This article was downloaded by: [Duke University Libraries]

On: 02 August 2012, At: 08:12

Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House,
37-41 Mortimer Street, London W1T 3JH, UK

Liquid Crystals
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/tlct20

Synthesis and characterisation of a novel chiral

smectic liquid crystal compound
a a b
S. Essid , Z. Rihab & H.T. Nguyen
a
Laboratoire de Physique de la Matière Molle et de la Modélisation électromagnétique,
Faculté des Sciences de Tunis, Tunis, Tunisie
b
Centre de Recherche Paul Pascal, Pessac, France

Version of record first published: 10 May 2012

To cite this article: S. Essid, Z. Rihab & H.T. Nguyen (2012): Synthesis and characterisation of a novel chiral smectic liquid
crystal compound, Liquid Crystals, 39:7, 865-872

To link to this article: http://dx.doi.org/10.1080/02678292.2012.686634

PLEASE SCROLL DOWN FOR ARTICLE

Full terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions

This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to
anyone is expressly forbidden.

The publisher does not give any warranty express or implied or make any representation that the contents
will be complete or accurate or up to date. The accuracy of any instructions, formulae, and drug doses should
be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims,
proceedings, demand, or costs or damages whatsoever or howsoever caused arising directly or indirectly in
connection with or arising out of the use of this material.
 Liquid Crystals,
Vol. 39, No. 7, July 2012, 865–872

Synthesis and characterisation of a novel chiral smectic liquid crystal compound

S. Essida*, Z. Rihaba and H.T. Nguyenb
a
Laboratoire de Physique de la Matière Molle et de la Modélisation électromagnétique, Faculté des Sciences de Tunis, Tunis,
Tunisie; b Centre de Recherche Paul Pascal, Pessac, France
(Received 26 December 2011; final version received 16 April 2012)

A new chiral smectic liquid crystal, (R)-1-methylheptyl-4-[4-(4-heptyloxythiobenzoyloxy)benzoyloxy]-2-fluoroben-

zoate, denoted as C7F2(COS), which has a thiobenzoate group between the two phenyl rings near the alkoxy
chain and is monofluoro-substituted in position 2 of the first phenyl ring near the chiral chain, has been syn-
thesised. Its mesomorphic and ferroelectric properties have been investigated by optical microscopy, differential
scanning calorimetry, the electro-optical method and dielectric measurements. The spontaneous polarisation, tilt
angle, response time, orientational viscosity, relaxation frequency and dielectric strength have been determined as a
function of temperature. The electric-field temperature phase diagram was established and all the results have been
Downloaded by [Duke University Libraries] at 08:12 02 August 2012

compared with those of the C7F2 compound studied previously.

Keywords: chiral smectic liquid crystal; ferroelectric; phase transitions; phase diagram

F
1. Introduction
Since the discovery of “antiferroelectricity” in chiral C7H15O COS CO2 CO2 CH* C6H13 2

smectic liquid crystal [1], research into new com- CH3

pounds possessing the anticlinic phase (SmC∗ A ) and

other subphases such as the incommensurate SmC∗ α
phase and the commensurate ferrielectric phases
(SmC∗ FI1 , SmC∗ FI2 ) has been paid a great deal of 2. Synthesis
attention. This discovery encourages chemists to syn- The compound was prepared by the following route
thesise new materials in order to obtain a good ferro- (see Scheme 1). The chemical structure of the prod-
electric liquid crystal (FLC) having a short response uct was checked by nuclear magnetic resonance
time and a large spontaneous polarisation [1–19]. (NMR) spectroscopy on a Bruker HW 200 MHz
Therefore, Nguyen continues to search for new com- Spectrometer and by Fourier transform infrared spec-
pounds with an aim of understanding the influence of troscopy (Perkin-Elmer 783 Spectrophotometer). The
the molecular structure on the electro-optical prop- final product was found to have a chemical purity
erties and the chemical parameters responsible for exceeding 99.5%.
the appearance and the stabilisation of the SmC∗ A ,
SmC∗ FI1,2 , SmC∗ and SmC∗ α phases. 2.1 (R)-1-Methylheptyl-4-hydroxy-2-
We have already reported the phase sequence, the fluorobenzoate (A)
physical parameters and the phase diagram of the
This was prepared following the method described
C7F2 compound with the following formula [20]:
elsewhere [7, 10, 20].
F
2.2 4’ -Heptyloxythiobenzoyloxy-4-benzoic acid (B)
C7H15O CO2 CO2 CO2 CH* C6H13 1
This was prepared following the method described
CH3
elsewhere [21].

In this paper, we report the main results concerning

2.3 (R)-1-Methylheptyl-4-[4-(4-heptyloxythioben-
the influence of the thiobenzoate group (COS) between
zoyloxy)benzoyloxy]-2-fluorobenzoate (C7F2(COS))
the two phenyl rings near the alkoxy chain on the
phase sequence, the liquid crystalline properties and To a solution of C7F2(COS) (0.24 g, 0.89 mmol)
the E-T phase diagram of the new compound having in CH2 Cl2 (5 ml) was added DCC (N,N  -
the general formula: dicyclohexylcarbodiimide; 0.12 g, 0.5 mmol), DMAP

*Corresponding author. Email: [email protected]

ISSN 0267-8292 print/ISSN 1366-5855 online

© 2012 Taylor & Francis
http://dx.doi.org/10.1080/02678292.2012.686634
http://www.tandfonline.com
 866 S. Essid et al.

CH2O COOH
+ HO CH* C6H13

CH3

a : DCC, DMAP, CH2Cl2

F

CH2O CO2 CH* C6H13

CH3

b : H2, Pd/C, EtAcO

CO2 CH* C6H13 (A)

Downloaded by [Duke University Libraries] at 08:12 02 August 2012

HO

CH3

C7H15O COCl + HS COOH

c : Et3N, CH2Cl2

C7H15O COS COOH (B)

Finally:

(A) + (B)

d : DCC, DMAP, CH2Cl2

C7H15O COS CO2 CO2 CH* C6H13

CH3

Scheme 1. The synthetic route of the C7F2(COS) compound.

(4-Dimethylaminopyridine; 5 mg) and 4-heptyloxy- was recrystallised from absolute ethanol; yield 0.33 g
thiobenzoyloxy-4-benzoic acid (0.33 g, 0.89 mmol). (56%). 1 H NMR (CDCl3 ): δ (ppm): 0.9 (t, 6H, CH3
The mixture was stirred at room temperature of C6 H13 , CH3 of C7 H15 ), 1.2–1.5 (m, 19H, 4CH2
overnight. The solution was filtered, the solvent evap- of C7 H15 , 4CH2 of C6 H13 and CH3 –CHO), 1.6–1.8
orated and the residue purified by chromatography (m, 4 H, 2CH2β ), 4.1 (t, 2H, CH2 –O), 5.15 (m, 1 H,
on silica gel using CH2 Cl2 as eluent. The product O–CH–CH2 ), 7.1 (t, 1H arom. meta to F), 7.23 (m,
 Liquid Crystals 867

4H arom.), 7.9 (m, 2H, ortho and para to F), 8.26 (m, a programmable direct current supply (HP E3632A), a
4 H arom). programmable Keithley multimeter (Model 2000) and
an oven made in our laboratory. The temperature was
controlled to within 0.01◦ C. The cell was filled with
3. Mesomorphic properties the liquid crystal by capillary action in the isotropic
3.1 Analysis phase and slowly cooled into the SmA phase to avoid
the appearance of a focal conic texture [22].
The phase behaviour and transition temperatures were
determined optically using a polarising optical micro-
scope (POM) fitted with a Mettler FP5 microheating
stage. Transition enthalpies were obtained by differen- 3.2 Phase behaviour
tial scanning calorimetry (DSC) measurements using On cooling from the isotropic liquid, brown stripes
a Perkin-Elmer DSC7. Heating and cooling rates were appear which grow and curl up to form focal conic
5◦ C/min. In the dielectric spectroscopy setup, the volt- defects. This classical texture is characteristic of the
age generator is a Tektronix AWG 2021 delivering a SmA phase. On further cooling no obvious change
static voltage up to 5 V connected to an amplifier in the colour of the texture was observed. Indeed,
(Krohn-Hite Model 7500 Amplifier). Measurements the SmC∗ α phase is hardly detectable by microscopy
Downloaded by [Duke University Libraries] at 08:12 02 August 2012

of the in-phase and the in-quadrature responses are because its texture is similar to that of the SmA phase.
given by a 7280 DSC Lock-in amplifier. The com- On further decreasing the temperature, the SmC∗ A
plex dielectric constant  ∗ ( ∗ =   − j  ) (was mea- phase appears, which is known by the appearance of
sured either at a constant frequency during continuous a striated fan-shaped crystal growing perpendicular to
cooling of the sample or at stabilised temperatures, the rubbing direction. In addition, a change of the
and applying a constant bias field while varying the colour sample can be clearly seen.
frequency from 100 Hz to 1 MHz. The measuringa.c. DSC measurements reveal the existence of two
electric field was about 0.6 Vpp (V peak to peak). overlapping bumps and not well defined peaks indi-
During the experiments, the sample texture cating the presence of three phases, where transition
was automatically monitored with a digital camera temperatures between the different phases are difficult
mounted on a microscope (Leitz Model Laborlux to determine exactly.
12 Pols) and connected to a computer, making the As can be seen in Figure 1, the temperature depen-
identification of phases and phase transitions more dence of the imaginary part of the complex permittiv-
reliable. ity allows us to locate the phase transition sequence
The dielectric spectra were fitted with the following at zero fields. On cooling from the paraelectric SmA
formulae, phase the plot of   shows two maxima which cor-
responds to two transition temperatures, denoted as
 0 − ∞ SmA–SmC∗ α and SmC∗ α –SmC∗ A and produced at
  (ω) = ∞ + (1)
1 + ω2 τ 2 98.2 and 93.8◦ C respectively. We note that the peak at

(0 − ∞ )ωτ
  (ω) = , (2)
1 + ω2 τ 2

where   and   are the real and imaginary parts of

the complex permittivity respectively, ω is the angu-
lar frequency of the applied a.c. electric field, τ is the
relaxation time and 0 and ∞ are the static and the
high frequency dielectric permittivity respectively.
Electric-field-dependent properties and a dielectric
investigation of the studied compound have been stud-
ied using planar alignment commercial cells (EHC,
Japan) coated with indium tin oxide (ITO) layers and
treated with parallel rubbed polyimide. Planar geome-
try was achieved and the cell spacing was about 5.6 μm
and the active area was 25 mm2 . It made a capacitor at Figure 1. Temperature dependence of the imaginary part of
most 1 nF in series with a 2 K resistor thus giving a the dielectric permittivity of the studied compound in cool-
cut-off frequency of a few hundred kHz for dielectric ing runs at a frequency of 7 kHz. The dashed lines indicate
experiments. The temperature regulator is ensured by exactly the ground phase transitions at T C1 and T C2 .
 868 S. Essid et al.

Table 1. Domain existence (◦ C) of the SmA, SmC∗ α and

SmC∗ A for the C7F2 and the C7F2(COS) compounds.

T (SmA) T (SmC∗ a ) T (SmC∗ A )

C7F2 37.2 3.8 43.6

C7F2(COS) 66.3 4.4 26.8

found to be the opposite. Indeed, when the longitu-

dinal moment reached a certain value, the SmC∗ A
phase disappeared. Table 1 summarises the domain of
existence of the different phases when replacing the
benzoate core by a thiobenzoate derivative.

4. Electro-optic studies
Downloaded by [Duke University Libraries] at 08:12 02 August 2012

Figure 2. The imaginary part of the dielectric permittivity of

the studied compound as a function of frequency and tem- 4.1 Experimental procedure
perature, measured on cooling from the isotropic liquid to
Electro-optical properties were observed with the
the crystal phase.
polarising microscope and an oscilloscope (Agilent:
DSO5052A). All measurements were performed using
TC1 is due to the electroclinic effect while the peak at a classical electro-optical set-up for the measurement
TC2 is due to a second mode. of switching current, tilt angle, orientationnal viscosity
Combining the three methods gives us the phase and the electric response time [23].
sequence and the transition temperatures on cooling
runs of the studied compound:
Cr (67◦ C)–SmC∗ A (93.8◦ C)–SmC∗ α (98.2◦ C)–SmA 4.2 Temperature dependence of electro-optic
(164.5◦ C)–Iso. parameters
The variation of the imaginary component of the 4.2.1 Spontaneous polarisation
complex dielectric permittivity as a function of tem- The measurements were performed under a rectangu-
perature and frequency is shown in Figure 2. At the lar a.c. field (ν = 50 Hz) at saturation. The current
SmA–SmC∗ α phase transition, the dielectric losses response is the sum of the charge of the cell capaci-
present a maximum then it decreases with tempera- tor, the ionic conductivity and a hump linked to the
ture. The observed relaxation process corresponds to polarisation which reads:
the soft mode linked to field-induced fluctuations in θ , 
also called the electroclinic effect. ∂Pz
ip (t) = ( )dx dy (3)
At the SmC∗ α –SmC∗ A phase transition, the relax- ∂t
ation process presents the same properties (same order
of magnitude). The observed absorption of this mode and corresponds to the derivative versus time of the
can be attributed to distortion of the helical structure. projection of the macroscopic polarisation P over the
Both compounds (1 and 2), possess the same direction z of the applied field. In all the phases, the
ground sequence including SmC∗ A –SmC∗ α –SmA applied field was strong enough to induce the saturated
phases. The trend in stability of these phases with ferroelectric state. The signal is digitised by the oscil-
short flexible chains also appeared to be similar to loscope and averaged over 64 periods. The data are
that of series previously studied. A comparison of the stored in a computer for further treatment by a sim-
range of existence of the SmA and SmC∗ α phases of ple program to obtain the various parameters under
the two compounds clearly evidences the role of the investigation. A typical sketch of the current response
longitudinal local dipole moment in the stabilisation in the SmC∗ α and SmC∗ A phases is given in Figure 3.
of the two phases (see Table 1). This behaviour The temperature dependence of the spontaneous
confirms the results reported in the previous paper polarisation values is shown in Figure 4. The polari-
[6], which shows that the temperature range of the sation diminishes with increasing temperature, with a
SmA and SmC∗ α phases increases with an increasing maximum value of 32 nC/cm2 . This PS value was rel-
longitudinal moment of the rigid core in the vicinity atively low compared to those of the C7F2 compound
of the non-chiral chain. However, the effects of this (∼60 nC/cm2 ) and many three-ringed compounds
increase on the temperature range of the SmC∗ A was [5–7].
 Liquid Crystals 869

Figure 5. Apparent tilt angle versus temperature at satura-

tion field (E = 4.3 V/μm, ν = 0.2 Hz).
Downloaded by [Duke University Libraries] at 08:12 02 August 2012

low frequency (0.2 Hz), using the usual 2θ optical

method [24]. Measurement accuracy is estimated to be
±0.5◦ C. This parameter decreases as the temperature
approaches the SmA–SmC∗ α transition temperature.
As for the polarisation, the apparent tilt angle ver-
sus temperature curve showed the same behaviour. Its
maximum value was about 16◦ , while it reaches 19.5◦
for the C7F2 compound.

Figure 3. Switching current for (a) the SmC∗ α phase at 4.2.3 Response time
96.4◦ C with E = 4.3 V/μm and (b) the SmC∗ A phase at As known, the electric response time is the time
86.6◦ C with E = 4.6 V/μm. ν = 50 Hz, under a rectangular
required for the majority of molecules to switch under
electric field.
an a.c. field. It corresponds to the top of the polar-
isation peak. The temperature dependence is shown
in Figure 6. Obviously the electric response time
decreases gradually with increasing temperature and
changes from 10.6 μs at 87◦ C to 3.4 μs at 92.6◦ C. This
compound shows a relatively fast switching time, com-
pared to that of the C7F2 compound, where it varies
from 12.4 μs at 88.8◦ C to 3.6 μs at 103◦ C. It is well
known that the response time is proportional to the
viscosity; therefore the very short response time must
be due to its low viscosity.

4.2.4 Rotational viscosity

The rotational viscosity at saturation η was deter-
mined by the following equation:
Figure 4. Polarisation versus temperature at saturation elec-
tric field (E = 4.3 V/μm, ν = 50 Hz). η = τ PS E,

4.2.2 Apparent tilt angle where τ is the response time, PS is the sponta-
neous polarisation and E is the applied electric
The temperature dependence of the tilt angle θ is field.
shown in Figure 5. It was measured with the same The temperature dependence of the rotational vis-
field as for the polarisation measurements but at very cosity is shown in Figure 7. It has the same behaviour
 870 S. Essid et al.

Figure 6. Electric response time versus temperature at satu-

Downloaded by [Duke University Libraries] at 08:12 02 August 2012

ration field (E = 4.3 V/μm, ν = 50 Hz).

Figure 8. Field dependence of the polarisation at (a) 96.6◦ C

and (b) 91◦ C. Applied electric field: rectangular wave at
50 Hz.

Figure 7. The rotational viscosity versus temperature at

saturation field (E = 4.3 V/μm, ν = 50 Hz). occurs via an intermediate ferroelectric phase with
macroscopic polarisation being about a third of the
SmC∗ polarisation as shown in Figure 8(a). In addi-
as for the electric response time, where it decreases tion, microscopic observations show that on further
with increasing temperature and changes from around increasing the applied field, three colours have been
0.011 (T = 87◦ C) to 0.003 poise (T = 92.6◦ C); clearly seen, from a brown SmC∗ A , to a light brown
however, it varies from 0.006 (T = 103◦ C) to 0.04 poise (ferri) and finally to the red unwound SmC∗ .
(T = 88.8◦ C) for the compound 1. At higher temperature range (T < 92.6◦ C) one
sees only one direct transition to the unwound SmC∗
(Figure 8(b)). This behaviour is confirmed by micro-
4.3 Transition under an applied electric field scopic observations of texture change, where only two
In the electro-optic investigations, the transitions to colours were observed.
the unwound ferroelectric phase were determined by In the vicinity of the SmA–SmC∗ α phase tran-
measuring the threshold fields when applying a rect- sition, a pseudo transition temperature is clearly
angular wave. It is defined as being the field from observed, due to the electroclinic effect [25]. This
which the peak of polarisation appears or changes its behaviour is clearly seen in the C7F2 compound [26].
amplitude suddenly.
In the lower temperature range (T < 92.6◦ C),
two threshold fields have been detected (Figure 8(a)). 5. Phase diagram
We see a rapid increase of the induced polarisation In Figure 9, the E–T phase diagram of the C7F2(COS)
accompanied by a small plateau, denoting that the compound is shown, where the phase boundaries
process of unwinding of the ferroelectric SmC∗ phase were obtained by combining electro-optic properties
 Liquid Crystals 871

effect on the ground phase sequence of the

mesophases, but is significantly observed at the
cleaning point (T Iso–SmA ), where it shifts to a
higher temperature.
(ii) The (COS) group leads to an increase of the tem-
perature range and the stabilisation of the SmA
and SmC∗ α phases, whereas it has an opposite
effect on the anticlinic SmC∗ A phase.
(iii) It was found that all the electro-optical param-
eters of the compound 2 showed the same
behaviour independent of temperature; however,
we note a decrease in all the electro-optical
parameter values compared with those of the
C7F2 compound. This behaviour clearly evi-
dences the role of the local dipole moment.
(iv) It has been shown that the established diagram is
Figure 9. Final phase diagram where the different experi-
Downloaded by [Duke University Libraries] at 08:12 02 August 2012

mental results were put together. similar (same topology) to those determined by
Orihara et al. [29] in the compound MHPOCBC
(4-(1-Methylheptyloxycarbonyl)phenyl 4’-octyl-
and microscopic observation, and the missing ones carbonyloxybiphenyl-4-carboxylate) and its
were successfully determined from the temperature homologues; the C7F2 compound [26]. It
dependence of the dielectric constant under a d.c. is clear that the present diagram has only
bias field, especially the transition boundary near the three triple points (fewer than the C7F2
SmA–SmC∗ α transition temperature. Our results con- compound).
firm that the transition under field from the ground (v) The studied compound seems to be an excellent
tilted phases (SmC∗ α , SmC∗ A ) to the field-induced compound for the study of the SmC∗ α phase, as
SmC∗ phase occurs via an intermediate macroscop- well as the SmC∗ A phase, under applied electric
ically polar state that we call the ferrielectric phase. field using resonant X-ray diffraction. This could
We showed that the theoretical models proposed by determine the structure of the induced ferrielec-
Hamaneh and Taylor [27], and extended by Dhaouadi tric phase, where the sulfur atom is a potential
et al. [28] confirm our results. candidate for this technique. Indeed, this com-
pound exhibits a relatively broad SmC∗ α phase
(∼4.4◦ C) and a direct SmC∗ α –SmC∗ A transition.
6. Conclusion
A new compound with a thiobenzoate group between References
the two phenyl rings near the alkoxy chain and
[1] Chandani, A.D.L.; Gorecka, E.; Ouchi, Y.; Takezoe,
monofluoro-substituted in position 2 of the first H.; Fukuda, K. Jpn. J. Appl. Phys. 1989, 28, L1265–
phenyl ring near the chiral chain has been synthesised L1268.
and characterised. Investigation of its mesomorphic [2] Yamawaki, M.; Yamada, Y.; Mori, N.; Hayashi, H.;
properties reveals the following phase sequence: Suzuki, Y.; Nagi, Y.S.; Kawamura, T.; Ishibashi, H.
SmC∗ A –SmC∗ α –SmA. The characterisation of the In Proceedings of the 9 International Displays Research
Conference, 1989, vol. 3, p. 26.
studied compound indicates the effect of molecu- [3] Yamada, Y.; Yamamoto, N.; Mori, K.; Nakamura, K.;
lar parameters like steric hindrance and local dipole Hagiwara, K.; Suzuki, Y.; Kawamura, I.; Orihara, H.;
moment on the stabilisation of the SmC∗ α and SmC∗ A Ishibashi, Y. Jpn. J. Appl. Phys. 1990, 29, 1757–1764.
phases. Most of the ferroelectric parameters, such as [4] Johno, M.; Chandani, A.D.L.; Lee, J.; Ouch, Y.;
spontaneous polarisation, tilt angle, electric response Takezoe, H.; Fukuda, A.; Itoh, K.; Kitazume, T. Proc.
Jpn. Display, 1989, 22, 12.
time and rotational viscosity, were determined at satu- [5] Da Cruz, C.; Rouillon, J.C.; Marcerou, J.P.; Isaert, N.;
ration. Nguyen, H.T. Liq. Cryst. 2001, 28, 125–137.
The common points and the main points of dis- [6] Faye, V.; Rouillon, J.C.; Destrade, C.; Nguyen, H.T.
agreement of the C7F2 and the C7F2(COS) com- Liq. Cryst. 1995, 19, 47–56.
pounds are as follows: [7] Da Cruz, C.; Rouillon, J.C.; Marcerou, J.P.; Isaert, N.;
Nguyen, H.T. Liq. Cryst. 2001, 28, 1185–1192.
[8] Booth, C.J.; Dunmur, D.A.; Goodby, J.W.;
(i) Replacement of the benzoate group (COO) by Kang, J.S.; Toyne, K.J. J. Mater. Chem. 1994, 4,
a thiobenzoate linkage (COS) has not had any 747–759.
 872 S. Essid et al.

[9] Dong, C.C.; Hird, M.; Goodby, J.W.; Styring, P.; Toyne, [20] Essid, S.; Manai, M.; Gharbi, A.; Marcerou, J.P.;
K.J. Ferroelectrics 1996, 180, 245–257. Rouillon, J.C.; Nguyen, H.T. Liq. Cryst. 2004, 31,
[10] Da Cruz, C.; Grelet, E.; Rouillon, J.C.; Marcerou, J.P.; 1185–1193.
Sigaud, G.; Pansu, B.; Nguyen, H.T. Liq. Cryst. 2001, [21] Nguyen, H.T.; Rouillon, J.C.; Cluzeau, P.; Sigaud,
28, 1415–1423. G.; Destrade C.; Isaert, N. Liq. Cryst. 1994, 17,
[11] Cluzeau, P.; Nguyen, H.T.; Destrade, C.; Isaert, N.; 571–583.
Barois, P.; Babeau, A. Mol. Cryst. Liq. Cryst. 1995, 260, [22] Rosenblatt, C.S.; Pindak, R.; Clark, N.A.; Meyer, R.B.
69–91. J. Phys. 1977, 38, 1105–1115.
[12] Nguyen, H.T.; Twieg, R.J; Nabor, M.F.; Isaert, N.; [23] Dupont, L.; Glogarova, M.; Marcerou, J.P.;
Destrade, C. Ferroelectrics 1991, 121, 187–204. Nguyen, H.T.; Destrade, C. J. Phys. II 1991, 1,
[13] Destrade, C.; Simeao, P.; Nguyen, H.T. Ferroelectrics 831–844.
1996, 177, 161–172. [24] Martinot-Lagarde, P.; Duke, R.; Durand, G. Mol.
[14] Nohira, H.; Nakamura, S.; Kamei, M. Mol. Cryst. Liq. Cryst. Liq. Cryst. 1981, 75, 249–286.
Cryst. 1990, 180, 379–388. [25] Garoff, S.; Meyer, R.B. Phys. Rev. Lett. 1977, 38,
[15] Nakamura, S.; Nohira, H.M. Mol. Cryst. Liq. Cryst. 848–851.
1990, 185, 199–207. [26] Essid, S.; Bitri, N; Dhaouadi, H.; Gharbi, A; Marcerou,
[16] Kusumoto, T.; Ogino, K.; Sato, K.; Hiyama, T.; J.P. Liq. Cryst. 2009, 36, 359–364.
Takehara, S.; Nakamura, K. Chem. Lett. 1993, 22, [27] Hamaneh, M.B.; Taylor, P.L. Phys. Rev. E 2005, 72,
1243–1246. 021706(1)–021706(9).
Downloaded by [Duke University Libraries] at 08:12 02 August 2012

[17] Michael, H. Liq. Cryst. 2011, 38, 1467–1493. [28] Dhaouadi, H.; Bitri, N.; Essid, S.; Soltani, T.;
[18] Chakraborty, A.; Das, B.; Das, M.K.; Findeisen- Gharbi, A.; Marcerou, J.P. Phys. Rev. E: Stat.,
Tandel, S.; Tamba, M.-G.; Baumeister, U.; Kresse, H.; Nonlinear, Soft Matter Phys. 2009, 80, 031712(1)–
Weissflog, W. Liq. Cryst. 2011, 38, 1085–1097. 031712(7).
[19] Kaspar, M.; Novotna, V.; Hamplova, V.; Podoliak, N.; [29] Orihara, H.; Naruse, Y.; Yagyu, M.; Fajar, A.; Uto, S.
Nonnenmacher, D.; Giesselmann, F.; Glogarova, M. Phys. Rev. E: Stat., Nonlinear, Soft Matter Phys. 2005,
Liq. Cryst. 2011, 38, 309–317. 72, 040701(1)–040701(4).