Novel non-symmetric liquid crystal dimer containing bisazobenzene moieties: Synthesis and characterization

Article abstract of DOI:10.1080/15421400903054493

A new series of calamitic liquid crystalline non-symmetric dimer containing bisazobenzene moiety and a rather short alkoxybiphenyl linked by flexible spacers (4-propyloxy-[4-biphenyloxyalkyl]-4′-(4-phenylazo)azobenzene has been designed, synthesized and characterized by spectroscopic methods. The transition temperatures and phase behaviors were studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XRD) analyses. All the synthesized compounds exhibited enantiotropic phase with dimers containing propyl, butyl and octyl flexible alkyl spacers showing SmA and those with pentyl and hexyl spacers exhibited SmA and SmC phases respectively and the stability of the smectic layer depends on the spacer length for the compounds studied. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/15421400903054493

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Molecular Crystals and Liquid
Crystals
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Novel Non-Symmetric Liquid
Crystal Dimer Containing
Bisazobenzene Moieties:
Synthesis and Characterization
A. A. Salisu a , M. Z. Ab. Rahman a , S. Silong a , M.
Bin Ahmad a & M. R. Lutfor b
a Department of Chemistry , University Putra
Malaysia , Selangor, Darul Ehsan, Malaysia
b School of Science, University Malaysia Sabah , Kota
Kinabalu Sabah, Malaysia
Published online: 05 Oct 2009.
To cite this article: A. A. Salisu , M. Z. Ab. Rahman , S. Silong , M. Bin Ahmad & M.
R. Lutfor (2009) Novel Non-Symmetric Liquid Crystal Dimer Containing Bisazobenzene
Moieties: Synthesis and Characterization, Molecular Crystals and Liquid Crystals,
509:1, 134/[876]-144/[886], DOI: 10.1080/15421400903054493
To link to this article: http://dx.doi.org/10.1080/15421400903054493
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Mol. Cryst. Liq. Cryst.
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Novel Non-Symmetric Liquid Crystal Dimer
Containing Bisazobenzene Moieties:
Synthesis and Characterization
A. A. Salisu1, M. Z. Ab. Rahman1, S. Silong1,
M. Bin Ahmad1, and M. R. Lutfor2
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A new series of calamitic liquid crystalline non-symmetric dimer containing
bisazobenzene moiety and a rather short alkoxybiphenyl linked by flexible spacers
(4-propyloxy-[4-biphenyloxyalkyl]-40-(4-phenylazo)azobenzene has been designed,
synthesized and characterized by spectroscopic methods. The transition tem-
peratures and phase behaviors were studied by differential scanning calorimetry
(DSC), polarizing optical microscopy (POM) and X-ray diffraction (XRD) analyses.
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ing propyl, butyl and octyl flexible alkyl spacers showing SmA and those with
pentyl and hexyl spacers exhibited SmA and SmC phases respectively and the sta-
bility of the smectic layer depends on the spacer length for the compounds studied.
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Novel Non-Symmetric Liquid Crystal
1
3
7
/
[
8
7
9
]
SCHEME 1
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1
3
8
/
[
8
8
0
]
A. A. Salisu et al.
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,
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,
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r
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)
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7
.
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(
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,
d
,
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r
H
)
,
C
7
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.
0
0
(
1
4
.
H
,
d
,
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H
s
)
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1
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1
2
.
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(
,
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H
C
,
H
)
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4
.
0
;
6
(
1
H
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s
,
O
C
H
) ,
2
2
.
0
6
2
1
3
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1
H
,
d
,
)
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6
2
(
2
)
,
2
5
s
,
C H )
3
C
N
M
R
(
4
0
0
M
H
z
2
2
C
D
C
7
C
l
)
d
:
1
4
,
7
.
3
1
,
2
2
1
,
2
1
0
.
.
0
3
0
,
0
2
,
1
2
2
5
3
3
.
.
7
4
2
2
8
,
,
2
1
1
9
2
6
.
3
7
.
2
0
7
,
5
6
,
8
1
8
.
3
2
6
5
,
.
7
1
,
.
2
1
9
2
(
9
7
C
2
)
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1
1
6
4
C
.
7
)
8
1
,
1
1
4
.
5
9
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3
(
6
)
,
1
2
2
.
9
9
3
.
0
7
.
1
(
1
3
1
.
2
1
4
.0
8
,
1
5
2
.
8
5
3
,
1
5
.
9
,
.
0
0
(
)
.
2.2.3. 4-propyloxy-[4-biphenyloxypentyl]-40-
(4-phenylazo)azobenzene: BA.O5O.3
Y
i
;
e
N
l
d
,
5
9
:
,
9
%
,
m
C
M
.
p
a
.
l
9
9
–
t
1
e
:
4
0
d
3
7
2 ꢁ
f
7
4
C
.
E
l
e
m
e
n
t
N
a
l
a
O ) ,
3
B
n
a
l
y
s
i
s
7
:
F
o
5
2
u
n
H
3
d
C
,
2
8
2
7
3
6
6
N
2
0
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2
3
9
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1
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;
.
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1
4
H
,
,
,
6
M
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4
0
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3
6
8
;
,
c
u
l
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r
(
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H
C
6
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6
.
14
3
8
3
8
4
1
S m=z
1
5
1
9
5
S m=z
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,
4
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a
M þ
)
m
N
I
a
M
H
R
,
c
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r
1
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H
4 8
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s
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4
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r
l
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d
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0
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d
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q
,
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2
d
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r
(
)
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7
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H
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r
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(
,
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1
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,
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7
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0
2
H
H
,
d
A
r
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)
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.
0
0
4
,
4
.
0
,
t
C
,
1
3
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C
H
)
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.
7
6
(
6
H
,
,
C
)
,
.
5
5
(
2
H
s
C
H
)
2
,
0
(
3
s
,
C
H
;
2
2
3
N
M
R
(
4
0
0
M
H
z
C
D
C
l
)
d
:
2
9
.
7
0
,
1
4
.
1
2
,
2
2
.
1
3
,
2
9
.
5
4
,
6
8
.
0
6
,
7
2
.
2
9
3
(
8
C
)
,
1
1
4
.
7
8
,
1
1
4
.
9
(
6
C
)
,
1
2
2
.
9
9
,
1
2
3
.
0
0
,
1
2
3
.
4
2
,
1
2
3
.
7
5
,
1
2
5
.
0
7
,
1
2
9
.
1
2
(
1
6
C
)
1
3
1
.
2
5
,
1
4
7
.
0
8
,
1
5
2
.
7
8
,
1
5
3
.
3
0
,
1
5
3
.
9
8
,
1
6
2
.
0
0
(
8
)
.

Novel Non-Symmetric Liquid Crystal
1
3
9
/
[
8
8
1
]
2.2.4. 4-propyloxy-[(4-biphenyloxyhexyl)-40-
4-phenylazo]azobenzene: BA.O6O.3
Y
i
e
l
d
6
3
%
,
m
.
p
.
9
5
–
9
C
.
E
l
e
m
e
n
t
a
l
a
n
a
l
y
s
i
s
:
F
o
u
n
d
C
7
6
.
4
4
H
6
M
.
5
8
N
9
:
.
1
6
4
, d
H
d
1
4
1
,
C
a
l
c
u
)
a
N
l
a
I
t
R
c
e
,
, t
R
,
0
H
1
d
(
f
K
)
o
B
,
0
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H
,
r
(
C
c
9
H
N
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)
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,
C
7
6
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1
7
-
1
(
;
H
,
5
.
9
1
-
2
6
H
A
;
0
N
,
8
.
7
8
5
3
4
6
7
;
,
3
9
4
0
4
2
1
S m=z
9
2
(
M þ
r
,
m ꢂ
)
:
2
9
3
8
2
8
6
2
(
C
H
,
t
)
,
2
,
1
,
5
1
4
8
m
,
,
1
4
7
c
r
,
5
z
4
(
.
a
r
o
H
m
t
i
1
3
4
(
C
-
H
,
d
)
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1
2
5
8
0
,
1
4
7
C
4
8
(
C
,
d
)
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8
1
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(
a
2
r
o
a
,
t
i
)
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M
2
.
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4
0
M
H
,
z
7
,
.
C
D
C
l
) d
3
:
.
0
5
)
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(
,
1
r
,
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)
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9
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3
t
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5
5
)
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)
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7
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(
,
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r
H
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s
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4
,
d
,
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r
H
)
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3
H
,
,
O
H
N
)
,
.
7
6
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6
H
2
1
3
1
3
C
)
1
.
(
4
H
,
)
2
0
.
8
5
(
3
H
,
s
,
C H ) ;
3
C
2
2
M
,
R
C
N
7
R
9
2
(
(
4
9
0
C
0
)
M
H
1
C
7
D
,
C
l
1
)
d
:
4
6
.
1
2
,
,
2
1
1
.
0
2
,
,
2
5
.
7
2
,
2
8
.
5
4
3
,
9
.
7
0
6
.
8
7
.
5
0
,
6
,
2
.
2
3
,
1
.
8
1
4
.
9
(
C
)
2
2
.
9
9
1
2
3
.
0
0
,
1
2
.
4
,
1
2
3
1
2
5
.
0
7
,
1
2
9
.
1
2
(
1
6
C
)
1
3
1
.
2
5
,
1
4
7
.
0
8
,
1
5
2
.
7
8
,
1
5
3
.
3
0
,
1
5
3
.
9
8
,
1
6
2
.
0
0
(
8
)
.
2.2.5. 4-propyloxy-[4-biphenyloxyoctyl]-40-
(4-phenylazo)azobenzene: BA.O8O.3
Y
i
N
e
l
d
8
4
4
8
%
,
m
.
p
u
R
.
l
1
2
e
2
d
–
1
2
r
,
,
0
A
H
5 ꢁ
(
c
1
0
r
,
8
C
C
.
E
l
e
m
N
e
n
O ) ,
3
8
, d
C
2
.
H
t
a
l
a
C
8
1
n
7
6
2
:
,
H
8
a
6
2
5
8
A
,
5
l
y
s
i
7
s
:
H
F
o
6
u
n
2
d
N
1
-
C
8
7
6
3
.
8
,
5
5
M
8
8
.
H
,
M
H
S
6
.
9
2
.
7
4
(
4
,
C
a
l
c
a
t
f
o
H
)
.
5
.
7
.
3
4
m ꢂ
1
4
4
4
1
m=z
:
6
0
7
M þ
)
I
m
,
(
K
B
r
)
:
(
2
9
3
,
2
,
) d
,
(
0
C
,
5
-
H
,
t
)
,
6
0
2
,
1
,
4
,
6
7
1
4
9
8
,
1
4
(
a
.
r
H
o
a
N
t
i
c
, t
R
,
0
)
.
3
9
4
C
,
-
H
)
1
1
(
4
8
(
C
d
(
,
H
,
3
H
,
d
)
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9
1
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(
a
2
r
o
m
a
,
t
A
H
.
H
1
i
c
,
d
)
M
(
4
M
H
d
(
.
2
H
,
z
7
C
9
)
,
D
(
4
C
l
.
0
4
H
,
5
,
A
r
H
)
,
7
r
H
3
H
,
t
r
,
H
)
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7
.
5
5
(
2
H
0
d
(
,
1
,
4
1
2
)
,
4
0
.
4
H
0
d
r
H
t
)
,
O
7
.
2
1
H
,
s
,
A
6
)
q
,
,
7
.
0
3
(
,
2
d
,
A
r
H
)
,
7
.
A
H
r
,
H
d
2
,
4
(
6
,
C
H
)
2
1
.
8
2
(
C
1
3
C
H
)
M
,
1
5
5
(
4
H
,
s
) d
1
C
H
.
3
)
.
0
.
(
3
H
,
s
,
C
C
1
)
;
N
7
R
9
2
2
2
3
(
(
4
3
0
0
z
4
C
D
C
l
:
1
4
,
,
2
1
2
,
5
.
7
,
2
8
5
4
,
2
1
9
3
.
0
5
2
(
8
)
2
6
8
.
0
6
1
,
0
5
.
2
3
C
)
1
.
7
8
,
1
4
.
9
(
6
C
)
1
2
.
9
9
1
2
3
.
0
0
,
2
.
4
,
.
7
5
,
2
.
0
7
,
1
2
9
.
1
2
(
1
6
C
)
,
1
3
1
.
2
5
,
1
4
7
.
0
8
,
1
5
2
.
7
8
,
1
5
3
.
3
0
,
1
5
3
.
9
8
,
1
6
2
.
0
0
(
8
)
.
III. RESULTS AND DISCUSSIONS
3.1.0. Thermal behavior and texture observation
T
h
t
S
e
l
e
e
h
C
p
h
p
a
m
i
o
a
y
n
m
n
c
s
c
d
e
h
t
a
r
n
e
z
a
g
n
e
r
d
s
s
e
i
t
w
u
n
o
h
i
o
e
l
n
r
t
T
e
S
t
e
t
m
p
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e
1
M
m
e
e
s
.
r
d
e
a
t
u
o
h
S
o
u
r
e
n
d
o
a
a
s
g
a
d
s
w
e
e
g
t
e
a
l
n
l
a
s
l
d
r
a
r
t
s
s
e
y
e
h
e
n
c
w
i
n
p
n
h
a
g
c
s
e
c
o
b
t
r
o
n
e
e
a
a
r
g
r
n
s
i
e
c
t
i
t
o
r
n
o
a s
o
n
y
s
n
e
n
a
l
e
s
u
d
s
i
n
e
i
f
f
e
r
t
i
a
c
a
i
n
a
l
i
m
(
D
)
t
h
s
i
c
t
o
f
t
h
c
T
h
e
a
c
n
o
t
i
n
a
n
e
s
d
o
n
d
o
o
t
e
l
i
s
d
a
a
r
s
u
a
r
i
e
a
b
l
O
e
P
A
p
t
i
a
l
e
x
X
r
t
u
e
r
e
s
m
s
v
e
p
o
a
d
r
i
z
g
o
m
f
i
c
r
o
s
p
e
(
m
)
.
e
m
p
l
l
a
g
l
-
r
f
f
r
a
t
c
o
t
r
y
p
w
e
u
s
t
n
i
r
m
s
h
s
e
f
e
p
s
e
t
a
i
v
m
l
f
t
t
h
e
n
l
e
c
s
u
v
o
m
p
n
g
s
o
s
u
n
a
n
b
d
n
s
d
a
.
T
t
a
h
y
s
b
e
l
e
n
h
l
1
a
s
u
r
e
r
m
e
s
o
m
o
a
f
r
t
t
t
i
z
h
e
m
e
e
s
t
m
h
e
a
r
e
s
s
a
d
a
h
t
r
t
a
a
a
.
r
e
s
s
h
l
a
o
t
t
i
f
n
g
t
e
o
t
c
h
o
e
m
m
m
t
p
a
o
h
o
t
g
e
u
e
r
r
n
r
a
m
d
a
l
r
a
i
t
i
o
t
u
o
p
s
e
t
h
s
;
s
s
i
n
c
r
d
e
i
n
e
a
t
h
l
p
c
a
a
s
n
g
o
f
h
e
p
h
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r
e
n
T
i
e
i
o
n
S
s
C
.
A
t
l
l
i
a
l
a
r
y
t
l
e
c
r
y
t
a
t
o
m
p
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t
u
D
h
e
r
m
s
h
o
w
t
w
o
e
x
o
t
h
e
r
m
a
l
t
r
a
n
s
i
t
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n
s
o
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e
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t
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r
o
p
i
c
l
i
q
u
i
d
a
n
d

1
4
0
/
[
8
8
2
]
A. A. Salisu et al.
TABLE 1
P
h
a
s
e
T
r
a
n
s
i
t
i
o
n
T
e
m
p
e
r
a
t
u
r
e
s
a
n
d
E
n
t
h
a
l
p
i
e
s
O
b
t
a
i
n
e
d
f
r
o
m
D
S
C
S
c
a
n
s
T
r
i
a
o
n
n
s
e
i
t
n
i
o
n
a
t
l
e
p
m
p
s
e
v
r
a
a
l
t
u
u
e
r
s
e
( T=ꢁC)
( DH=JKꢂ1
a
n
)
d
,
a
h
s
e
s
a
o
t
c
i
a
g=
t
e
c
d
o
C
o
m
p
o
u
n
d
T
r
a
n
s
i
t
t
h
i
e
i
n
o
l
i
n
g
BA.O3O.3
BA.O4O.3
BA.O5O.3
BA.O6O.3
BA.O8O.3
C
I
C
I
C
I
C
I
r
1
r
1
r
1
r
1
r
1
1
1
.
2
.
8
.
6
.
5
5
2
3
.
1
.
6
4
2
(
.
(
.
3
2
4
4
6
2
8
2
.
)
.
)
)
)
)
)
4
S
2
S
)
S
m
S
m
m
m
m
m
m
A
m
A
A
C
A
C
A
1
2
2
7
(
.
1
5
2
1
.
(
4
1
.
6
r
)
I
I
0
9
(
0
8
A
9
1
9
7
.
)
C
1
6
5
)
1
3
8
.
4
6
(
0
.
3
)
2
6
(
0
2
.
8
7
4
1
6
3
1
4
(
9
.
(
.
(
.
9
.
5
)
8
)
3
)
0
5
C
)
S
)
S
.
)
r
S
9
.
5
8
(
3
.
S
1
.
2
6
1
.
m
A
m
A
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r
C
4
C
4
1
2
6
4
2
.
2
4
0
(
.
1
2
.
)
8
C
)
r
I
I
2
1
2
3
(
1
.
S
S
3
S
6
.
9
(
0
2
m
8
.
(
1
9
.
3
5
(
2
.
S
1
1
.
8
5
2
.
S
1
3
1
.
6
9
(
1
.
7
)
2
8
8
0
6
2
.
6
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2
.
(
.
9
A
9
4
.
5
6
8
(
0
3
(
3
m
3
C
8
.
8
4
(
9
.
4
)
C
r
C
I
1
2
.
3
4
4
4
.
)
)
S
m
m
A
1
.
1
)
3
3
(
0
0
.
(
7
A
b
T
b
r
r
a
e
n
v
s
i
i
a
t
t
i
i
o
o
n
n
s
e
:
n
C
r
¼
c
r
y
s
s
i
t
n
a
l
p
;
S
m
n
A ¼
s
m
e
c
t
i
c
A
;
S
m
C
¼
S
m
e
c
t
i
c
C
;
I
¼
i
s
o
t
r
o
p
i
c
p
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a
s
e
a
n
d
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h
a
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s
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h
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c
e
t
d
r
a
r
1
a
n
a
2
n
s
e
t
.
i
n
e
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t
i
a
i
o
n
z
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n
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d
o
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n
o
c
o
o
b
l
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f
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h
o
n
a
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g
v
m
n
c
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r
c
f
n
0
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n
d
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t
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p
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h
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a
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d
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2 ꢁ
o
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n
g
o
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v
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d
u
n
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e
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p
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t
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O
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r
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a
d
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n
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n
g
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n
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r
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r
g
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h
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d
l
o
k
n
y
l
s
p
e
a
c
D
e
S
r
t
C
o
C
i
r
n BA.O4O.3
m o g r a p h d u r i n g
,
t
w
o
4
t
h
h
e
e
r
m
i
t
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o
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t
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t
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t
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n
o
o
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i
n
c
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c
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r
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c
t
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y
.
T
e
a
x
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u
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r
t
e
h
o
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b
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e
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r
v
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x
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n
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p
r
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n
s
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c
s
d
g
s
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u
(
r
1
2
i
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5
g
h
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t
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a
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c
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l
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p
n
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g
c
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g
c
p
c
,
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h
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r
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d
h
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n
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a
o
s
p
d
h
p
a
e
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a
p
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s
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r
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r
e
d
l
y
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v
a
s
s
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e
b
o
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s
n
e
r
c
.
h
v
o
e
o
d
l
o
n
n
g
e
a
.
2 ꢁ
i
s
t
r
e
e
r
c
i
p
r
o
(
1
.
8 ꢁ
)
h
e
t
r
s
a
e
s
r
i
s
o
e
w
r
r
o
p
q
h
d
,
s
p
i
v
l
y
m
e
A
F
z
f
g
d
l
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p
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n
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c
r
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o
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t
c
a
l
l
y
t
o
m
u n t i l
o
e
-
t
r
o
c
s
e
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e
u
r
2
2
T
h
a
s
n
a
d
i
t
i
n
l
p
h
a
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t
r
a
n
s
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n
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t
t
a
l
l
i
a
9
.
8
4 ꢁ
C
.
W
e
h
l
a
a
v
r
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w
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c
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h
n
t
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2
1
]
f
u
r
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g
t
n
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5
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a
s
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.
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3
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h
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r
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3
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s
5

Novel Non-Symmetric Liquid Crystal
1
4
1
/
[
8
8
3
]
FIGURE 1
BA.O8O.3.
R
t
e
p
r
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Novel Non-Symmetric Liquid Crystal
1
4
3
/
[
8
8
5
]
FIGURE 4
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