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2012 | OriginalPaper | Buchkapitel

Fluorinated Liquid Crystals: Design of Soft Nanostructures and Increased Complexity of Self-Assembly by Perfluorinated Segments

verfasst von : Carsten Tschierske

Erschienen in: Liquid Crystals

Verlag: Springer Berlin Heidelberg

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Abstract

The effects of perfluorinated and semiperfluorinated hydrocarbon units on the self-assembly of rod-like, disc-like, polycatenar, taper- and star-shaped, dendritic, and bent-core liquid crystalline (LC) materials is reviewed. The influence of fluorinated segments is analyzed on the basis of their contributions to the cohesive energy density, molecular shape, conformational flexibility, micro-segregation, space filling, and interface curvature. Though the focus is on recent progress in the last decade, previous main contributions, general aspects of perfluorinated organic molecules, and the basics of LC self-assembly are also briefly discussed to provide a complete overall picture. The main focus is on structure-property-relations and the use of micro-segregation to tailor mesophase morphologies. Especially polyphilic molecules with perfluorinated segments provide new modes of LC self-assembly, leading to ordered fluids with periodic multi-compartment structures and enhanced complexity compared to previously known systems.

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Nächstes Kapitel Liquid Crystalline Crown Ethers
Fußnoten
1
More detailed analysis is possible with the Hansen solubility parameters where the total solubility parameter (δ t), which corresponds to the Hildebrand parameter (δ) is split into contributions by dispersion (δ d), dipolar interactions (δ p) and hydrogen bonding (δ h) [28].; for complex molecules the solubility parameters can be estimated from segmental group contributions. Estimation of the incompatibility of segments in LC molecules is also possible by means of the Flory interaction parameter χ = (δ A − δ Β)2 V r(RT)-1 (V r = relative volume = average volume of the repeat units), used for polymer solutions and allows direct the calculation of the Gibbs free energy. χN (N = number of repeat units, related to the size of the molecule) expresses the enthalpy-entropy balance and the larger the value, the stronger the segregation [23]. The disadvantages of these estimations are that they refer only to room temperature and do not consider the rigid flexible incompatibility, which is present in most LC molecules (rod-like, disc-like).
 
2
Common cubic space groups in thermotropic LC systems: CubV: Ia3d, Im3m (Pn3m); CubI: Pm3n, Im3m.
 
3
Phase transitions can also take place depending on the concentration of a solvent [37, 38]. These lyotropic phases will not be considered here.
 
4
This should not be mixed up with the existence range of a mesophase which also depends on the stability of an adjacent crystalline or other LC phases.
 
5
However, this is mainly due to the relatively strong dipole moment provided by the CH2-CF3 linkage.
 
6
If the boiling points are correlated with the molecular volumes the difference appears much smaller.
 
7
The CED (c) is directly related to the vaporization enthalpy by the equation: c = (ΔH V-RT)/V m, (V m = molecular volume); ΔH V is related to the boiling point.
 
8
In fact the boiling points of the perfluoroalkanes are only about 25-30 K higher than those of noble gases with similar molecular mass, i.e. the CEDs of perfluoroalkanes are comparable with gases and hence gases have a high solubility in perfluoroalkanes.
 
9
As the main contribution to polarizability comes from the carbon frame and the dispersion interactions strongly decrease with the distance, the contribution of this interaction should be larger for RF-RH interaction which allows shorter distances between the carbon frames than RF-RF interaction. Related arguments were used to explain the attractive interactions between aromatic hydrocarbons and aromatic fluorocarbons allowing a short 3.5 nm face-to-face distance (see Sect. 10.1). However, there are also electrostatic interactions between the partial charges (C(-)-H(+) and C(+)-F(-)) where interactions between the charges of peripheral atoms of one molecule and the carbon frame of the other provide a destabilizing contribution to the interaction between RF and RH chains [78].
 
10
Hence, benzoic acids can be more appropriately considered as self-assembled rod-like mesogens with two fluorinated terminal chains (see Sect. 4.4).
 
11
Strongly enhanced melting temperatures can hide LC phases in some cases.
 
12
As the cross sectional area of the mixed RH and RF chains is still larger than that of the aromatic cores random tilt (de Vries-like SmA) or uniform tilt (SmC) can compensate this remaining mismatch.
 
13
The mesophase stabilization by the fluorophobic effect is remarkably large for compound 176a (Colrec/p2mg 144 °C SmA 174 °C Iso) [295] and compound 176b: Colrec/p2mg 88 °C SmA 167 ° Iso [299] if compared to the related non-fluorinated compound (Colortho 53 °C Iso) [295]; (Fig. 47).
 
14
Besides the T-shaped bolaamphiphiles covered here, there are also T-shaped polyphiles with a reversed position of hydrophilic and lipophilic units, see [311‐313].
 
15
See also Footnote 9 (Sect. 1.3) for an alternative discussion of the origin of attractive interactions between fluorinated and non-fluorinated aromatics.
 
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Metadaten
Titel
Fluorinated Liquid Crystals: Design of Soft Nanostructures and Increased Complexity of Self-Assembly by Perfluorinated Segments
verfasst von
Carsten Tschierske
Copyright-Jahr
2012
Verlag
Springer Berlin Heidelberg
Buch
Liquid Crystals

Print ISBN: 978-3-642-27590-6

Electronic ISBN: 978-3-642-27591-3

Copyright-Jahr: 2012

DOI
https://doi.org/10.1007/128_2011_267

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