Abstract
A series of fluorinated benzoic acid–pyridine supramolecular liquid crystals and their non-fluorinated analogues were synthesized and studied by use of polarizing optical microscopy (POM), differential scanning calorimetry, and X-ray diffraction. A smectic phase was identified for the fluorine-bearing products, with high clear points, and two peaks (2θ ≈ 6.5°, 24°) in X-ray diffraction. However, non-fluorinated analogues have a nematic phase with low clear points and one peak (2θ ≈ 23°) in X-ray diffraction. This indicates that one trifluoromethyl is able to increase stability and the degree of order of hydrogen-bonded supramolecular liquid crystals.
Graphical Abstract
.
Similar content being viewed by others
References
Gray GW, Demus D, Spiess HW, Goodby JW, Vill V (1998) Handbook of liquid crystals. Wiley–VCH, Weinheim
Gray GW (1987) Thermotropic liquid crystals. Wiley, Chichester
Collings PJ, Hird M (1997) Introduction to liquid crystals. Taylor & Francis, London
Richard JB, Ken K (2011) Liq Cryst 38:1415
Ian S (2011) Liq Cryst 38:1551
Achalkumar AS, Yelamaggad CV (2012) Tetrahedron Lett 53:7108
Shilpa S, Sumyra S, Santanu KP (2012) Tetrahedron Lett 53:6446
Constantinos MP, Dimitris T (2001) Liq Cryst 28:1127
Kanie K, Nishii M, Yasuda T, Taki T, Ujiie S, Kato T (2001) J Mater Chem 11:2875
Kato T, Matsuoka T, Nishii M, Kamikawa Y, Kanie K, Nishimura T, Yashima E, Vjiie S (2004) Angew Chem Int Ed 43:1969
Lehn JM (2002) Science 295:2400
Prins LJ, Reinhoudt DN, Timmerman P (2001) Angew Chem Int Ed 40:2382
Stubbs LP, Week M (2003) J Eur Chem 9:992
Pollino JM, Nair KP, Stubbs LP, Adams J, Week M (2004) Tetrahedron 60:7205
Archer EA, Gong H, Krische MJ (2001) Tetrahedron 57:1139
Chino K, Ashiura M (2001) Macromolecules 34:9201
Kato T (2000) Struct Bonding 96:95
Michael H (2007) Chem Soc Rev 36:2070
Fornasieri G, Guittard F, Geribaldi S (2003) Liq Cryst 30:663
Kato T, Kihara H, Uryu T, Fujishima A, Frechet JM (1992) Macromolecules 25:6836
Lee CM, Jariwala CP, Griffin AC (1994) Polymer 35:4550
Pourcain CBS, Griffin AC (1995) Macromolecules 28:4116
Michael H, Enneth JT (1998) Mol Cryst Liq Cryst 323:1
Frederic G, Elisabeth TG, Serge G, Aime C (1999) J Fluorine Chem 100:85
Acknowledgments
Financial support from the Shandong Excellent Young Scientist Research Award Fund (Project No. BS2011CL007) is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Liu, Z., Han, J., Zhang, J. et al. Synthesis and mesomorphic properties of new fluorinated hydrogen-bonded supramolecular liquid crystals. Monatsh Chem 145, 71–77 (2014). https://doi.org/10.1007/s00706-013-1021-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-013-1021-8