Synthesis, Characterization and Liquid Crystal Properties of some Chalcone-Schiff Bases Compounds
DOI:
https://doi.org/10.22401/ANJS.29.2.01Keywords:
Mesomorphic, Azomethine, Chalcone, Linearity, 4-aminoacetophenoneAbstract
This research examines the alteration of mesomorphic behavior in azomethine chalcone compounds as liquid crystals, influenced by the linearity of molecule and alkoxy groups’ position. Compounds were synthesized by the reaction of 4-substituted benzaldehydes with 4-aminoacetophenone using catalysts appropriate for the reaction type. Тhe synthesized compounds were characterized using FТ-IR, 1H NМR, and 13C-NМR techniques. Mesomorphic characteristics were examined by differential scanning calorimetry (DSC), while the resultant textures were featured using polarized optical microscopy (POM). Compounds (R1-R3) showed an absence of mesomorphic properties due to the lack of molecular linearity, while compounds (M1-M3) exhibited nematic phases distinguished by a marble-like texture.
References
[1] Müller-Goymann, C.C.; "Physicochemical characterization of colloidal drug delivery systems such as reverse micelles, vesicles, liquid crystals and nanoparticles for topical administration". Eur. J. Pharm. Biopharm., 58 (2): 343–356, 2004.
[2] Stevenson, C. L.; Bennett, D. B.; and Lechuga-Ballesteros, D.; "Pharmaceutical liquid crystals: the relevance of partially ordered systems". J. Pharm. Sci., 94 (9): 1861–1880, 2005.
[3] Jákli, A.; and Saupe, A. "One-and_1 Two-Dimensional Fluids: Properties of Smectic, Lamellar and Columnar Liquid Crystals". 1st ed.;CRC Press: Boca Raton, USA, 2006.
[4] Shen, Y.; and Dierking, I.; "Electrically driven formation and dynamics of swallow-tail solitons in smectic A liquid crystals". Mater. Adv., 2 (14): 4752–4761, 2021.
[5] De Gennes, P. G.; and Prost, J. "The Physics of Liquid Crystals". 2nd ed.; Oxford University Press: Oxford, UK, 1993.
[6] Gao, M.; Kim, Y.; Zhang, C.; Borshch, V.; Zhou, S.; Park, H.; Jákli, A.; Lavrentovich, O. D.; Tamba, M.; and Kohlmeier, A.; "Direct observation of liquid crystals using cryo‐TEM: Specimen preparation and low‐dose imaging". Microsc. Res. Tech., 77 (10): 754–772, 2014.
[7] Smaisim, G. F.; Mohammed, K. J.; Hadrawi, S. K.; Koten, H.; and Kianfar, E.; "Properties and Application of Nanostructure in Liquid Crystals: Review". BioNanoSci.,13: 819–839, 2023.
[8] Oladepo, S. A.; "Development and Application of Liquid Crystals as Stimuli-Responsive Sensors". Molecules ,27,2022.
[9] Bunjes, H.; and Rades, T.; "Thermotropic liquid crystalline drugs". J. Pharm. Pharmacol., 57 (7): 807–816, 2010.
[10] Dierking, I.; and Neto, A. M. F.; "Novel trends in lyotropic liquid crystals". Crystals,10: 1–24, 2020.
[11] Silvestrini, A. V. P.; Caron, A. L.; Viegas, J.; Praça, F. G.; and Bentley, M. V. L. B.; "Advances in lyotropic liquid crystal systems for skin drug delivery". Expert Opin. Drug Deliv.,17: 1781–1805, 2020.
[12] Mohsen, O. A.; Mohammed, S. A.; Hathal, M. M.; Abed, K. M.; and Saleem, A. G.; "The parametric analysis of corrosion rate of carbon steel in sulfuric acid and corrosion inhibition using indole"., 2nd International Conference on Renewable Energy, Kirkuk City, Iraq, 2022, in AIP Conference Proceedings 2885: AIP Publishing, 2024.
[13] Zhang, Q.; Zhou, S.; Zhang, R.; and Bischofberger, I.; "Dendritic patterns from shear-enhanced anisotropy in nematic liquid crystals". Sci. Adv., 9 (2): eabq6820, 2023.
[14] Concellón, A.; Lu, R.-Q.; Yoshinaga, K.; Hsu, H.-F.; and Swager, T. M.; "Electric-field-induced chirality in columnar liquid crystals". J. Am. Chem. Soc., 143 (24): 9260–9266, 2021.
[15] Zang, T.; Fu, S.; Cheng, J.; Zhang, C.; Lu, X.; Hu, J.; Xia, H.; and Zhao, Y.; "4D Printing of Shape-Morphing Liquid Crystal Elastomers". Chem Bio Eng., 1 (6): 488–515, 2024.
[16] Katariya, K. D.; Nakum, K. J.; Soni, R.; Soman, S. S.; Nada, S.; and Hagar, M.; "Coumarin Schiff base derivatives: synthesis, mesomorphic properties, photophysical properties and DFT studies". J. Mol. Struct., 1278: 134934, 2023.
[17] Nakum, K. J.; Katariya, K. D.; Savani, C. J.; and Jadeja, R. N.; "The influence of molecular flexibility on the mesogenic behavior of a new homologous series based on azo-azomethine: Synthesis, characterization, photoisomerization and DFT study". J. Mol. Struct., 1249: 131586, 2022.
[18] Masuda, M.; Kobayashi, T.; Kohri, M.; and Kishikawa, K.; "A thermo-birefringence switchable columnar liquid crystalline compound". Mater. Lett., 307: 131055, 2022.
[19] Wang, H.; "Overview of future antenna design for mobile terminals". Engineering, 11: 12–14, 2022.
[20] Zhang, Z.; Yang, X.; Zhao, Y.; Ye, F.; and Shang, L.; "Liquid crystal materials for biomedical applications". Adv. Mater., 35 (36): 2300220, 2023.
[21] Hathal, M. M.; Mohsen, O. A.; Majdi, H. S.; and Hasan, B. O.; "Optimization of Heat Transfer in Solar-Powered Biodiesel Reactors Using Alumina Nanofluids: A Combined Experimental and Numerical Study.". Int. J. Heat Technol., 41 (6) -1397-1406,2023.
[22] Kshash, A. H.; "The effect of hydrogen bonding and azomethine group orientation on liquid crystal properties in benzylidene aniline compounds". Acta Chim. Slov., 67 (3): 739–747, 2020.
[23] Jubair, A. A.; and Kshash, A. H.; "Synthesis, charechterization and mesomorphic properties for 4-bromo-4’-alkanoyloxychalcone". Biochem. Cell. Arch, 22 (1): 3365–3369, 2022.
[24] Taha Yaseen, M.; and Kshash, A. H.; Liquid Crystalline Properties of 4,4’-Methylenebis(N-(4-Alkanoxybenzylidene) Aniline): Synthesis, Characterization, and Theoretical Study. Chem.Soc.Pak ,41(06):1107-1114, 2019.
[25] Mukhlif, M. G.; Mahdi, O. J.; and Bichan, M. J.; "Synthesis, characterization, molecular docking, and computational study of novel spirothiazolidinone compounds". J. Mol. Struct., 1330: 141517, 2025.
[26] Kshash, A. H.; Al-Asafi, O. J. M.; and Salih, H. K.; "Synthesis, Characterization, and Investigation of Mesomorphic Properties of a New 2,5-Bis-(4-alkanoyloxybenzylidene) cyclopentan-1-one". Acta Chim. Slov., 69 (3): 519–525, 2022.
[27] Kshash, A. H.; and Ismail, A. S.; "Minimizing evaporation of light hydrocarbons for iraqi gasoline by using d-glucitol fatty acid esters as reduced pressure agents, synthesis and characterization". Pet. Coal, 61 (1):100-109, 2019.
[28] Kshash, A. H.; "A storage cabinet design for research chemicals for developing nations". J. Chem. Heal. Saf., 26 (4–5): 29–32, 2019.
Downloads
Published
Issue
Section
License
Copyright (c) 2026 Mariam Ali Mohsen, Abdullah Hussein Kshash
This work is licensed under a Creative Commons Attribution 4.0 International License.
.jpg)
