Synthesis of novel T-type polyurethanes containing 2,5-dioxynitrostilbenyl group as a NLO chromophore and their properties

Article abstract of DOI:10.1080/15421400490506621

2,5-Di-(2′-hydroxyethoxy)-4′-nitrostilbene (2) was prepared and condensed with 2,4-toluenediisocyanate, 3,3′-dimethoxy-4,4′- biphenylenediisocyanate and 1,6-hexamethylenediisocyanate to yield novel T-type polyurethanes 3-5 containing the NLO-chromophore 2,5-dioxynitrostilbenyl group, which constitutes a part of the polymer backbone. Polymers 3-5 were soluble in common organic solvents such as acetone and DMSO. Polymers 3-5 showed a thermal stability up to 280°C in TGA thermograms with T_gs of 79-159°C in DSC thermograms. The SHG coefficients (d₃₃) of poled polymer films were around 5.4 × 10^-9 esu, and they exhibited greater thermal stabilities of dipole alignments even at 10°C higher than T _g due to the partial main chain character of the polymer structure. Copyright Taylor & Francis Inc.

Full text of DOI:10.1080/15421400490506621

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Molecular Crystals and Liquid
Crystals
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Synthesis Of Novel T-Type
Polyurethanes Containing 2,5-
Dioxynitrostilbenyl Group As
A Nlo Chromophore and Their
Properties
Ju-Yeon Lee a , Won-Jung Lee a , Eun-Ju Park a ,
Han-Bae Bang a & Chang Baek a
a Institute for Nanotechnology Applications, School
of Advanced Materials Engineering , Inje University ,
Kimhae, Korea
Published online: 18 Oct 2010.
To cite this article: Ju-Yeon Lee , Won-Jung Lee , Eun-Ju Park , Han-Bae Bang
& Chang Baek (2004) Synthesis Of Novel T-Type Polyurethanes Containing 2,5-
Dioxynitrostilbenyl Group As A Nlo Chromophore and Their Properties, Molecular
Crystals and Liquid Crystals, 425:1, 119-127, DOI: 10.1080/15421400490506621
To link to this article: http://dx.doi.org/10.1080/15421400490506621
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Mol. Cryst. Liq. Cryst., Vo l . 4 2 5 , p p . 1 1 9 =[ 3 9 7 ] – 1 2 7 =[ 4 0 5 ] , 2 0 0 4
C o p y r i g h t # Ta yl o r & F r a n c i s I n c .
I S S N : 1 5 4 2 - 1 4 0 6 p ri nt =1 5 6 3 - 5 2 8 7 o n l i n e
D O I : 1 0 . 1 0 8 0 =1 5 4 2 1 4 0 0 4 9 0 5 0 6 6 2 1
SYNTHESIS OF NOVEL T-TYPE POLYURETHANES
CONTAINING 2,5-DIOXYNITROSTILBENYL GROUP
AS A NLO CHROMOPHORE AND THEIR PROPERTIES
Ju-Yeon Lee, Won-Jung Lee, Eun-Ju Park, Han-Bae Bang,
and Chang Suk Baek
Institute for Nanotechnology Applications, School of Advanced
Materials Engineering, Inje University, 607 Obang-dong,
Kimhae 621-749, Korea
2,5-Di-(20-hydroxyethoxy)-40-nitrostilbene (2) was prepared and condensed
with 2,4-toluenediisocyanate, 3,30-dimethoxy-4,40-biphenylenediisocyanate
and 1,6-hexamethylenediisocyanate to yield novel T-type polyurethanes 3–5
containing the NLO-chromophore 2,5-dioxynitrostilbenyl group, which consti-
tutes a part of the polymer backbone. Polymers 3–5 were soluble in common
organic solvents such as acetone and DMSO. Polymers 3–5 showed a thermal
stability up to 280ꢀC in TGA thermograms with Tgs of 79–159ꢀC in DSC thermo-
grams. The SHG coefficients (d33) of poled polymer films were around
5.4 ꢁ 10ꢂ9 esu, and they exhibited greater thermal stabilities of dipole align-
ments even at 10ꢀC higher than Tg due to the partial main chain character
of the polymer structure.
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INSTRUMENTATION
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RESULTS AND DISCUSSION
Synthesis and Characterization of Polymers 3–5
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SCHEME 1 S y n t h e ti c m et h o d o f p o l ym e r 3.

Synthesis and Properties of T-type NLO Polyurethanes
1
2
3
=
[
4
0
1
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SCHEME 2 S y n t h et i c m e th o d o f p o l ym e r 4.
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r 4
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l
y
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m
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s
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( 3–5
3
0
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(
M
=
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¼
1
.
9
4
)
t
f
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.
THERMAL BEHAVIORS OF POLYMERS 3–5
T
h
d
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e
p
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o
l
M
y
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e
r
,
t
s 3–5
b
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t
i
d
m
h
n
2
L
a
d
6
s
a
d
L =
c
o
ce to n e , D M F,
i e t h y l e t h e r.
a
n
S
O
u
t
u
b
a
n
T
3–5
e
i
n
h
h
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r
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P
o
l
y
s
3
–
5
s
h
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m
a
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b
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l
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p
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A
SCHEME 3
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y
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f
p
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l
y
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e
r
5
.

1
2
4
=
[
4
0
2
]
J.-Y. Lee et al.
s 3–5
TABLE I
T
h
e
r
m
a
l
P
r
o
p
er
t
i
e
s
o
f
P
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l
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r
D e gr a d a t i o n t em p ,
ꢀC b
R
e
s
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d
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eb
,%
a
t
ꢀC
5
%
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l
o
s
s
2
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%
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l
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s
s
4
e
0
%
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l
o
s
s
8
0
0ꢀ
C
a
P
o
l
y
m
e
r
Tg
,
3
4
5
1
5
5
7
9
1
9
3
3
3
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8
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3
3
5
4
7
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4
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3
2
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4
4
1
1
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8
1
1
6
1
3
3
6
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ꢀ
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a
t
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n
g
r
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t
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f
1
0
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=
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n
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t
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e
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S
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C
9
m
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p
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f
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f
l
h
t
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p
r 5
o
l
y
i
l
m
s
e
e
m
h
r
s 3–5
u
w
e
e
o
r
e
r
i
n
r
a
g
e
o
f
1
5
9 ꢀ
s 3–4
a
s
t
r
s
i
t
o
n
y
m
c
h
l
o
w
t
h
a
n
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p
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y
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b
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y
d
r
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c
h
a
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n
i
n
t
h
e
p
o
l
y
m
e
r
b
a
c
k
b
o
n
e
.
NONLINEAR OPTICAL PROPERTIES OF POLYMERS 3–5
T
h
d
e
r
n
c
r
d
e
u
N
L
O
n
r
p
r
c
a
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f
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m
e
p
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d
r
o
m
s 3–5
r
w
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t
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n
k
p
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p
t
1
7
s 3–5
0 ꢀ
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b
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r
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,
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f
t
s 3–5
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e
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a
s

Synthesis and Properties of T-type NLO Polyurethanes
1
2
5
=
[
4
0
3
]
FIGURE 2
a
A
F
M
i
m
a
g
e
s
i
o
f
s
p
i
n
-
c
o
a
t
e
d
f
i
l
m
o
f
p
o
l
y
m
e
r
5
:
(
a
)
b
e
f
o
r
e
c
o
r
o
n
a
-
p
o
l
i
n
g
;
(
b
)
f
t
e
r
c
o
r
o
n
a
-
p
o
l
n
g
.

1
2
6=[
4
0
4
]
J.-Y. Lee et al.
TABLE II
N
o
n
l
i
n
ea
r
O
pt
i
c
a
l
P
r
o
p
e
r
t
i
e
s
o
f
P
o
l
y
me
r
s 3–5
e
s
Uc
d3 1
(
e
s
u
)
d3 3 =d3 1
a
b
b
P
o
l
y
m
e
r
km a x
(
n
m
)
d3 3
(
u
)
3
4
5
3
9 1
8 8
9 0
5
. 3 6 ꢁ
. 6 4 ꢁ
. 9 3 ꢁ
1
1
1
0 ꢂ9
0 ꢂ9
0 ꢂ9
0
0
0
.
.
.
2
1
3
5
1
1
1
.
.
.
7
3
7
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