Investigation of the Gelation Potential of Low Molecular Weight Organogelator

Yıl 2022, , 18 - 21, 30.06.2022

Deniz Barış Cebe , Murat Sunkur

https://doi.org/10.36222/ejt.1106639

Öz

In this study, low molecular weight amide compound was employed as the organogelator and its gelation potential was investigated with various solvents. The morphological properties of the obtained gels were investigated. The network structure of the obtained gel was determined by scanning electron microscopy (SEM). Fatty acid esters used in the cosmetic and pharmaceutical industries and also solvents commonly used in the laboratory were employed for gelation. According to this process, the organogelator formed a gel with all the fatty acid esters at very low concentrations and with only anisole, xylene, liquid paraffin and n-dodecane of common organic solvents. Among the gels obtained, those with the lowest concentration were made with isopropyl laurate and isopropyl myristate. It was determined that the melting temperature of the gels prepared with fatty acid esters was higher than those prepared in common solvents. The organogel with the highest melting temperature is the gels made with isopropyl myristate and isopropyl palmitate. In addition, gelation enthalpy values ΔHg were found. According to the results obtained, it was determined that the highest ΔHg value belonged to the gel prepared with isopropyl laurate.

Anahtar Kelimeler

Gelation, Tetraamide compounds, Low Molecular Weight Organogelator

Kaynakça

• [1] Vintiloiu, A., Leroux, J. C., Organogels and Their Use in Drug Delivery–A review, J. Control. Release, 125 (2008), pp. 179-192.
• [2] Terech, P., Weiss, R. G., Low Molecular Mass Gelators of Organic Liquids and the Properties of Their Gels, Chem. Rev., 97 (1997), pp. 3133-3159.
• [3] Van Esch, J., Feringa, B. L., New Functional Materials Based on Self-Assembling Organogels: from Serendipity Towards Design, Angew. Chem. Int. Ed., 13 (2000), pp. 2263-2265.
• [4] Murdan, S., Organogels in Drug Delivery, Expert Opin. Drug Deliv., 2 (2005), pp. 489-505.
• [5] Heeres, A., Pol, C. van der, Stuart, M., Friggeri, A., Feringa, B. L., Esch, J. van, Orthogonal Self-Assembly of Low Molecular Weight Hydrogelators and Surfactants, J. Am. Chem. Soc., 125 (2003), pp. 14252-14253.
• [6] Kobayashi, H., Friggeri, A., Koumoto, K., Amaike, M., Shinkai, S., Reinhoudt, D. N., Molecular Design of ‘‘Super’’ Hydrogelators: Understanding the Gelation Process of Azobenzene-Based Sugar Derivatives in Water, Org. Lett., 4 (2002), pp. 1423-1426.
• [7] Abdallah, D. J., Weiss, R. G., Organogels and Low Molecular Mass Organic Gelators, Adv. Mater., 12 (2000), pp. 1237-1247.
• [8] Gronwald, O., Shinkai, S., Sugar-Integrated Gelators of Organic Solvents, Chem. Eur. J., 7 (2001), pp. 4328-4334.
• [9] Baris Cebe D., Ekmen M., Investigation of the Gelation Properties of L-Isoleucine Derivative Tetraamide Compounds, Fresenius Environ. Bull., 31 (2022), 03A, pp. 3819-3827.
• [10] Branco, M. C., Pochan, D. J., Wagner, N. J., Schneider, J. P., Macromolecular Diffusion and Release from Self-Assembled β-hairpin Peptide Hydrogels, Biomaterials, 30 (2009), pp. 1339-1347.
• [11] Murdan, S., Bergh, V. D., Gregoriadis, G., Florence, A. T., Water-in-Sorbitan Monostearate Organogels (Water-in-Oil Gels), J. Pharm. Sci., 88 (1999), pp. 615-619.
• [12] Zhou, S. L., Matsumoto, S., Tian, H. D., Yamane, H., Ojida, A., Kiyonaka, S., Hamachi, I., pH-Responsive Shrinkage/Swelling of A Supramolecular Hydrogel Composed of Two Small Amphiphilic, Chem. Eur. J., 11 (2005), pp. 1130-1136.
• [13] Zhang, Y., Gu, H., Yang, Z., Xu, B., Supramolecular Hydrogels Respond to Ligand−Receptor Interaction, J. Am. Chem. Soc., 125 (2003), 45, pp. 13680-13681.
• [14] Sunkur, M., Aydın, S., Aral, T., Dağ, B., Erenler, R., Preparation of New Mono- and Bis-Amide Derivatives of L-isoleucine via Amidation of Carboxyl and Amino Groups, Org. Commun., 14 (2021), 3, pp. 294-299.
• [15] Hanabusa, K., Yamada, M., Kimura, M., Shirai, H., Prominent Gelation and Chiral Aggregation of Alkylamides Derived from trans-1,2-diaminocyclohexane, Angew. Chem. Int. Ed., 35 (1996), pp. 1949-1951.
• [16] Xudong, Y., Li, Y., Yin, Y., Yu, D., A Simple and Colorimetric Fluoride Receptor and its Fluoride-Responsive Organogel, Mater. Sci. Eng. C, 32 (2012), pp. 1695-1698.
• [17] Seo, S. H., Chang, J. Y., Organogels from 1H-imidazole Amphiphiles: Entrapment of a Hydrophilic Drug into Strands of the Self-Assembled Amphiphiles, Chem. Mater., 17 (2005), pp. 3249-325.
• [18] Suzuki, M., Yumoto, M., Shirai, H., Hanabusa, K., Supramolecular Gels Formed by Amphiphilic Low-Molecular-Weight Gelators of N-alpha,N-epsilon-diacyl-L-lysine Derivatives, Chem. Eur. J., 14 (2008), pp. 2133-2144.
• [19] George, M., Weiss, R. G., Molecular Organogels. Soft Matter Comprised of Low-Molecular-Mass Organic Gelators and Organic Liquids, Acc. Chem. Res., 39 (2006), pp. 489-497.
• [20] Suzuki, M., Saito, H., Hanabusa, K., Two-Component Organogelators Based on Two L-Amino Acids: Effect of Combination of L-Amino Acids on Organogelation Behavior, Langmuir, 25 (2009), pp. 8579-8585.