Phase Transitions

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Optical measurements of phase transitions in

difluorophenylazophenyl benzoate thermotropic
liquid crystal with specific orientated fluorine
atoms

A. A. Zaki

To cite this article: A. A. Zaki (2019) Optical measurements of phase transitions in

difluorophenylazophenyl benzoate thermotropic liquid crystal with specific orientated fluorine atoms,
Phase Transitions, 92:2, 135-148, DOI: 10.1080/01411594.2018.1556271

To link to this article: https://doi.org/10.1080/01411594.2018.1556271

Published online: 11 Dec 2018.

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PHASE TRANSITIONS
2019, VOL. 92, NO. 2, 135–148
https://doi.org/10.1080/01411594.2018.1556271

Optical measurements of phase transitions in

difluorophenylazophenyl benzoate thermotropic liquid
crystal with specific orientated fluorine atoms
A. A. Zakia,b
a
Physics Department, College of Sciences, Taibah University, Yanbu, Saudi Arabia; bFaculty of Sciences, Physics
Department, Banha University, Banha, Egypt

ABSTRACT ARTICLE HISTORY

Phase transition temperature and optical properties of the special oriented Received 27 July 2018
fluorine atoms in difluorophenylazophenyl Benzoate Thermotropic Liquid Accepted 3 December 2018
Crystal nominated (III) were studied and measured. Absorbance and
KEYWORDS
transmittance in the visible region at room temperature for the Phase transition; optical
compound III dissolved in methylene chloride of different parameters; modified
concentrations were determined. The maximum absorbance for the spectrophotometer;
compound III was in the blue region (447 nm) and the molar absorption refractive index;
coefficient was found to be 0.93 (L. mMol−1.cm−1). The transition birefringence; order
temperature was determined for the thermotropic LC compound III by parameter
using DSC, POM and modified spectrophotometer techniques. Nematic
and smectic phases during the cooling process were observed. Ordinary
and extraordinary refractive indices, birefringence, order parameter and
the molecular polarizability were determined with different
temperatures for the LC phases of compound III.

1. Introduction
Liquid crystals (LCs) have properties between solid crystal and isotropic liquid. Many LC com-
pounds exhibit one or more distinct mesophases that depend on the basis of molecular order
such as nematic (N) and layered Smectic (Sm) phases [1–3]. The use of LC in different applications
depends on various parameters such as optical transmittance, absorption coefficient, order par-
ameter, dielectric constant, birefringence, etc. The transmittance in thermotropic LCs, for a large
interval of temperature, has been investigated in the nematic mesophase and isotropic liquid [4].
The refractive index and birefringence measurements were obtained by means of an Abbe refract-
ometer and wedge method and Newton’s ring technique for the N and Sm A phases and the N-
Sm A transition in LCs has been studied [5–8]. Yildiz et al. [9] measured the ordinary and extraordi-
nary refractive indices of 10.O.4 by means of an Abbe refractometer. Also, the optical birefringence
based on a rotating-analyzer method was measured [10,11]. Moreover, the temperature dependence
of the ordinary (no) extraordinary (ne) refractive indices, and birefringence (Δn) for thermotropic
LCs mesogens are studied [12–17]. The influence of lateral substituent of different kinds of meso-
genic such as fluorine atoms on the optical parameters have been studied [18–20].
The orientation effect of two laterally fluorine atoms on the optical properties of difluoro substi-
tuted-4-(2’-(or 3’-) fluorophenylazo)-2-(or3-) fluoro phenyl-4’’-dodecyloxybenzoates thermotropic
liquid crystals (I & II) was investigated. When the two fluorine atoms are directed towards the mol-
ecular core as in compound I, the nematic phase was observed during heating and cooling processes

CONTACT A. A. Zaki ayman_a73@hotmail.com

© 2018 Informa UK Limited, trading as Taylor & Francis Group
136 A. A. ZAKI

while the smectic phase appears when the two atoms are directed outwards the molecular core as in
compound II. Refractive indices, birefringence, order parameters and thermal stability factors for
compounds I and II were measured [21]. This work aims at complete the previous work for the criti-
cal effect of the special lateral location and orientation of two fluorine atoms on the phase transition
and optical properties of the compound difluoro substituted-4-(2’-(or 3’-) fluorophenylazo-2-(or 3-)
fluoro phenyl-4’’-dodecyloxybenzoates thermotropic LC, where one atom of fluorine is directed
towards the core of the molecule while the other atom is directed outwards, this compound was
nominated as compound (III). The optical parameters such as ordinary and extraordinary refractive
indices, birefringence, order parameter and polarizability were measured.
Fluorine substitution makes little change in the molecular shape, but changes do exist in the
polarity and location of dipole moments. The polar lateral group of fluorine atoms has an effect
on the lateral polarizability and the lateral dipole moment of the molecule to an extent dependent
on its position and polarity. This is reflected on the mesomorphic characteristics of the resultant
molecule.

2. Preparation of the compound

The liquid crystal compound III has the chemical structure as shown in Figure 1 and the elemental
analyses were listed in Table 1. The Infrared spectra were measured for the investigated compound
III with a Perkin-Elmer B25 spectrophotometer (Perkin-Elmer, Inc., Shelton, CT USA) as collected
in Table 2. The C = O stretching absorption (υC=O) appears at 1732 cm−1, as a result of the electron-
withdrawing effect of the lateral F-atom irrespective of their locations as seen in Table 2 [21,22].

3. Results and discussion

3.1. UV-Vis spectrophotometer
UV-Vis spectrophotometer (UV-1800 SHIMADZU, Japan) of ranging wavelength (200-800 nm)
was used to measure the transmission and absorption for the compound III dissolved in methylene
chloride of different concentrations (0.1–0.5 mMol/L) at room temperature (300 K). It was found
from Figure 2(a) that the transmission intensity decreases as the concentration increases. Also,
this compound is observed to have high transmittance and low scattering for a wavelength greater
than 500 nm. As shown in Figure 2(b), the absorption maximum was centered about the maximum
wavelength (λmax = 447 nm), which means that the compound III has a relatively strong absorption
in the blue region due to n-π* transition of N = N chromophore. There is a slight blue shift in maxi-
mum absorbance wavelength from (452–444 nm) by increasing the concentration from (0.1–
0.5 mMol/L).
The relation between maximum absorbance (A) at (λmax) and concentrations (C ) of compound
III is shown in Figure 3, this relation is found to be directly proportional. The slope of this plotting
gives the molar absorption or extinction coefficient ε of the compound by Beer’s Lambert law [23],
1 = A(max )/Cd, where d is the thickness of the sample cell. The value of ε for compound III is
obtained as 0.93 (L. mMol−1.cm−1).

Figure 1. Chemical structures of the compound III.

 PHASE TRANSITIONS 137

Table 1. The elemental analyses for the compound III.

Analyses calculated (found)
%C %H %N %F
71.24(71.23) 6.94(6.91) 5.36(5.31) 7.27(7.21)

3.1.1. DSC transition temperature

The phase transition temperature in Kelvin degrees (K) for the LC compound III was investigated by
using differential scanning calorimetry (DSC) with a temperature scanning rate 2 °C/min during the
measurements as shown in Figure 4 and as listed in Table 3. Figure 4 shows the DSC thermogram of
compound III during the cooling process. It was observed that the LC compound III shows N phase
during both heating and cooling processes but it shows Sm A phase during the cooling process only,
which is considered the correction and addition to this compound [22]. The liquid crystal sample
used has monotropic phases which appear only on the cooling process due to its less stability and
the smectic phase occurs below the melting temperature of the sample [1–3]. The symbols Cr–N,
N–I, N–Sm and Sm–Cr, in Table 3 represent the transition from solid crystal to N, N to isotropic,
N to Sm A and Sm A to solid crystal respectively.

3.1.2. POM transition temperature

The polarizing optical microscope (POM) (Wild, Germany), with a homemade hot-stage, Brookfield
temperature controller from England with a thermocouple is used for measuring the phase transition
temperature and the texture appears by the LC mesogens. The morphological textures of compound
III were presented in Figure 5, which represent the N threaded texture, Sm A and crystalline phases
at 350, 330 and 313 K, respectively. These photos are taken when the material was placed between
two crossed polarizers with magnification of 100X. The phase transition temperature detected by
POM was in accordance with those obtained by DSC as in Table 3.

3.1.3. Measuring phase transition by modified spectrophotometer

The optical setup of modified spectrophotometer (MS) technique which can be used as a new
method for determining the phase transition temperature by the transmission spectra during heating
and cooling is shown in Figure 6, where D is the diffraction grating, R is the rotating disc (Sample,
blank, shutter), M is the mirror, B is the beam splitter, P1 and P2 are the polarizer and analyzer and S
is the sample inside the electric oven. The sample of homogeneous alignment was sandwiched
between two cover slides of glass and separated by four spacers with thickness 40 µm in uniform
planar orientation with a director parallel to the cell walls. To prevent the leakage of the material
by melting, the edges and end parts of the LC cell were sealed with a heat resistant adhesive.
After that, the sample cell was placed inside an electric oven with heating control system of rate
1°C/min, and the whole system was then placed between two polarizers. The same two glass
cover slides as a reference cell were put between two polarizers without placing a sample between
them. The transmitted light intensity was measured as a function of temperature and wavelength
for compound III during the heating and cooling processes. Figure 7 shows the variation of trans-
mittance with wavelength at certain temperatures, as a representative example of obtained data, for
compound III. As in this figure the transmission increases directly with wavelength from 400 to
500 nm and then becomes almost constant until 750 nm, except for the small peak that appears
near 640 nm due the backlight illumination, where the color of the sample is yellowish-reddish,
after that transmittance increases in a direct relationship with wavelength at 740 nm.

Table 2. Characteristic infrared absorption bands (in cm−1) for compound III.
Comp. νCH3Asym. νCH3 Sym. νC=O νC=N. νC-O νC-O
III 2921 2852 1732 1600 1487 1258
138 A. A. ZAKI

Figure 2. (a-b) Optical transmittance and absorbance spectra of compound III at different concentrations.

Figure 3. The relation between maximum absorbance and concentrations of compound III.

Also, the transmitted light intensity was measured as a function of temperature at certain
wavelength for compound III during the heating and cooling processes as seen in Figure 8. It
was found in Figure 8 that the transmission intensity increases abruptly due to the transition
from solid to LC phase and then decreases rapidly through isotropic phase during the heating

Table 3. Phase transition temperatures in Kelvin (K) for the compound III by using DSC, POM and MSP techniques.
Technique Heating Cooling
TCr-N (K) TN -I (K) TI -N(K) TN -Sm (K) TSm-Cr (K)
DSC (K) 352.5 374 370 337 322.5
POM (K) 354 372 372 336 322
MS (K) 353 373 368 335 323
Cr – solid crystal; N – nematic; Sm – smectic; and I – isotropic.
 PHASE TRANSITIONS 139

Figure 4. DSC thermogram of the compound III.

process and the opposite occurs during the cooling process. Note that the kind of LC phase was
identified by using (POM) technique. The change of transmittance during LC phase occurs due to
the rotation of the compound mesogens. The phase transition temperatures resulted by this tech-
nique were in accordance with that obtained by DSC and POM methods with very little change as
in Table 3.

3.2. Measuring of refractive indices

Refractive indices at different degrees of temperature were measured by using Abbe refractometer
technique with the heating control unit of thermostat within ±0.1°C around the prisms made by Bel-
lingham, England. He–Ne laser of wavelength (543 nm) was used as a source of light. For measuring
the refractive indices no and ne, the refractometer prisms were modulated to obtain the planar and
homeotropic alignment required in the LC sample. The compound was exposed to a linearly polar-
ized light and the data was taken during the heating and cooling processes with an accuracy of
±0.0005 as shown in Figure 9. It was noticed that the values of no increase as the temperature increase
while that of ne decrease as the temperature increase.
The effective geometry parameter αeg is an important parameter for understanding the light
spreading in LC and is connected with the director field orientation of the liquid crystals [24].
This parameter for LC is determined by [25]:
no
aeg = . (1)
ne
The values of αeg for compound III depend on temperature as shown in Figure 10, where its mag-
nitude increase with increasing temperature in the N and Sm A mesophases. The value of αeg reached
to unity at the isotropic phase transition which means that the orientational order in LC material
vanished [26–28].
140 A. A. ZAKI

Figure 5. Optical photomicrographs of compound III for the nematic, semictic and crystalline phases at 350, 330 and 313 K,
respectively.

3.3. Birefringence measurements

Birefringence Δn of the LC is one of the fundamental interests and is the key parameter which affects
the operation of LC based electro-optic devices [29–31]. The values of (Δn = ne – no) for compound
III are determined from the measured values of no and ne with different temperatures at wavelength
of laser (543 nm) as shown in Figure 11. It was observed that the values of Δn decreases gradually
with increasing temperature and there is a slight change in Δn at the N–Sm A region of the phase
transition [26–32]. The values of Δn for compound III in N phase between (0.10–0.17) are smaller
than that in the Sm phase between (0.2–0.25) as a function of the temperature which may be attrib-
uted to the higher molecular alignment in the Sm A phase [20,26,33].
Birefringence (Δn) can be measured also from the light intensity passing through the sample in
LC phase by using the equation as follow [22,33–35]:








l T⊥ (l)
Dn = sin−1 . (2)
pt T (l)

The values of T⊥ and T‖ at certain wavelength and temperature were measured for compound III.
The thickness t of sample equals 40 µm, which was measured by using traveling microscope. The
 PHASE TRANSITIONS 141

Figure 6. Optical set-up of the modulated spectrophotometer technique, where D: diffraction grating; R: rotating disc (Sample,
blank, shutter); M: mirror; B: beam splitter; P1 and P2 are polarizer and analyzer; S: sample inside the electric oven.

Figure 7. The variation of transmittance with wavelength at certain temperatures for compound III.

Table 4. The values of the birefringence (Δn) at different temperatures, where (T⊥, T||) are normal and parallel transmittance in
nematic and smectic phase at (543 nm) respectively for compound III.
Nematic Smectic
Temp. (K) T⊥ T|| Δn Temp. (K) T⊥ T|| Δn
350 18 31 0.153 325 12 15 0.23
360 22 41.7 0.189 328 11.5 15 0.22
142 A. A. ZAKI

Figure 8. Transmittance temperature dependence at certain wavelength (543 nm) for compound III.

Figure 9. Temperature dependence of refractive indices (no & ne) for compound III in nematic and smectic LC phases at 543 nm.

values of Δn of compound III in N and Sm A phases at wavelength 543 nm of laser light under cer-
tain temperatures were listed in Table 4. These results are nearly the same as the values of Δn
obtained from Abbe refractometer within error (±0.005) at the same temperature degrees and
wavelength.
 PHASE TRANSITIONS 143

Figure 10. The effective geometry parameter αeg varies with temperatures for LC compound III in nematic and smectic LC phase at
543 nm.

Figure 11. Temperature dependence of birefringence for compound III in nematic and smectic phase at 543 nm.

3.4. Order parameter measurement

The refractive indices data have been used to detect the orientational or microscopic order parameter
S of the LC compound III. The order parameter S can be determined by using Vuks hypothesis as
144 A. A. ZAKI

follow [36,37]:
 
Da (n2 − n2o )
S = e2 , (3)
a n −1
where Δα is the polarizability anisotropy and α is the mean molecular polarizability. By using Haller’s
extrapolation method the order parameter S can be obtained by plotting [(n2e – n2o)/(‹n2›-1)] as a func-
tion of ln [1-(T/Tc)], where TC is the clearing temperature of the LC sample (the transition temp-
erature from LC to isotropic phase) [31,38,39]. From the extrapolated interception of a straight
line graph at T = 0 K, the value of scaling factor Δα/α where S = 1 was determined. It was noticed
that the scaling factor remain the same for all temperatures. Substituting the obtained values of
Δα/α (equal 0.4476, 0.6395 for N and Sm A phases respectively) in eq. (3), the values of S can be
evaluated for compound III. Figure 12 shows the values of S as a function of temperature in N
and Sm phases for compound III. It was observed that the values of S, in Sm A phase, is higher
than that in the N phase which reflects the enhancement of the orientational order parameter in
this phase. The order parameter decreases monotonically with temperature and increases monoto-
nically with optical anisotropy as shown in Figures 12–13. Also, the relation between the effective
geometry parameter αeg with S for LC compound III is shown in Figure 14. The parameter αeg
decreases with increasing birefringence and order parameter in Smectic and nematic phases.

3.5. Molecular polarizabilities

Molecular polarizability is an important parameter for liquid crystals. The ordinary (αo) and extra-
ordinary (αe) polarizabilities representing the electric vector perpendicular and parallel to the optic
axis of the LC are given by Vuks’ method as [40,41]:
  2 
3 ne − 1
ae = , (4)
4pN n2 + 2
  2 
3 no − 1
ao = , (5)
4pN n2 + 2

Figure 12. The relation of order parameter S with temperature for the nematic and smectic phases of compound III.
 PHASE TRANSITIONS 145

Figure 13. The order parameter relation with birefringence for compound III.

where N = NA ρ/M is the number of molecules per cm3, NA is the Avogadro number, ρ is the density
of the liquid crystal molecules and M is the molecular weight of the liquid crystal sample [22], and
‹n2› is the mean square value of the refractive index which is given as follows:

n2e + 2n2o
n2 = . (6)
3

Figure 14. The relation between the order parameter S and the effective geometry parameter αeg for compound III.
146 A. A. ZAKI

Figure 15. The relation between the molecular polarizability α and temperature for compound III.

The values of αe and αo for N and Sm A phases of compound III at different temperatures are shown
in Figure 15. As seen in this figure, the values of αe increase as the temperature decrease, while those
of αo increase as the temperature increase and the temperature dependence of αe and αo exhibit the
same behavior as that of birefringence.

4. Conclusion
The absorbance and transmittance for compound III when dissolved in methylene chloride of different
concentrations were investigated at room temperature in UV-Visible spectra. The maximum absorption
band was observed in the blue region (447 nm) and the molar absorption coefficient was found to be 0.93
(L. mMol−1.cm−1) for compound III. The phase transition temperature for the thermotropic LC com-
pound III was investigated during the heating and cooling processes by using DSC, POM and MS tech-
niques. The thermogram of the compound is obtained by using the DSC technique whereas the POM
technique clarifies the morphological textures of the compound. The third new technique (MS) deter-
mines both the phase transition and the birefringence measurements of the sample. So the three methods
are used to complement and compare the data obtained. Compound III has nematic and smectic A
phases during the cooling process. Optical parameters such as refractive indices (no & ne), birefringence,
microscopic order parameter and molecular polarizabilities for special position and orientation of the
two fluorine atoms of LC compound III were measured. The birefringence and order parameters
were found to be decreases monotonically with the temperature of LC compound III.

Acknowledgements
I wish to express my sincere thanks to assistant Prof. Dr H. A. AHMED Chemistry Department, Faculty of Science,
Cairo University and assistant Prof. Dr Mohamed Hagar, Alex University for their facilities.

Disclosure statement
No potential conflict of interest was reported by the author.
 PHASE TRANSITIONS 147

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