ISSN 1070-3632, Russian Journal of General Chemistry, 2006, Vol. 76, No. 3, p. 498.
Pleiades Publishing, Inc., 2006.
Original Russian Text V.V. Zuev, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 3, p. 524.
LETTERS
TO THE EDITOR
4
-Allyloxy-4 -cyanobiphenyl.
A Photoluminescing Nematic Liquid Crystalline Compound
V. V. Zuev
Institute of High-Molecular Compounds, Russian Academy of Sciences,
Bol’shoi pr. 31, St. Petersburg, 199004 Russia
Received December 8, 2005
DOI: 10.1134/S1070363206030261
We made use of the Williamson reaction to syn-
thesize a photoluminescing nematic liquid crystalline
compound 4-allyloxy-4 -cyanobiphenyl. The com-
pound strongly luminesces in dioxane solution in the
spectrum (CDCl ), , ppm (J, Hz): 4.59 d (OCH , J
3 2
5.16), 5.32 d (=CH , cis, J 10.28), 5.44 d (=CH ,
2
2
trans, J 17.65), 6.02 6.12 m (=CH), 7.01 d (ortho,
J 8.84), 7.52 d (meta, J 8.84), 7.63 d (meta, J 8.84),
7.68 d (ortho, J 8.84). Found, %: C 81.45; H 5.50;
N 6.10. C H NO. Calculated, %: C 81.68; H 5.57;
blue range at
15 nm ( 7000). The luminescence intensity com-
pares with that of anthracene. Nematic range 58 81 C
mp 58 C, clearing point 81 C, nematic isotropic
418 nm and absorbs at
max
max
3
1
6
13
N 5.95.
(
transition). The temperature ranges differ only slightly
from those for an analog, 4-cyano-4 -propylbiphenyl
The IR spectrum was obtained on a Bruker Vertex
instrument. The H NMR spectrum was recorded on a
1
(
63.5 75 C [1]).
Bruker MSL-400 spectrometer (400 MHz). The UV
spectrum was registered in a 1 10 5 M dioxane solu-
Thus, we are the first to obtain a nematic com-
pound of the cyanobiphenyl series with a strong
photoluminescence in the blue range.
tion on a Specord M-40 spectrophotometer. The
5
luminescence spectrum was obtained in a 1 10
M
dioxane solution on an LS-100-3 spectrofluorimeter
(PTI-Canada). The phase transition temperatures were
measured on a Boetius hot stage.
4
-Allyloxy-4 -cyanobiphenyl. A mixture of 1 g of
4
3
-cyano-4‘-hydroxybiphenyl, 1.3 ml of allyl bromide,
g of potash, and 30 ml of DMF was stirred for 5 h
at 160 C and then cooled and poured into 250 ml of
water. The precipitate that formed was filtered off and
recrystallized from ethanol. Yield 1.1 g (96%). IR
REFERENCES
1. Khimicheskie reaktivy i vysokochistye khimicheskie
veshchestva: Katalog (Chemical Reagents and High-
Purity Chemical Sunstances: Catalog), Moscow:
Khimiya, 1990, p. 589.
1
spectrum (KBr), , cm : 3042, 3018, 2959, 2894,
2
1
856, 2782, 2172.5 (CN), 1603, 1578, 1555, 1493,
455, 1291, 1251, 1215, 995, 937, 842. H NMR
1
498
Zuev
