Issue 23, 2013
From the journal:

Journal of Materials Chemistry C

Elucidating the smectic A-promoting effect of halogen end-groups in calamitic liquid crystals†

Ian Rupar,a   Kirk M. Mulligan,a   Jeffrey C. Roberts,a   Dorothee Nonnenmacher,b   Frank Giesselmannb  and  Robert P. Lemieux*a  

* Corresponding authors

a Chemistry Department, Queen's University, Kingston, Ontario, Canada
E-mail: lemieux@chem.queensu.ca

b Institute of Physical Chemistry, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany

Abstract

Two isometric series of chloro-terminated 5-alkoxy-2-(4-alkoxyphenyl)pyrimidine mesogens QL8-m/n and QL9-m/n (m + n = 16), with the chloro-terminated alkoxy chain tethered to either the pyrimidine ring or the phenyl ring, were synthesized and their liquid crystalline properties characterized by polarized optical microscopy and differential scanning calorimetry. Based on the analysis of mesogenic properties and correlations to electrostatic potential isosurfaces calculated at the B3LYP/6-31G* level, we present evidence suggesting that the SmA-promoting effect of chloro end-groups is not due to strong polar interactions at the layer interfaces, as previously postulated in the literature. Instead, the evidence suggests that the SmA-promoting effect is due to the electron-withdrawing effect of the chloro end-group, which should reduce electrostatic repulsion between alkoxy chains and, consequently, increase van der Waals interactions between aromatic cores in the orthogonal SmA phase.

Graphical abstract: Elucidating the smectic A-promoting effect of halogen end-groups in calamitic liquid crystals

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Article information

DOI
https://doi.org/10.1039/C3TC30534A
Article type
Paper
Submitted
21 Mar 2013
Accepted
02 May 2013
First published
03 May 2013

J. Mater. Chem. C, 2013,1, 3729-3735

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Elucidating the smectic A-promoting effect of halogen end-groups in calamitic liquid crystals

I. Rupar, K. M. Mulligan, J. C. Roberts, D. Nonnenmacher, F. Giesselmann and R. P. Lemieux, J. Mater. Chem. C, 2013, 1, 3729 DOI: 10.1039/C3TC30534A

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