Skip to main content
Log in

Mesomorphic behavior of methanesulfonate salts of esters of L-Methionine and their optical properties

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

A set of methanesulfonate salts of esters of (S)-2-Amino-4-(methylthio)butanoic acid [L-Methionine] and fatty alcohols have been synthesized in good yields by a green protocol involving a one-step and solvent-free approach. All derivatives have been evaluated for their liquid crystalline properties using polarizing optical microscopy and differential scanning calorimetry and found to be enantiotropic liquid crystals. Refractive indices were measured for one of the derivatives at different temperatures and wavelengths. It exhibited a high Abbe number and low dispersive power.

Graphic Abstract 

Synopsis: To be provided by author

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. Pelzl G and Hauser A 1991 Birefringence and phase transitions in liquid crystals Phase Trans. 37 33

    Article  CAS  Google Scholar 

  3. Tschierske C 2013 Development of structural complexity by liquid-crystal self-assembly Angew. Chem. Int. Ed.  52 8828

    Article  CAS  Google Scholar 

  4. Binnemans K 2005 Ionic liquid crystals Chem. Rev.  105 4148

    Article  CAS  Google Scholar 

  5. Paleos C M 1994 Thermotropic liquid crystals derived from amphiphilic mesogens Mol. Cryst. Liq. Cryst. 243 159

    Article  CAS  Google Scholar 

  6. Kouwer P J and Fernandez A 2016 Key developments in ionic liquid crystals Int. J. Mol. Sci.  17 731

    Article  Google Scholar 

  7. Ujiie S and Iimura K 1992 Thermal properties and orientational behavior of a liquid crystalline-ion complex polymer Macromol.  25 3174

    Article  CAS  Google Scholar 

  8. Do T D and Schmitzer A R 2015 Intramolecular Diels Alder reactions in highly organized imidazolium salt-based ionic liquid crystals RSC Adv.  5 635

    Article  CAS  Google Scholar 

  9. Amann T, Dold C and Kailer A 2012 Rheological characterization of ionic liquids and ionic liquid crystals with promising tribological performance Soft Matter  8 9840

    Article  CAS  Google Scholar 

  10. Faul C J F 2014 Ionic Self-assembly for functional hierarchical nanostructured materials Acc. Chem. Res.  47 3428

    Article  CAS  Google Scholar 

  11. Santella M, Amini F, Andreasen K B, Aswad D S, Ausar H, Austin, L M, Bora I, Boye I M I, Brinkenfeldt N K and Bøe M F 2015 Template-guided ionic self-assembled molecular materials and thin films with nanoscopic order Chem. Nano. Mat.  1 253

    CAS  Google Scholar 

  12. Chi W S, Jeon H, Kim S J, Kim D J and Kim J H 2013 Ionic liquid crystals: synthesis, structure and applications to \({\rm I}_{2}\)-free solid-state dye-sensitized solar cells Macromol. Res.  21 315

    Article  CAS  Google Scholar 

  13. Devaki S J and Sasi R 2017 Ionic liquids/ionic liquid crystals for safe and sustainable energy storage systems In Progress and Developments in Ionic liquids Scott Handy (Ed.) (UK: InTechOpen)

    Google Scholar 

  14. Woltman S J, Jay G D and Crawford G P 2007 Liquid-crystal materials find new order in biomedical applications Nat. Mater.  6 929

    Article  CAS  Google Scholar 

  15. Binnemans K, Goossens K, Lava K and Bielawsk C W 2016 Ionic liquid crystals: versatile materials Chem. Rev.  116 4643

    Article  Google Scholar 

  16. Echue G, Llyod-Jones G and Faul C F J 2015 Chiral perylene diimides: building blocks for ionic self-assembly Chem. Eur. J.  21 5118

    Article  CAS  Google Scholar 

  17. Axenov K V and Laschat S 2011 Thermotropic ionic liquid crystals Materials  4 206

    Article  CAS  Google Scholar 

  18. Neidhardt M M, Wolfrum W, Breadsworth S, Wohrle T, Frey W, Baro A, Stubenrauch C, Giesselmann F and Laschat S 2016 Tyrosine-based ionic liquid crystals: switching from a smectic A Chem. Eur. J. 22 1

    Article  Google Scholar 

  19. Neidhardt M, Schmitt K, Baro A, Schneider C, Bilitewski U and Laschat S 2018 Self-assembly and biological activities of ionic liquid crystals derived from aromatc amino acids Phys. Chem. Chem. Phys.  20 20371

    Article  CAS  Google Scholar 

  20. Kulkarni P 2015 Methane sulphonic acid is green catalyst in organic synthesis Orient. J. Chem.  31 447

    Article  Google Scholar 

  21. Chen B, Fang J, Wu J, Huang W, Wang J and Zhang N 2013 The influence of amino acids on biodegradability, oxidation stability, and corrosiveness of lubricating oil J. Pet. Sci. Technol.  31 185

    Article  CAS  Google Scholar 

  22. UK/ICCA “SIDS Initial Assessment Profile” 2006 OECD Existing Chemicals Database

  23. Yang M, Stappert K and Mudring A 2014 Bis-cationic ionic liquid crystals J. Mater. Chem.  2 458

    CAS  Google Scholar 

  24. Govindaiah T N 2016 Electro-optical and thermodynamic studies on induced reentrant smectic-a phase in binary mixture of liquid crystalline materials Chem. Technol. Ind. J.  11 106

    Google Scholar 

  25. Demus D and Richter L 1978 Textures of Liquid Crystals (Berlin: Verlag Chemie)

  26. Li J 2005 Refractive Indices of Liquid Crystals and their Applications in Display and Photonic Devices Electronic Theses and Dissertations 4460

  27. Jessy P J, Radha S and Patel N 2018 Morphological, optical and dielectric behavior of chiral nematic liquid crystal mixture: study on effect of different amount of chirality J. Mol. Liq.  255 215

    Article  CAS  Google Scholar 

  28. Jessy P J, Radha S and Patel N 2018 Highly improved dielectric behaviour of ferronematic nanocomposite for display application Liq. Cryst.  46 772

    Google Scholar 

  29. Suzuki Y, Higashihara T, Ando S and Ueda M 2012 Synthesis and characterization of high refractive index and high Abbe’s number poly(thioether sulfone)s based on Tricyclo [5.2.1.0\(^{2,6}\)]decane moiety Macromol. 45 3402

  30. Ren H, Fox D W, Wu B and Wu S 2007 Liquid crystal lens with large focal length tunability and low operating voltage Optic Express  15 11328

    Article  CAS  Google Scholar 

  31. Lin Y, Wang Y and Reshetnyak V 2017 Liquid crystal lenses with tunable focal length Liq. Cryst. Rev.  5 111

    Article  CAS  Google Scholar 

  32. Lin Y, Chen H and Chen M 2014 Electrically tunable liquid crystal lenses and applications Mol. Cryst. Liq. Cryst.  596 12

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank the Department of Chemistry, University of Mumbai for financial support and facilities. Sheetal Venkatesh and Pushpa Kumari Yadav also thank UGC, New Delhi for the UGC Non-NET Ph. D Research fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M M V Ramana.

Ethics declarations

Conflict of interest

There are no conflicts of interest to declare.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (pdf 1069 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Venkatesh, S., Yadav, P.K. & Ramana, M.M.V. Mesomorphic behavior of methanesulfonate salts of esters of L-Methionine and their optical properties. J Chem Sci 131, 65 (2019). https://doi.org/10.1007/s12039-019-1644-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-019-1644-3

Keywords

Navigation