Co-reporter:Daniel A. Paterson; Jie Xiang; Gautam Singh; Rebecca Walker; Deña M. Agra-Kooijman; Alfonso Martı́nez-Felipe; Min Gao; John M. D. Storey; Satyendra Kumar; Oleg D. Lavrentovich
Journal of the American Chemical Society 2016 Volume 138(Issue 16) pp:5283-5289
Publication Date(Web):March 25, 2016
DOI:10.1021/jacs.5b13331
The liquid crystal nonsymmetric dimer, 1-(4-butoxyazobenzene-4′-yloxy)-6-(4-cyanobiphenyl-4′-yl) hexane (CB6OABOBu), shows enantiotropic twist–bend nematic, NTB, and nematic, N, phases. The NTB phase has been confirmed using polarized light microscopy, freeze fracture transmission electron microscopy, and X-ray diffraction. The helicoidal pitch in the NTB phase is 18 nm. The NTB–N (TNTBN) and N–I (TNI) transition temperatures are reduced upon UV light irradiation, with the reduction in TNTBN being much larger than that in TNI. An isothermal, reversible NTB–N transition may be driven photochemically. These observations are attributed to a trans–cis photoisomerization of the azobenzene fragment on UV irradiation, with the cis isomers stabilizing the standard nematic phase and the trans isomers stabilizing the NTB phase. The dramatic changes in TNTBN provide evidence that the transition between the normal nematic and twist–bend nematic with spontaneous breaking of chiral symmetry is crucially dependent on the shape of molecular dimers, which changes greatly during the trans–cis isomerization.
Co-reporter:Daniel A. Paterson, Min Gao, Young-Ki Kim, Afsoon Jamali, Kirsten L. Finley, Beatriz Robles-Hernández, Sergio Diez-Berart, Josep Salud, M. Rosario de la Fuente, Bakir A. Timimi, Herbert Zimmermann, Cristina Greco, Alberta Ferrarini, John M. D. Storey, David O. López, Oleg D. Lavrentovich, Geoffrey R. Luckhurst and Corrie T. Imrie
Soft Matter 2016 vol. 12(Issue 32) pp:6827-6840
Publication Date(Web):11 Jul 2016
DOI:10.1039/C6SM00537C
The synthesis and characterisation of the nonsymmetric liquid crystal dimer, 1-(4-cyanobiphenyl-4′-yloxy)-6-(4-cyanobiphenyl-4′-yl)hexane (CB6OCB) is reported. An enantiotropic nematic (N)–twist-bend nematic (NTB) phase transition is observed at 109 °C and a nematic–isotropic phase transition at 153 °C. The NTB phase assignment has been confirmed using polarised light microscopy, freeze fracture transmission electron microscopy (FFTEM), 2H-NMR spectroscopy, and X-ray diffraction. The effective molecular length in both the NTB and N phases indicates a locally intercalated arrangement of the molecules, and the helicoidal pitch length in the NTB phase is estimated to be 8.9 nm. The surface anchoring properties of CB6OCB on a number of aligning layers is reported. A Landau model is applied to describe high-resolution heat capacity measurements in the vicinity of the NTB–N phase transition. Both the theory and heat capacity measurements agree with a very weak first-order phase transition. A complementary extended molecular field theory was found to be in suggestive accord with the 2H-NMR studies of CB6OCB-d2, and those already known for CB7CB-d4. These include the reduced transition temperature, TNTBN/TNI, the order parameter of the mesogenic arms in the N phase close to the NTB–N transition, and the order parameter with respect to the helix axis which is related to the conical angle for the NTB phase.
Co-reporter:Suzanne M. Jansze;Dr. Alfonso Martínez-Felipe; John M. D. Storey;Dr. Antonius T. M. Marcelis; Corrie T. Imrie
Angewandte Chemie 2015 Volume 127( Issue 2) pp:653-656
Publication Date(Web):
DOI:10.1002/ange.201409738
Abstract
The liquid crystalline phase behavior of 4-[6-(4′-cyanobiphenyl-4-yl)hexyloxy]benzoic acid (CB6OBA) and 4-[5-(4′-cyanobiphenyl-4-yloxy)pentyloxy]benzoic acid (CBO5OBA) is described. Both acids show an enantiotropic nematic phase attributed to the formation of supramolecular complexes by hydrogen bonding between the benzoic acid units. In addition, CB6OBA provides the first example of hydrogen bonding driving the formation of the twist-bend nematic phase. The observation of the twist-bend nematic phase for CB6OBA, but not CBO5OBA, is attributed to the more bent molecular shape of the complexes formed by the former, reinforcing the view that shape is a key factor in stabilizing this new phase. Temperature-dependent FTIR spectroscopy reveals differences in hydrogen bonding between the two nematic phases shown by CB6OBA which suggest that the open hydrogen-bonded complexes may play an important role in stabilizing the helical arrangement found in the twist-bend nematic phase.
Co-reporter:Suzanne M. Jansze;Dr. Alfonso Martínez-Felipe; John M. D. Storey;Dr. Antonius T. M. Marcelis; Corrie T. Imrie
Angewandte Chemie International Edition 2015 Volume 54( Issue 2) pp:643-646
Publication Date(Web):
DOI:10.1002/anie.201409738
Abstract
The liquid crystalline phase behavior of 4-[6-(4′-cyanobiphenyl-4-yl)hexyloxy]benzoic acid (CB6OBA) and 4-[5-(4′-cyanobiphenyl-4-yloxy)pentyloxy]benzoic acid (CBO5OBA) is described. Both acids show an enantiotropic nematic phase attributed to the formation of supramolecular complexes by hydrogen bonding between the benzoic acid units. In addition, CB6OBA provides the first example of hydrogen bonding driving the formation of the twist-bend nematic phase. The observation of the twist-bend nematic phase for CB6OBA, but not CBO5OBA, is attributed to the more bent molecular shape of the complexes formed by the former, reinforcing the view that shape is a key factor in stabilizing this new phase. Temperature-dependent FTIR spectroscopy reveals differences in hydrogen bonding between the two nematic phases shown by CB6OBA which suggest that the open hydrogen-bonded complexes may play an important role in stabilizing the helical arrangement found in the twist-bend nematic phase.
Co-reporter:Andrew G. Cook, Rachel T. Inkster, Alfonso Martinez-Felipe, Amparo Ribes-Greus, Ian W. Hamley, Corrie T. Imrie
European Polymer Journal 2012 Volume 48(Issue 4) pp:821-829
Publication Date(Web):April 2012
DOI:10.1016/j.eurpolymj.2012.01.021
The homologous series of side chain liquid crystal polymers, the poly[ω-(4-methoxyazobenzene-4′-oxy)alkyl methacrylate]s, has been prepared in which the length of the flexible alkyl spacer has been varied from 3 to 11 methylene units. All the polymers exhibit liquid crystalline behaviour. The propyl and butyl members show exclusively nematic behaviour. The pentyl, hexyl, octyl and decyl members show a nematic and a smectic A phase while the heptyl, nonyl and undecyl homologues exhibit only a smectic A phase. The smectic A phase has been studied using X-ray diffraction and assigned as a smectic A1 phase in which the side chains are fully overlapped and the backbones are confined to lie between the smectic layers. For the nonyl member an incommensurate smectic phase is observed. The dependence of the transition temperatures on the length of the flexible spacer is understood in terms of the average shapes of the side chains.Graphical abstractHighlights► Report the phase behaviour of a homologous series of photo sensitive SCLCPs. ► Increasing spacer length promotes smectic behaviour relative to nematic behaviour. ► A fully interleaved smectic A1 phase is seen with incommensurate smectic behaviour. ► Smectic phase formation is driven by packing efficiency. ► Transition temperatures interpreted in terms of the average shape of the side chains.
Co-reporter:Toby Donaldson, Peter A. Henderson, Marie France Achard and Corrie T. Imrie
Journal of Materials Chemistry A 2011 vol. 21(Issue 29) pp:10935-10941
Publication Date(Web):06 Jun 2011
DOI:10.1039/C1JM10992H
The synthesis and characterisation of two new series of liquid crystal tetramers in which four mesogenic groups are linked via three alkyl spacers is reported. In each series the length of the outer two spacers, n, is varied between 3, 4, 5, 7, 10 and 11 methylene units while the central spacer length, m, is either 5 or 6 methylene units. The outer two mesogenic groups are cholesteryl-based, Chol, while the inner two are Schiff's bases, SB. The tetramers are referred to by the acronym Chol-n-SB-m-SB-n-Chol. All twelve tetramers exhibit an enantiotropic chiral nematic phase. The chiral nematic-isotropic transition temperatures and associated entropy changes depend critically on the combination of spacers in the tetramer and this is interpreted in terms of average molecular shapes. The tetramers with m = 5 and n = 5, 7, and m = 6 and n = 3, 4, 5, 7, show a monolayer chiral smectic C* phase, the driving force for which may be the mismatch in the cross-sectional areas of the differing mesogenic groups. The tetramers with m=6 and n = 10, 11 show a quadruply intercalated smectic A phase characterised by a smectic periodicity to estimated molecular length ratio of just 0.23. The driving force for the formation of this phase is thought to be specific electrostatic interactions between the unlike mesogenic units while the formation of the phase is strongly dependent on the length and parity of the spacers due to packing constraints. On cooling, a new phase transition is seen, possibly driven by conformational changes in the outer flexible spacers, for both these tetramers from the intercalated smectic A phase to an intercalated alternating chiral smectic C* phase in which the layers consist of either the mixed mesogenic groups or solely the cholesteryl-based moieties.
Co-reporter:Andrew G. Cook, James L. Wardell, Corrie T. Imrie
Chemistry and Physics of Lipids 2011 Volume 164(Issue 2) pp:118-124
Publication Date(Web):February 2011
DOI:10.1016/j.chemphyslip.2010.11.007
Seven members of the methyl-6-O-(n-acyl)-α-d-glucopyranosides have been synthesised and their transitional properties determined. The undecanoyl and octadecanoyl members do not exhibit liquid crystallinity while the members having chain lengths between dodecanoyl and hexadecanoyl exhibit a monotropic smectic A phase. Variable temperature infrared spectroscopy reveals that the hydrogen bonding within the system shows a marked change at the melting point but apparently no change at the smectic A-isotropic transition. This observation is interpreted in terms of Goodby's model for the smectic A phase in which the carbohydrate moieties are located at the centre of the smectic bilayer and assuming that hydrogen bonded aggregates persist into the isotropic phase. Within this framework, the unusually low values of the entropy change associated with the smectic A-isotropic transition may also be accounted for.
Co-reporter:Corrie T. Imrie and Peter A. Henderson
Chemical Society Reviews 2007 vol. 36(Issue 12) pp:2096-2124
Publication Date(Web):17 Oct 2007
DOI:10.1039/B714102E
The underlying theme of this Critical Review is the relationship between molecular structure and liquid crystalline behaviour in a class of materials referred to as liquid crystal oligomers. For the purposes of this review, a liquid crystal oligomer will be defined as consisting of molecules composed of semi-rigid mesogenic units connected via flexible spacers. Much of the review will be devoted to structure–property relationships in the simplest oligomers, namely dimers, in which just two mesogenic units are connected by a single spacer. Along the way we will see how this molecular architecture has been exploited to address issues in a range of quite different areas and has given rise to potential applications for these materials. On the whole, only compounds in which the mesogenic units are linked essentially in a linear fashion will be considered while structures such as liquid crystal dendrimers and tetrapodes fall outside the scope of this review. The review will be of interest not only to scientists working directly in this area but in particular to those interested in understanding the relationships between structure and properties in polymers, and those designing materials for new applications (231 references).
Co-reporter:Corrie T. Imrie, Zhibao Lu, Stephen J. Picken and Zeynep Yildirim
Chemical Communications 2007 (Issue 12) pp:1245-1247
Publication Date(Web):08 Dec 2006
DOI:10.1039/B614922G
Six new oligomeric nematic liquid crystals are reported consisting of a triphenylene-based core attached to which are six 4-cyanobiphenyl units via flexible alkyl spacers.
Co-reporter:Corrie T. Imrie, Peter A. Henderson and John M. Seddon
Journal of Materials Chemistry A 2004 vol. 14(Issue 16) pp:2486-2488
Publication Date(Web):12 Jul 2004
DOI:10.1039/B404319G
Non-symmetric liquid crystal trimers containing three different mesogenic units and two flexible spacers have been synthesised, and exhibit a new smectic modification, the triply-intercalated alternating smectic C phase.
Co-reporter:Z. Stoeva, C. T. Imrie and M. D. Ingram
Physical Chemistry Chemical Physics 2003 vol. 5(Issue 2) pp:395-399
Publication Date(Web):29 Nov 2002
DOI:10.1039/B208552F
Ionic conductivities of polyethylene oxide (PEO) complexes with LiClO4 have been measured at pressures up to 200 MPa over the temperature range 303–353 K. Two systems differing in phase morphology are compared by reference to their temperature-dependent activation energies and volumes. For an amorphous complex of composition PEO ∶ LiClO4(6 ∶ 1), Vogel–Tammann–Fulcher (VTF) behaviour is found, enabling activation energies to be calculated as a function of temperature from the best fit equation, while activation volumes are obtained directly from the isothermal pressure dependence of the conductivity. While the behaviour of the amorphous complex is adequately described by the free volume model, the corresponding data for a polycrystalline material of overall 20 ∶ 1 stoichiometry suggests the prevalence of surface conduction at lower temperatures. Such variable-pressure, variable-temperature (VPVT) data may in future provide new insights into the behaviour of more complex polymer electrolyte systems.
Co-reporter:Peter A. Henderson, Rachel T. Inkster, John M. Seddon and Corrie T. Imrie
Journal of Materials Chemistry A 2001 vol. 11(Issue 11) pp:2722-2731
Publication Date(Web):08 Oct 2001
DOI:10.1039/B104490G
Three new homologous series of liquid crystal tetramers in which four mesogenic groups are linked via three alkyl spacers have been synthesised and characterised. In each series the length of the outer two spacers, n, is varied from 3 to 12 methylene units while the central spacer is held at 5 methylene units. The three series differ only in the substitution pattern around the inner two mesogenic units. The series in which the inner spacer is attached to the 4-position on both mesogenic groups is referred to as n-p5p-n while n-p5m-n refers to attachment at the 4-position on one group and the 3-position on the other. n-m5m-n refers to attachment at the 3-position on both groups. All the members of the n-p5p-n and n-p5m-n series exhibit nematic behaviour. The nematic–isotropic
transition temperatures exhibit a pronounced alternation as the length and parity of the outer spacers are varied but which attenuates as n is increased. By contrast, the odd–even effects shown by the associated entropy changes are not attenuated as n is increased. 4-p5m-4 and 5-p5m-5 also exhibit smectic behaviour. 4-m5m-4 shows a nematic phase and an alternating smectic phase analogous in structure to that observed for certain semi-flexible main chain liquid crystal polymers. The n-m5m-n compounds with n = 6, 8, 9 and 10 also exhibit a nematic phase and a disordered crystalline phase. The trends in the transitional properties of the series are interpreted in terms of average molecular shapes and a model developed to understand the behaviour of liquid crystal dimers.
Co-reporter:Z Jiang, J.M Hutchinson, C.T Imrie
Fuel 2001 Volume 80(Issue 3) pp:367-371
Publication Date(Web):February 2001
DOI:10.1016/S0016-2361(00)00092-2
Temperature modulated differential scanning calorimetry (TMDSC) is used for the first time to measure the wax appearance temperature (WAT) of crude oil samples. The commercial implementation of TMDSC chosen for this study is alternating differential scanning calorimetry (ADSC) marketed by Mettler-Toledo. We show that changes in the ADSC signals exhibit excellent correlations with WATs measured using conventional differential scanning calorimetry, DSC. For oil samples having low wax contents, ADSC is a more sensitive technique for identifying the onset of wax crystallisation and, specifically, the phase angle between the heating rate and heat flow modulations is extremely sensitive to this process.
Co-reporter:Corrie T. Imrie, Zhibao Lu, Stephen J. Picken and Zeynep Yildirim
Chemical Communications 2007(Issue 12) pp:NaN1247-1247
Publication Date(Web):2006/12/08
DOI:10.1039/B614922G
Six new oligomeric nematic liquid crystals are reported consisting of a triphenylene-based core attached to which are six 4-cyanobiphenyl units via flexible alkyl spacers.
Co-reporter:Corrie T. Imrie and Peter A. Henderson
Chemical Society Reviews 2007 - vol. 36(Issue 12) pp:NaN2124-2124
Publication Date(Web):2007/10/17
DOI:10.1039/B714102E
The underlying theme of this Critical Review is the relationship between molecular structure and liquid crystalline behaviour in a class of materials referred to as liquid crystal oligomers. For the purposes of this review, a liquid crystal oligomer will be defined as consisting of molecules composed of semi-rigid mesogenic units connected via flexible spacers. Much of the review will be devoted to structure–property relationships in the simplest oligomers, namely dimers, in which just two mesogenic units are connected by a single spacer. Along the way we will see how this molecular architecture has been exploited to address issues in a range of quite different areas and has given rise to potential applications for these materials. On the whole, only compounds in which the mesogenic units are linked essentially in a linear fashion will be considered while structures such as liquid crystal dendrimers and tetrapodes fall outside the scope of this review. The review will be of interest not only to scientists working directly in this area but in particular to those interested in understanding the relationships between structure and properties in polymers, and those designing materials for new applications (231 references).
Co-reporter:Toby Donaldson, Peter A. Henderson, Marie France Achard and Corrie T. Imrie
Journal of Materials Chemistry A 2011 - vol. 21(Issue 29) pp:NaN10941-10941
Publication Date(Web):2011/06/06
DOI:10.1039/C1JM10992H
The synthesis and characterisation of two new series of liquid crystal tetramers in which four mesogenic groups are linked via three alkyl spacers is reported. In each series the length of the outer two spacers, n, is varied between 3, 4, 5, 7, 10 and 11 methylene units while the central spacer length, m, is either 5 or 6 methylene units. The outer two mesogenic groups are cholesteryl-based, Chol, while the inner two are Schiff's bases, SB. The tetramers are referred to by the acronym Chol-n-SB-m-SB-n-Chol. All twelve tetramers exhibit an enantiotropic chiral nematic phase. The chiral nematic-isotropic transition temperatures and associated entropy changes depend critically on the combination of spacers in the tetramer and this is interpreted in terms of average molecular shapes. The tetramers with m = 5 and n = 5, 7, and m = 6 and n = 3, 4, 5, 7, show a monolayer chiral smectic C* phase, the driving force for which may be the mismatch in the cross-sectional areas of the differing mesogenic groups. The tetramers with m=6 and n = 10, 11 show a quadruply intercalated smectic A phase characterised by a smectic periodicity to estimated molecular length ratio of just 0.23. The driving force for the formation of this phase is thought to be specific electrostatic interactions between the unlike mesogenic units while the formation of the phase is strongly dependent on the length and parity of the spacers due to packing constraints. On cooling, a new phase transition is seen, possibly driven by conformational changes in the outer flexible spacers, for both these tetramers from the intercalated smectic A phase to an intercalated alternating chiral smectic C* phase in which the layers consist of either the mixed mesogenic groups or solely the cholesteryl-based moieties.
![[1,1'-Biphenyl]-4-carbonitrile, 4',4'''-[[1,1'-biphenyl]-4,4'-diylbis(oxy-5,1-pentanediyloxy)]bis-](http://img.cochemist.com/ccimg/105700/105658-76-2.png)
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-, (E)-](http://img.cochemist.com/ccimg/134900/134871-30-0.png)
-, (E)-](http://img.cochemist.com/ccimg/134900/134871-30-0_b.png)
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-, (1E)-](http://img.cochemist.com/ccimg/157900/157875-88-2.png)
-, (1E)-](http://img.cochemist.com/ccimg/157900/157875-88-2_b.png)
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-, (1E)-](http://img.cochemist.com/ccimg/186300/186249-37-6.png)
-, (1E)-](http://img.cochemist.com/ccimg/186300/186249-37-6_b.png)
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-](http://img.cochemist.com/ccimg/132600/132545-64-3.png)
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