ABSTRACT
A newly synthesized ester homologous series viz Isobutyl-4-(4’-n-alkoxy-3’-methoxy cinnamoyloxy) cinnamates is synthesized to study the effect of branching of the alkyl group. Eleven homologs were synthesized. Among these eleven homologues first seven derivatives C1 to C7 of the investigated series are nonmesomorphic by nature. The rest of the homologs are monotropically smectogenic by nature; thus, the presently investigated series is predominately smectogenic by nature without exhibiting a nematic mesophase. Transition temperatures and textures of synthesized compounds were observed through an optical polarizing microscope equipped with a heating stage. The textures of smectogenic mesophase are focal conic fan-shaped. Some representative members were characterized by IR, 1HNMR, mass spectroscopy and elemental analysis. Transition temperatures of homologues are plotted versus the number of carbon atoms present in n-alkyl chain of left n-alkoxy terminal end group. Isotropic-smectic / smectic-isotropic transition curve behaves in a normal ascending manner. Thermal stability and other mesogenic characteristics are compared with other structurally similar homologous series The mesogenic phase length ranges between 11⁰ C and 22⁰ C and is of the middle-order melting type.
References
- Reinitzer F. Beiträge zur Kenntniss des Cholesterins. Monatshefte für Chemie. 1888;9:421. https://doi.org/10.1007/BF01516710
- Gray GW. Molecular structure and the properties of liquid crystals. London: Academic Press; 1962.
- Demus D. 100 years of liquid crystal chemistry. Mol Cryst Liq Cryst. 1988;165:45.
- Eidenschink R. Liquid crystals—new compounds, new applications. Wiley Online Library. 1989. https://doi.org/10.1002/anie.198914241
- Gray GW, Jones B. Mesomorphism and chemical constitution. Part II. The trans-p-n-alkoxycinnamic acids. J Chem Soc. 1954;0:1467-1470. https://doi.org/10.1039/JR9540001467
- Gray GW. In: Luckhurst GR, Gray GW, editors. The molecular physics of liquid crystals. London: Academic Press; 1979. p. 1-30.
- Pandya SH, Patel VR, Doshi AV. Mesogenic dependence of chalconyl Schiff’s bases on molecular rigidity and flexibility. World Sci News. 2017;86(3):231.
- Eidenschink R, Krause G, Pohl L. German patent DE-B 26366844. 1976.
- Talwee S, Shahi V, Ramteke V, Syed I. Liquid crystals pharmaceutical application: a review. Int J Pharm Res Appl Sci. 2012;1(06).
- Doshi AV, Bhoya UC, Travadi JJ. Determination of latent transition temperatures of nonmesomorphs by extrapolation method in binary systems. Mol Cryst Liq Cryst. 2012;552:10.
- Dave JS, Dewar MJS. Mixed liquid crystals. J Chem Soc. 1954;4617.
- Benbow SJ, Chan AW, Bowsher DR, et al. The prediction of diabetic neuropathic plantar foot ulceration by liquid-crystal contact thermography. Diabetes Care. 1994;17:835.
- Owsik J, Aleksander BS, Elzbieta S. Use of chiral liquid crystals in laser engineering. In: Society of Photo-Optical Instrumentation Engineers (SPIE) Digital Library; 1995. Vol. 2202, p. 185.
- Vora RA, Prajapati AK, Kevat JB, Rao KK. Mesogenic properties and the effect of 1, 2, 4 substitution on the central benzene nucleus: a three-ring mesogens. Liq Cryst. 2001;28:983.
- Baku N, Travadi J, Ladva K. Effect of laterally substituted methoxy group on the liquid crystal behavior of novel ester molecules. Curr Phys Chem. 2023; https://doi.org/10.2174/1877946813666230809121625
- Travadi JJ, Vadodaria MS, Ladva KD, Doshi AV. Study of the effect of lateral substitution on mesogenic behavior with reference to -CH=CH- unit. Mol Cryst Liq Cryst. 2016;626:90.
- Dave JS, Vora RA. Mesomorphic behaviour of the cholesteryl esters-I: p-n-alkoxybenzoates of cholesterol. In: Johnson JF, Porter RS, editors. Liquid Crystals and Ordered Fluids. Boston: Springer; 1970. https://doi.org/10.1007/978-1-4684-8214-0_38
- Vadodaria MS, Ladva KD, Doshi AV, Travadi JJ. Synthesis of novel ester series and study of its mesomorphism dependence on terminal end group with lateral –OCH3 Mol Cryst Liq Cryst. 2016;624:59.
- Chauhan ML, Pandya RN, Doshi AV. Synthesis and mesomorphism of novel liquid crystalline: p-(p′-n-alkoxy benzoyloxy) methyl cinnamates. Mol Cryst Liq Cryst. 2011;548:228. https://doi.org/10.1080/15421406.2011.591664
- Patel RB. Study of the effect of structural variation on mesomorphic characteristics in thermotropic mesogenes [dissertation]. Rajkot: Saurashtra University; 2011.
- Greene TW, Wuts PG. Protective groups in organic synthesis. 2nd ed. New York: John Wiley and Sons; 1991.
- Prajapati AK, Pandya HM. Effect of a lateral chloro group on azomesogens containing the naphthalene moiety. Mol Cryst Liq Cryst. 2003;393:31.
- Jadav ND, Prajapati A, Prajapati AK. Azomesogens containing two fused ring moieties: synthesis and characterization. Mol Cryst Liq Cryst. 2003;399:53.
- Makavana GP, Baku NK, Travadi JJ. Synthesis and study of mesomorphic properties of liquid crystalline compounds involving lateral -OCH3 group and vinyl carboxylate central linkage. World Sci News. 2024;189:116-131.
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