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RESEARCH ARTICLE
Contents Vol 67(7)

Cyanobiphenyl versus Alkoxybiphenyl: Which Mesogenic Unit Governs the Mesomorphic Properties of Guanidinium Ionic Liquid Crystals?

Johannes Christian Haenle A , Manuel M. Neidhardt A , Stuart Beardsworth A , Jochen Kirres A , Angelika Baro A and Sabine Laschat A B
+ Author Affiliations
- Author Affiliations

A Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany.

B Corresponding author. Email: sabine.laschat@oc.uni-stuttgart.de

Australian Journal of Chemistry 67(7) 1088-1099 https://doi.org/10.1071/CH14376
Submitted: 28 March 2014  Accepted: 11 June 2014   Published: 30 June 2014

Abstract

A series of phenylguanidinium salts 3·X, which are linked via an alkoxy spacer either to a 4-decyloxy- or 4-cyano-substituted biphenyl mesogen, was prepared and the mesomorphism studied. A decyloxybiphenyl core and a spacer of at least C6 chain length were required for mesophase formation. Replacement of the chloride counterion by other anions like bromide or tetrafluoroborate improved the thermal stability of the mesophase. A comparison of substitution pattern (meta v. para) on the phenyl ring revealed decreased melting and clearing points for the bent cationic head group. All guanidinium ionic liquid crystals 3 displayed only smectic A (SmA) phases. A packing model is assumed where the molecules in a bilayer stack over each other in opposite direction with interdigitated terminal decyloxy groups and spacers.


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