Synthesis of Some Novel Alkoxysilyl-functionalized Ionic Liquids

Öz

The field of ionic liquid (IL) compounds has recently become one of the popular topics because of its green chemistry potential and superior properties. A series of some novel alkoxysilyl-functionalized ionic liquids which containing different hydrophobic chains have been synthesized and their structures were identified by infrared spectrometer (FT-IR), nuclear magnetic resonance spectrometer (NMR). Termal stabilities were investigated of synthesized ionic liquids. Synthesized ionic liquid compounds are good candidates for different application area due to their functional group which involves easy attachment of them on the surface of supported materials.

Anahtar Kelimeler

• Alkoxysilyl-functionalized ionic liquid,dihydroimidazolium

Kaynakça

1. 1. Bonhoˆte, P, Dias AP, Papageorgiou, N, Kalyanasundaram, K, Gratzel M. 1996. Hydrophobic, Highly Conductive Ambient-Temperature Molten Salts, Inorg. Chem; 35: 1168-1178.
2. 2. Huddleston, JG, Visser, AE, Reichert, WM, Willauer HD, Broker, GA, Rogers, RD. 2001. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation, Green Chemistry; 3: 156–164.
3. 3. Dzyuba, SV, Bartsch, RA. 2002. Influence of Structural Variations in 1-Alkyl(aralkyl)-3-MethylimidazoliumHexafluorophosphates and Bis(trifluoromethyl-sulfonyl)imides on Physical Propertiesof the Ionic Liquids, ChemPhysChem; 3: 161-166.
4. 4. Wilkes, JS. 2004. Properties of ionic liquid solvents for catalysis, Journal of Molecular Catalysis A: Chemical; 214: 11–17.
5. 5. Seddon KR. 1997. Ionic Liquids for Clean Technology, Journal of Chemical Technology & Biotechnology; 68: 351-356.
6. 6. Welton, T. 1999. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis, Chemical Review; 99: 2071−2083.
7. 7. Itoh, T. 2017. Ionic Liquids as Tool to Improve Enzymatic Organic Synthesis, Chemical Review; 117: 10567−10607.
8. 8. Hidayaha, NN, Abidin, SZ. 2017. The evolution of mineral processing in extraction of rare earth elements using solid-liquid extraction over liquid-liquid extraction: A review Minerals Engineering; 112: 103–113.

9. 9. Meksi, N, Moussa, A. 2017. A review of progress in the ecological application of ionic liquids in textile processes, Journal of Cleaner Production; 161: 105-126.
10. 10. Shah, NK, Pati, RK, Ray, A, Mukhopadhyay, I. 2017. Electrodeposition of Si from an Ionic Liquid Bath at Room Temperature in the Presence of Water, Langmuir; 33: 1599−1604.
11. 11. Pereira, NM, Brincoveanu, O , Pantazi, AG, Pereira, CM, Araújo, JP , Silva, AF, Enachescu, M , Anicai, L. 2017. Electrodeposition of Co and Co composites with carbon nanotubes using choline chloride-based ionic liquids, Surface & Coatings Technology; 324: 451–462.
12. 12. Dupre, N, Moreau, P, Vito, ED, Quazuguel, L, Boniface, M, Kren, H, Bayle-Guillemaud, P, Guyomard, D. 2017. Carbonate and Ionic Liquid Mixes as Electrolytes To Modify Interphases and Improve Cell Safety in Silicon-Based Li-Ion Batteries, Chemistry of Materials; 29: 8132−8146.
13. 13. Lennert, A, Sternberg, M, Meyer, K, Costa, RD, Guldi, DM. 2017. Iodine-Pseudohalogen Ionic Liquid-Based Electrolytes for QuasiSolid-State Dye-Sensitized Solar Cells, ACS Applied. Materials &. Interfaces; 9: 33437−33445.
14. 14. Nadar, SS, Pawar, RG, Rathod, VK. 2017. Recent advances in enzyme extraction strategies: Acomprehensive review. International Journal of Biological Macromolecules; 101: 931–957.
15. 15. Ongun MZ. 2019. Development of Highly Sensitive Metal-Free TetraphenylporphyrinBased Optical Oxygen Sensing Materials along with ILs and AgNPs, Celal Bayar University Journal of Science; 15(1): 131-138.
16. 16. Saugar, AI, Márquez-Alvarez, C, Pérez-Pariente, J. 2017. Direct synthesis of bulk AlPON basic catalysts in ionic liquids, Journal of Catalysis; 348: 177–188.
17. 17. Elhamifar, D, Eram, A, Moshkelgosha, R. 2017. Ionic liquid and ethyl-based bifunctional ordered nanoporous organosilica supported palladium: An efficient catalyst for homocoupling of phenylacetylenes, Microporous and Mesoporous Materials; 252: 173-178.
18. 18. Sert E, Atalay FS. 2017. Application of Green Catalysts for the Esterification of Benzoic Acid with Different Alcohols, Celal Bayar University Journal of Science; 13(4): 907-912.
19. 19. Laali, KK. 2016. Ionic liquids as novel media for electrophilic/onium ion chemistry and metal-mediated reactions: a progress summary ARKIVOC (i) 150-171.
20. 20. Welton, T. 2004, Ionic liquids in catalysis, Coordination Chemistry Reviews; 248: 2459–2477.
21. 21. Lee, S-G. 2006. Functionalized imidazolium salts for task-specific ionic liquids and their applications, Chemical Communications; 10: 1049–1063.
22. 22. Borja, G, Pleixats, R, , Bied, C, Moreaub, JJE. 2008. Recoverable Palladium Catalysts for Suzuki–Miyaura CrossCoupling Reactions Based on Organic-Inorganic Hybrid Silica Materials Containing Imidazolium and Dihydroimidazolium Salts. Advanced Synthesis & Catalysis; 350: 2566 – 2574.
23. 23. Trilla, M, Pleixats, R, Man, MWC, Bied, C. 2009. Organic–inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts as recyclable organocatalysts for Knoevenagel condensations, Green Chemistry; 11: 1815–1820.
24. 24. Mehnert, CP, Cook, RA, Dispenziere, NC, Afeworki, M. 2002. Supported Ionic Liquid Catalysis - A New Concept for Homogeneous Hydroformylation Catalysis, Journal of the American Chemical Society; 120: 12932-12933.
25. 25. Türkmen, H, Ceyhan, N, Karabay, Yavasoglu, NÜ, Özdemir, G, Çetinkaya, B. 2011. Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents, European Journal of Medicinal Chemistry; 46: 2895-2900.
26. 26. van der Made, AW, van der Made, RH. 1993. A Convenient Procedure for Bromomethylation of Aromatic Compounds. Selective Mono-, Bis-, or Trisbromomethylation, The Journal of Organic Chemistry; 58: 1262-1263.
27. 27. Jia W, Wu Y, Huang J, An Q, Xu D, Wu Y, Lib F, Li G. 2010. Poly(ionic liquid) brush coated electrospun membrane: a useful platform for the development of functionalized membrane systems, Journal of Materials Chemistry; 20: 8617–8623.
28. 28. Aksın O, Turkmen H, Artok L, Cetinkaya B, Ni C, Büyükgüngör O, Özkal E. 2006. Effect of immobilization on catalytic characteristics of saturated Pd-N-heterocyclic carbenes in Mizoroki–Heck reactions, Journal of Organometallic Chemistry; 691 3027–3036.
29. 29. Stathatos E, Jovanovski V, Orel B, Jerman I, Lianos P. 2007. Dye-Sensitized Solar Cells Made by Using a Polysilsesquioxane Polymeric Ionic Fluid as Redox Electrolyte The Journal of Physical Chemistry C; 111: 6528-6532.
30. 30. Grishina, EP, Ramenskaya, LM, Gruzdev, MS, Kraeva OV. 2013. Water effect on physicochemical properties of 1-butyl-3-methylimidazolium based ionic liquids with inorganic anions, Journal of Molecular Liquids; 177: 267–272.
31. 31. Ngo, HL, LeCompte, K, Hargens, L, McEwen, AB. 2000. Thermal properties of imidazolium ionic liquids, Thermochimica Acta, 357-358, 97-102.
32. 32. Billard, I, Mekki, S, Gaillard, C, Hesemann, P, Moutiers, G, Mariet C, Labet, A, Bünzli, JCG. 2004. Eu III Luminescence in a Hygroscopic Ionic Liquid: Effect of Water and Evidence for a Complexation Process, European Journal of Inorganic Chemistry; 6: 1190-1197.
33. 33. Anthony, JL, Maginn, EJ, Brennecke, JF. 2001. Solution Thermodynamics of Imidazolium-Based Ionic Liquids and Water, The Journal of Physical Chemistry B; 105: 10942-10949.
34. 34. Perissi I, Bardi U, Caporali S, Lavacchi A, 2006. High temperature corrosion properties of ionic liquids. Corrosion Science; 48: 2349–2362.