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Mesomorphism in binary mixtures of 4-((hexylimino)methyl)benzoic acid and 4-alkyloxybenzoic acids

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Abstract

A new non-mesogenic Schiff-based carboxylic acid, viz. 4-((hexylimino)methyl)benzoic acid (HIMB), is synthesized and is used to prepare the binary mixtures with mesogenic 4-n-alkyloxybenzoic acids (nOBAs, where n = 3, 4, 5, 7, 8, 9 and 12) in 1:1 molar ratio. The mesomorphism in HIMB and nOBA mixtures is studied by polarizing optical microscopy and differential scanning calorimetry. The mesomorphic thermal stabilities of these mixtures are found to vary with those of the nOBAs. The results are discussed with the reported mixtures of nOBAs with other Schiff-based pyridyl moieties, which are found to exhibit new phase variants and mesomorphic thermal stabilities. The phase transition temperatures and the enthalpy changes at the phase transitions are discussed in comparison with the other similar binary mixtures. The effects of intermolecular interactions on mesomorphism are discussed.

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References

  1. Reinitzer F. Contributions to the knowledge of cholesterol. Monatsch Chem. 1888;9(1):421–441 ibid (English Trans.) Liq Cryst 1989;5:7–18.

  2. Lehmann O. On flowing crystals. Z Phys Chem. 1889;4:462–72.

    Article  Google Scholar 

  3. Friedel G. The mesomorphic states of matter. Ann Phys. 1922;18:273–473.

    Article  CAS  Google Scholar 

  4. Grey GW. Molecular structure and properties of liquid crystals. New York: Academic Press; 1962.

    Google Scholar 

  5. Chandrasekhar S. Liquid crystals. 2nd ed. Cambridge: Cambridge University Press; 1992.

    Book  Google Scholar 

  6. Fréedericksz V, Repiewa AZ. Phys Soc. 1927;42:532–46. doi:10.1007/BF01397711.

    Google Scholar 

  7. Goodby JW. The nanoscale engineering of nematic liquid crystals for displays. Liq Cryst. 2011;38:1363–87.

    Article  CAS  Google Scholar 

  8. Baughman RH, Zakhidov AA, de Heer WA. Carbon nanotubes—the route toward applications. Science. 2002;297:787–92.

    Article  CAS  Google Scholar 

  9. Tans SJ, Verschueren ARM, Dekker C. Room-temperature transistor based on a single carbon nanotube. Nature. 1998;393:49–52.

    Article  CAS  Google Scholar 

  10. Collins PG, Avouris P. Nanotubes for electronics. Sci Am. 2000;283:62–9.

    Article  CAS  Google Scholar 

  11. de Heer WA, Chátelian A, Ugarte D. A carbon nanotube field-emission electron source. Science. 1995;270:1179–80.

    Article  Google Scholar 

  12. Kumar S. Functional discotic liquid crystals. Isr J Chem. 2012;52:820–9.

    Article  CAS  Google Scholar 

  13. Malthéte J, Nguyen HT, Destrade C. Phasmids and polycatenar liquid crystals. Liq Cryst. 1993;13:171–87.

    Article  Google Scholar 

  14. Niori T, Sekine T, Watanabe J. Distinct ferroelectric smectic liquid crystals consisting of banana shaped achiral molecules. J Mater Chem. 1996;6:1231–3.

    Article  CAS  Google Scholar 

  15. Kato T, Mizoshita N, Kishimoto K. Functional liquid-crystalline assemblies: self-organized soft materials. Angew Chem Int Ed. 2006;45:38–68.

    Article  CAS  Google Scholar 

  16. Kato T, Fréchet JMJ. A new approach to mesophase stabilization through hydrogen bonding molecular interactions in binary mixtures. J Am Chem Soc. 1989;111:8533–4.

    Article  CAS  Google Scholar 

  17. Paleos CM, Tsiourvas D. Supramolecular hydrogen-bonded liquid crystals. Liq Cryst. 2001;28:1127–61.

    Article  CAS  Google Scholar 

  18. Kato T, Mizoshita N, Kanie K. Hydrogen-bonded liquid crystalline materials: supramolecular polymeric assembly and the induction of dynamic function. Macromol Rapid Commun. 2001;22:797–814.

    Article  CAS  Google Scholar 

  19. Srinivasulu M, Satyanarayana PVV, Kumar PA, Pisipati VGKM. Induced smectic-G phase through intermolecular hydrogen bonding part VIII: phase and crystallization behaviours of 2-(p-n-heptyloxybenzyIidene imino)-5-chIoro-pyridine: p-n-alkoxybenzoic acid (HICP:n ABA) complexes. Z Naturforsch. 2001;56a:685–91.

    Google Scholar 

  20. Barmatov EB, Barmatova MV. Induction of the chiral nematic phase in hydrogen-bonded blends of smectic copolymers and low molar mass dopant. Liq Cryst. 2003;30:1075–8.

    Article  CAS  Google Scholar 

  21. Wei Q, Shi L, Yuan X, Zhang L, Cao H, Yang H. Synthesis and phase behaviour of hydrogen-bonded liquid crystalline complexes of allyloxybenzoic acid compounds with 4,4′-bipyridine. Liq Cryst. 2007;34:855–60.

    Article  CAS  Google Scholar 

  22. Kohmoto S, Someya Y, Kishikawa K. Liquid crystalline molecules with hydrogen-bonding networks in the direction of molecular short axes. Liq Cryst. 2010;37:209–16.

    Article  CAS  Google Scholar 

  23. Vijayakumar VN, Madhu Mohan MLN. Study of optical shutter in cholesteric phase of a double hydrogen bonded ferroelectric liquid crystal with two chiral carbons. Mol Cryst Liq Cryst. 2010;528:163–7.

    Article  CAS  Google Scholar 

  24. Kato T, Adachi H, Fujishima A, Fréchet JMJ. Self-assembly of liquid crystalline complexes having angular structures through intermolecular hydrogen bonding. Chem Lett. 1992;21:265–8.

    Article  Google Scholar 

  25. Kato T, Fujishima A, Fréchet JMJ. Self-assembly of a twin liquid crystalline complex through intermolecular hydrogen bondings. Chem Lett. 1990;19:919–22.

    Article  Google Scholar 

  26. Vorländer D. About transparently clear, crystalline liquids. Verh Dtsch Chem Ges. 1908;41:2033–52.

    Article  Google Scholar 

  27. Mallia VA, Antharjanam PKS, Das S. Synthesis and studies of some 4-substituted phenyl-4′-azopyridine-containing hydrogen-bonded supramolecular mesogens. Liq Cryst. 2003;30:135–41.

    Article  CAS  Google Scholar 

  28. Parra M, Hidalgo P, Barbera J, Alderete J. Properties of thermotropic liquid crystals induced by hydrogen bonding between pyridyl-1,2,4-oxadiazole derivatives and benzoic acid, 4-chlorobenzoic acid or 4-methylbenzoic acid. Liq Cryst. 2005;32:573–7.

    Article  CAS  Google Scholar 

  29. Naoum MM, Fahmi AA, Alaasar MA. Supramolecular hydrogen-bonded liquid crystals formed from 4-(4′-pyridylazophenyl)-4″-substituted benzoates and 4-alkoxybenzoic acids. Mol Cryst Liq Cryst. 2008;482:57–70.

    Article  CAS  Google Scholar 

  30. Naoum MM, Fahmi AA, Alaasar MA. Supramolecular hydrogen-bonded liquid crystals formed from 4-(4′-pyridylazophenyl)-4″-alkoxy benzoates and 4-substituted benzoic acids. Mol Cryst Liq Cryst. 2008;487:74–91.

    Article  CAS  Google Scholar 

  31. Naoum MM, Fahmi AA, Alaasar MA. Supramolecular liquid crystals induced by hydrogen-bonding interactions between non-mesomorphic compounds. I. 4-(4′-Pyridylazophenyl)-4″-substituted benzoates and 4-substituted benzoic acids. Mol Cryst Liq Cryst. 2009;506:22–33.

    Article  CAS  Google Scholar 

  32. Bhagavath P, Bhat SG, Mahabaleshwara S, Girish SR, Potukuchi DM, Srinivasulu M. Induced Smectic-A phase at low temperatures through self-assembly. J Mol Struct. 2013;1039:94–100.

    Article  CAS  Google Scholar 

  33. Bhagavath P, Mahabaleshwara S, Bhat SG, Potukuchi DM, Pallavajhula VC, Srinivasulu M. Thermal stabilities in supramolecular liquid crystals: Influence of the size and position of a substituent. J Mol Liq. 2013;186C:56–62.

    Article  Google Scholar 

  34. Kumar PA, Srinivasulu M, Pisipati VGKM. Induced smectic G phase through intermolecular hydrogen bonding. Liq Cryst. 1999;26:1339–43.

    Article  CAS  Google Scholar 

  35. Alshahateet SF. Synthesis and supramolecularity of hydrogen-bonded cocrystals of pharmaceutical model rac-ibuprofen with pyridine derivatives. Mol Cryst Liq Cryst. 2010;533(1):152–161 and the references therein.

  36. Naoum MM, Saad G, Nessim R, Seliger H. Effect of molecular structure on the phase behavior of some liquid crystalline compounds and their binary mixtures II. 4-Hexadecyloxyphenyl arylates and aryl 4-hexadecyloxy benzoates. Liq Cryst. 1997;23:789–95.

    Article  CAS  Google Scholar 

  37. Bhat SG, Srinivasulu M, Girish SR, Padmalatha, Bhagavath P, Mahabaleshwara S, Potukuchi DM, Muniprasad M. Influence of moieties and chain length on the abundance of orthogonal and tilted phases of linear hydrogen-bonded liquid crystals, Py16BA:nOBAs. Mol Cryst Liq Cryst. 2012;552(1):83–96.

    Article  CAS  Google Scholar 

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Acknowledgements

I acknowledge the management of Manipal University, Manipal, for providing the laboratory facilities. I extend my sincere thanks to Dr. M. Srinivasulu, for his guidance in accomplishing this work.

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Authors and Affiliations

  1. Department of Chemistry, Manipal Institute of Technology, Manipal University, Manipal, 576 104, India

    Poornima Bhagavath

  2. Syngene International Ltd., Biocon Park, Bommasandra, Bengaluru, 560 099, India

    S. Mahabaleshwara

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  1. Poornima Bhagavath
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  2. S. Mahabaleshwara
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Correspondence to Poornima Bhagavath.

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Bhagavath, P., Mahabaleshwara, S. Mesomorphism in binary mixtures of 4-((hexylimino)methyl)benzoic acid and 4-alkyloxybenzoic acids. J Therm Anal Calorim 129, 339–345 (2017). https://doi.org/10.1007/s10973-017-6105-y

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