cu(II) Ve Ni(II) Komplekslerinin Sentezi Ve Karakterizasyonu”. Journal of the Institute of Science and Technology 12, sy. 3 (Eylül 2022): 1665-76. https://doi.org/10.21597/jist.1102515.
EndNote Atik B, Demetgül C (01 Eylül 2022) Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları ve Cu(II) ve Ni(II) Komplekslerinin Sentezi ve Karakterizasyonu. Journal of the Institute of Science and Technology 12 3 1665–1676.
IEEE B. Atik ve C. Demetgül, “Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları ve Cu(II) ve Ni(II) Komplekslerinin Sentezi ve Karakterizasyonu”, Iğdır Üniv. Fen Bil Enst. Der., c. 12, sy. 3, ss. 1665–1676, 2022, doi: 10.21597/jist.1102515.
ISNAD Atik, Bestami - Demetgül, Cahit. “Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları Ve Cu(II) Ve Ni(II) Komplekslerinin Sentezi Ve Karakterizasyonu”. Journal of the Institute of Science and Technology 12/3 (Eylül 2022), 1665-1676. https://doi.org/10.21597/jist.1102515.
JAMA Atik B, Demetgül C. Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları ve Cu(II) ve Ni(II) Komplekslerinin Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. 2022;12:1665–1676.
MLA Atik, Bestami ve Cahit Demetgül. “Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları Ve Cu(II) Ve Ni(II) Komplekslerinin Sentezi Ve Karakterizasyonu”. Journal of the Institute of Science and Technology, c. 12, sy. 3, 2022, ss. 1665-76, doi:10.21597/jist.1102515.
Vancouver Atik B, Demetgül C. Polihedral Oligomerik Silseskioksan (POSS) Bileşiklerinin Schiff Bazları ve Cu(II) ve Ni(II) Komplekslerinin Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der. 2022;12(3):1665-76.