Login Register Cart 0
Generic placeholder image

Current Physical Chemistry

Editor-in-Chief

ISSN (Print): 1877-9468
ISSN (Online): 1877-9476

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Effect of Laterally Substituted Methoxy Group on the Liquid Crystalline Behavior of Novel Ester Molecules

Author(s): Neha K. Baku, Jwalant J. Travadi* and Kartik D. Ladva

Volume 14, Issue 1, 2024

Published on: 04 October, 2023

Page: [20 - 31] Pages: 12

DOI: 10.2174/1877946813666230809121625

Price: $65

Abstract

Background: The aim of this research is to study the effect of length-to-width ratio on mesomorphism to enhance the understanding of its potential applications. This will be achieved by synthesizing a unique and innovative series of identical ester molecules, including lateral methoxy groups and terminal ethyl benzoate groups. In this research, we aim to find new insights into the relationship between molecular structures and mesomorphic behaviors, which could have significant implications for the development of advanced materials with adapted properties.

The objective of the study is to investigate the mesophase behavior of new ester mesogens and determine how they are influenced by lateral methoxy groups. By identifying the underlying perspectives and relationships between these variables, we hope to better understand the unique properties and potential applications of these materials.

Method: In this research work, the focus is on the synthesis of ethyl(E)-4-((3-(4-alkoxy-3- methoxyphenyl)acryloyl)oxy)benzoate, which is prepared from Steglich esterification method by using (E)-3-(4-alkoxy-3-methoxyphenyl)acrylic acid and ethyl 4- hydroxybenzoate. Synthesis processes involve precise reaction sequences designed to ensure maximum yield and purity of the final product. By providing a detailed report on the experimental process, this study contributes to the ongoing research efforts aimed at the development of innovative compounds with various applications in liquid crystals.

Result: A new set of liquid crystal derivatives has been synthesized and studied to investigate the effect of molecular structure on the behavior of liquid crystals, with particular attention to the group -OCH3 located laterally. This series was composed of 12 derivatives (C1-C16). Among them, the first six derivatives (C1-C6) did not have the characteristics of a liquid crystal, while the remaining derivatives (C7 and C8) had a monotropic behavior, and C10-C16 had an enantiotropic smectogenic liquid crystal behavior without exhibition of the nematic phase. The average thermal stability of the smectic property was 87.33 °C, and the mesophase range was 2 °C to 14 °C. The molecular structure was confirmed by analytical and spectral analysis. The properties of liquid crystals of this new series were compared with those of other known structurally similar homologous series. The transition temperatures were determined with an optical polarizing microscope equipped with a heating phase.

Conclusion: The mesomorphic thermal and optical properties of the compounds have been validated by DSC and POM techniques. The result shows that the length of the alkyl chain has a significant influence on the mesomorphic characteristics and thermal stability of the different mesophases. Evaluation of the compounds studied indicates that the molecules are sensitive to their lateral substituent, which influences the thermal characteristics and stability of the mesophase.

Keywords: Liquid crystals, smectic, mesomorphism, ester, DSC, POM.

« Previous Next »
[1]
Nada, S.; Hagar, M.; Farahat, O.; Hasanein, A.A.; Emwas, A.H.; Sharfalddin, A.A.; Jaremko, M.; Zakaria, M.A. Three rings schiff base ester liquid crystals: Experimental and computational approaches of mesogenic core orientation effect, heterocycle impact. Molecules, 2022, 27(7), 2304.
[http://dx.doi.org/10.3390/molecules27072304] [PMID: 35408703]
[2]
Lagerwall, J.P.F.; Scalia, G. A new era for liquid crystal research: Applications of liquid crystals in soft matter nano-, bio- and microtechnology. Curr. Appl. Phys., 2012, 12(6), 1387-1412.
[http://dx.doi.org/10.1016/j.cap.2012.03.019]
[3]
Wang, Y.; Sun, J.; Liao, W.; Yang, Z. Liquid crystal elastomer twist fibers toward rotating microengines. Adv. Mater., 2022, 34(9), 2107840.
[http://dx.doi.org/10.1002/adma.202107840] [PMID: 34933404]
[4]
Gao, J.; Tian, M.; He, Y.; Yi, H.; Guo, J. Multidimensional encryption in emissive liquid crystal elastomers through synergistic usage of photorewritable fluorescent patterning and reconfigurable 3D shaping. Adv. Funct. Mater., 2022, 32(4), 2107145.
[http://dx.doi.org/10.1002/adfm.202107145]
[5]
Ula, S.W.; Traugutt, N.A.; Volpe, R.H.; Patel, R.R.; Yu, K.; Yakacki, C.M. Liquid crystal elastomers: An introduction and review of emerging technologies. Liq. Cryst. Rev., 2018, 6(1), 78-107.
[http://dx.doi.org/10.1080/21680396.2018.1530155]
[6]
Jiang, Z.C.; Xiao, Y.Y.; Tong, X.; Zhao, Y. Selective decrosslinking in liquid crystal polymer actuators for optical reconfiguration of origami and light fueled locomotion. Angew. Chem. Int. Ed., 2019, 58(16), 5332-5337.
[http://dx.doi.org/10.1002/anie.201900470] [PMID: 30816599]
[7]
Khalid, M.; Shanks, K.; Ghosh, A.; Tahir, A.; Sundaram, S.; Mallick, T.K. Temperature regulation of concentrating photovoltaic window using argon gas and polymer dispersed liquid crystal films. Renew. Energy, 2021, 164, 96-108.
[http://dx.doi.org/10.1016/j.renene.2020.09.069]
[8]
Ahmad, F.; Luqman, M.; Jamil, M. Advances in the metal nanoparticles (MNPs) doped liquid crystals and polymer dispersed liquid crystal (PDLC) composites and their applications - a review. Mol. Cryst. Liq. Cryst. , 2021, 731(1), 1-33.
[http://dx.doi.org/10.1080/15421406.2021.1954759]
[9]
Bubnov, A.; Cigl, M.; Penkov, D.; Otruba, M.; Pociecha, D.; Chen, H.H.; Hamplová, V. Design and self-assembling behaviour of calamitic reactive mesogens with lateral methyl and methoxy substituents and vinyl terminal group. Polymers, 2021, 13(13), 2156.
[http://dx.doi.org/10.3390/polym13132156] [PMID: 34208990]
[10]
Naemura, S. Advanced LCD technologies. Displays, 2001, 22(1), 1.
[http://dx.doi.org/10.1016/S0141-9382(01)00046-4]
[11]
Kim, W.S.; Elston, S.J.; Raynes, E.P. Hybrid method for modelling light leakage by a spherical object in a liquid crystal layer. Displays, 2008, 29(5), 458-463.
[http://dx.doi.org/10.1016/j.displa.2008.03.004]
[12]
Vertogen, G.; De Jeu, W.H. Thermotropic Liquid Crystals, Fundamentals; Springer-Verlag, 1988.
[13]
Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Friend, R.H.; MacKenzie, J.D. Efficient organic photovoltaics from soluble discotic liquid crystalline materials. Physica E, 2002, 14(1-2), 263-267.
[http://dx.doi.org/10.1016/S1386-9477(02)00400-9]
[14]
Arakawa, Y.; Inui, S.; Tsuji, H. Synthesis, phase transitions, and liquid crystal behavior of alkylthio azobenzenes. Tetrahedron, 2022, 122(132958), 132958.
[http://dx.doi.org/10.1016/j.tet.2022.132958]
[15]
Al-Obaidy, M.M.A.R.; Tomi, I.H.R.; Abdulqader, A.M. Synthesis and study the liquid crystalline behaviors of double Schiff bases bearing ester linkage as a central core. Liq. Cryst., 2022, 49(1), 131-141.
[http://dx.doi.org/10.1080/02678292.2021.1945693]
[16]
Tamura, K.; Uchida, H.; Hori, K. Influence of Directions of Two Ester Linkages on Crystal Structures of Isomeric Mesogens. Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals, 1999, 330(1), 201-206.
[http://dx.doi.org/10.1080/10587259908025592]
[17]
Ranchchh, A.R.; Tharesha, B.R.; Bhoya, U.C. Dependence of Mesomorphism in Combination with Fluoro and Chloro Groups. Mol. Cryst. Liq. Cryst. , 2018, 675(1), 49-58.
[http://dx.doi.org/10.1080/15421406.2019.1624034]
[18]
Alnoman, R.B.; Hagar, M.; Ahmed, H.A.; Naoum, M.M.; Sobaih, H.A.; Almshaly, J.S.; Haddad, M.M.; Alhaisoni, R.A.; Alsobhi, T.A. Binary liquid crystal mixtures based on schiff base derivatives with oriented lateral substituents. Crystals, 2020, 10(4), 319.
[http://dx.doi.org/10.3390/cryst10040319]
[19]
Jamain, Z.; Azman, A.N.A.; Razali, N.A.; Makmud, M.Z.H. A review on mesophase and physical properties of cyclotriphosphazene derivatives with schiff base linkage. Crystals, 2022, 12(8), 1174.
[http://dx.doi.org/10.3390/cryst12081174]
[20]
Travadi, J.J. The effect of laterally substituted methoxy group on mesomorphicity. Int. J. Res. Appl. Sci. Eng. Technol., 2018, 6(3), 2164-2166.
[http://dx.doi.org/10.22214/ijraset.2018.3341]
[21]
Zakaria, M.A.; Alazmi, M.; Katariya, K.D.; El Kilany, Y.; El Ashry, E.S.H.; Jaremko, M.; Hagar, M.; Mohammady, S.Z. Mesomorphic behaviour and DFT insight of arylidene schiff base liquid crystals and their pyridine impact investigation. Crystals, 2021, 11(8), 978.
[http://dx.doi.org/10.3390/cryst11080978]
[22]
Vadodaria, M.S. Synthesisof novel ester series and study of its mesomorphism dependence on terminal end group with lateral -OCH3 Group. Mol. Cryst., 2016, 624.
[http://dx.doi.org/10.1080/15421406.2015.1044158]
[23]
Fahmi, A.A.; Saad, G.R.; Ali, M.H.; Ahmed, N.H.S. Steric effect of di-lateral methyl substituent on the mesophase behavior of four-ring azo/ester/azo homologues. Liq. Cryst., 2022, 49(11), 1511-1523.
[http://dx.doi.org/10.1080/02678292.2022.2044528]
[24]
Al-Hamdani, U.J.; Abdulwahhab, H.A.; Hussein, K.A. Effects of terminal substituents on mesomorphic properties of Schiff base – ester mesogens and DFT calculations. Liq. Cryst., 2022, 49(14), 1998-2007.
[http://dx.doi.org/10.1080/02678292.2022.2091803]
[25]
Dave, J.S.; Vora, R.A. Liquid Crystals and Ordered Fluids, Liquid Crystals and Ordered Fluids; Liquid Crystals and Ordered Fluids, 1970.
[26]
Vogel, A. Text Book of Practical Organic Chemistry; ELBS and Longman: London, 1989.
[27]
Chauhan, M.L.; Pandya, R.N.; Doshi, A.V. Synthesis and mesomorphism of novel liquid crystalline: p -(p ′- n -Alkoxy Benzoyloxy) methyl cinnamates. Mol. Cryst. Liq. Cryst. (Phila. Pa.), 2011, 548(1), 228-234.
[http://dx.doi.org/10.1080/15421406.2011.591664]
[28]
Suthar, D.M.; Doshi, A.A.; Doshi, A.V. Synthesis and evaluation of a novel liquid crystalline homologous series: α-4-[4′- n -Alkoxy Cinnamoyloxy] Benzoyl-β-3″,4″-dimethoxy phenyl ethylenes. Mol. Cryst. Liq. Cryst. (Phila. Pa.), 2013, 577(1), 51-58.
[http://dx.doi.org/10.1080/15421406.2013.785812]
[29]
Bhoya, U.C.; Vyas, N.N.; Doshi, A.V. Determination of latent mesogenic behavior in nonmesogenic compounds by extrapolation method. Mol. Cryst. Liq. Cryst. , 2012, 552(1), 104-110.
[http://dx.doi.org/10.1080/15421406.2011.604590]
[30]
Patel, P.K.; Patel, R.B.; Shah, R.R. Mesomorphic properties of liquid crystalline compounds with central linkage chalconyl ester and laterally substituted bromo group. Chemistry, 2016, 202(1)
[31]
Gray, G.W. The influence of molecular structure on liquid crystalline properies. Mol. Cryst., 1966, 1(2), 333-349.
[http://dx.doi.org/10.1080/15421406608083277]
[32]
Gray, G.W. Advances in synthesis and the role of molecular geometry in liquid crystallinity. Mol. Cryst., 1969, 7(1), 127-151.
[http://dx.doi.org/10.1080/15421406908084868]
[33]
Vadodaria, M.S.; Ladva, K.D.; Doshi, A.V.; Travadi, J.J. Mesomorphism dependence on lateral substitution and central bridge. Mol. Cryst. Liq. Cryst. , 2016, 624(1), 103-111.
[http://dx.doi.org/10.1080/15421406.2015.1044637]
[34]
Doshi, A.V.; Joshi, C.G. a; Chauhan, M.L. Synthesis and study of ester homologous series of mesogenic characteristics: p-Isobutyloxy Phenyl-p’-n-alkoxy benzoates. Pharma Chem., 2011, 3(5), 226-232.
[35]
Lohar, J.M.; Mashru, U. Mesomorphic behavior of some esters:Ethyl p-(p′-n-Alkoxycinnamoyloxy). Benzoates. J. Indian Chem. Soc., 1980, 57, 904-908.
[http://dx.doi.org/10.5281/ZENODO.6371950]
[36]
Travadi, J.J.; Vadodaria, M.S.; Ladva, K.D.; Doshi, A.V. Mesomorphism dependence on molecular flexibility. Mol. Cryst. Liq. Cryst. , 2016, 630(1), 69-78.
[http://dx.doi.org/10.1080/15421406.2016.1146867]
[37]
Abramczyk, H.; Kolodziejski, M.; Waliszewska, G. Raman spectra of phenylacetylene in acetonitrile and methylcyclohexane at low temperatures. 2. structural order and vibrational relaxation in frozen matrices at 77 K. J. Phys. Chem., 1998, 102, 7765.
[http://dx.doi.org/10.1021/jp9818840]

Rights & Permissions Print Cite
Article Metrics
23
2
© 2024 Bentham Science Publishers | Privacy Policy