Mesomorphism Dependence on Chalconyl Derivative with Heterocyclic Tail and Methoxy Lateral Group

ABSTRACT

A new homologous series of liquid crystal (LC) materials incorporating a heterocyclic ring was synthesized to investigate and establish the relationship between molecular structure and liquid crystal properties. The series comprises 12 members, labeled A₁ to A₁₂. Among them, A₈ to A₁₂ exhibit monotropic nematic phases. Comparative studies between mesomorphic and non-mesomorphic members were conducted, leading to several important conclusions. Transition temperatures were measured using a polarizing optical microscope equipped with a heating stage. Analytical and spectral analyses confirmed the molecular structures of the homologues. This series is classified as having middle-ordered melting characteristics. The LC properties of this new series were also compared with those of structurally related known series.

Reference

• [1] Rakhasia, P. K.; Ranchchh, A. R.; Bhoya, U. C. Molecular Flexibility Dependence on Mesogenic Behaviors of Isomeric and Nonisomeric Series. Cryst. Liq. Cryst. 2017, 643 (1), 159–167. https://doi.org/10.1080/15421406.2016.1263119.
• [2] Jain, B. B.; Patel, R. B. Synthesis and Study of New Homologous Series of Ester-Chalcone Exhibiting Nematic Phases. Cryst. Liq. Cryst. 2016, 638 (1), 35–43. https://doi.org/10.1080/15421406.2016.1217711.
• [3] Rakhasia, P. K.; Bhola, G. N.; Bhoya, U. C. Study of the Effect of Chalconyl Central Bridge on Mesomorphism. Lett. Chem. Phys. Astron. 2015, 61, 19–27. https://doi.org/10.56431/p-du8g5v.
• [4] Parra, M. L.; Elgueta, E. Y.; Ulloa, J. A.; Vergara, J. M.; Sanchez, A. I. Columnar Liquid Crystals Based on Amino-1,3,4-Thiadiazole Derivatives. Cryst. 2012, 39 (8), 917–925. https://doi.org/10.1080/02678292.2012.686635.
• [5] Prajapati, A. K.; Bonde, N. L. Mesogenic Benzothiazole Derivatives with a Polar Nitro Substituent. Cryst. Liq. Cryst. 2009, 501 (1), 72–85. https://doi.org/10.1080/15421400802697616.
• [6] Foo, K.-L.; Ha, S.-T.; Yeap, G.-Y.; Lin, H.-C. Synthesis and Mesomorphic Behaviors of a Series of Heterocyclic Pyridine-Imine-Ester Based Liquid Crystals. Phase Transit. 2019, 92 (10), 916–930. https://doi.org/10.1080/01411594.2019.1659265
• [7] Ong, L.-K.; Ha, S.-T.; Yeap, G.-Y.; Lin, H.-C. Heterocyclic Pyridine-Based Liquid Crystals: Synthesis and Mesomorphic Properties. Cryst. 2018, 45 (11), 1574–1584. https://doi.org/10.1080/02678292.2018.1455225.
• [8] Lai, L.-L.; Wang, C.-H.; Hsieh, W.-P.; Lin, H.-C. Synthesis and Characterization of Liquid Crystalline Molecules Containing the Quinoline Unit. Cryst. Liq. Cryst. Sci. Technol. Sect. Mol. Cryst. Liq. Cryst. 1996, 287 (1), 177–181. https://doi.org/10.1080/10587259608038754.
• [9] Ha, S.-T.; Koh, T.-M.; Lee, S.-L.; Yeap, G.-Y.; Lin, H.-C.; Ong, S.-T. Synthesis of New Schiff Base Ester Liquid Crystals with a Benzothiazole Core. Cryst. 2010, 37 (5), 547–554. https://doi.org/10.1080/02678291003710425.
• Seed, A. Synthesis of Self-Organizing Mesogenic Materials Containing a Sulfur-Based Five-Membered Heterocyclic Core. Soc. Rev. 2007, 36 (12), 2046. https://doi.org/10.1039/b612666a.
• Kotian, S. Y.; Mohan, C. D.; Merlo, A. A.; Rangappa, S.; Nayak, S. C.; Rai, K. M. L.; Rangappa, K. S. Small Molecule Based Five-Membered Heterocycles: A View of Liquid Crystalline Properties beyond the Biological Applications. Mol. Liq. 2020, 297, 111686. https://doi.org/10.1016/j.molliq.2019.111686.
• Han, J.; Zhang, F.-Y.; Wang, J.-Y.; Wang, Y.-M.; Pang, M.-L.; Meng, J.-B. Synthesis and Comparative Study of the Heterocyclic Rings on Liquid Crystalline Properties of 2,5-Aryl-1,3,4-Oxa(Thia)Diazole Derivatives Containing Furan and Thiophene Units. Cryst. 2009, 36 (8), 825–833. https://doi.org/10.1080/02678290903067811.
• Bhola, G. N.; Bhoya, U. C. Mesomorphism Dependence on Heterocyclic End Group. Cryst. Liq. Cryst. 2016, 625 (1), 11–19. https://doi.org/10.1080/15421406.2015.1068972.
• Rakhasia, P. K.; Bhola, G. N.; Bhoya, U. C. Mesomorphism Dependence of Chalconyl Derivatives on Position of -CH=CH- Unit. Cryst. Liq. Cryst. 2016, 626 (1), 81–89. https://doi.org/10.1080/15421406.2015.1106280.
• Bhola, G. N.; Bhoya, U. C. Mesomorphism Dependence on Cis-Trans Configuration and Varying Terminal/Lateral Group. Lett. Chem. Phys. Astron. 2016, 65, 71–79. https://doi.org/10.56431/p-9v83m3.
• Muniya, N. R.; Patel, V. R. Study of Mesomorphism and Its Relation to Molecular Structure through Molecular Rigidity and Flexibility. Cryst. Liq. Cryst. 2016, 638 (1), 77–85. https://doi.org/10.1080/15421406.2016.1221975.
• Kotadiya, V. C.; Khunt, M. D.; Bhoya, U. C. Study of Molecular Structure, Mesomorphism and Their Relation with Molecular Rigidity-Flexibility. Cryst. Liq. Cryst. 2016, 626 (1), 45–57. https://doi.org/10.1080/15421406.2015.1106247.
• Hasan, A.; Abbas, A.; Akhtar, M. N. Synthesis, Characterization and Fluorescent Property Evaluation of 1,3,5-Triaryl-2-Pyrazolines. Molecules 2011, 16 (9), 7789–7802. https://doi.org/10.3390/molecules16097789.
• Dave, J. S.; Vora, R. A. Mesomorphic Behaviour of the Cholesteryl Esters-I: P-n-Alkoxybenzoates of Cholesterol. In Liquid Crystals and Ordered Fluids; Johnson, J. F., Porter, R. S., Eds.; Springer US: Boston, MA, 1970; pp 477–487. https://doi.org/10.1007/978-1-4684-8214-0_38.
• Yeap, G.-Y.; Susanti, I.; Teoh, B.-S.; Kamil Mahmood, W. A.; Harrison, W. T. A. Synthesis and Phase Transition in New Chalcone Derivatives: Crystal Structure of 1-Phenyl-3-(4′-Undecylcarbonyloxyphenyl)-2-Propen-1-One. Cryst. Liq. Cryst. 2005, 442 (1), 133–146. https://doi.org/10.1080/154214090964753.
• Neises, B.; Steglich, W. Simple Method for the Esterification of Carboxylic Acids. Chem. Int. Ed. Engl. 1978, 17 (7), 522–524. https://doi.org/10.1002/anie.197805221.

• Bhola, G. N.; Bhoya, U. C. Mesomorphism Dependence on Heterocyclic Tail. Cryst. Liq. Cryst. 2016, 625 (1), 30–37. https://doi.org/10.1080/15421406.2015.1068975.

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