Synthesis of push-pull chromophores including an N-[4-(4-methoxyphenoxy)butyl]carbazole fragment

Full text of DOI:10.1134/S1070428015050267

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2015, Vol. 51, No. 5, pp. 735–739. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © D.G. Selivanova, O.A. Maiorova, E.V. Shklyaeva, G.G. Abashev, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51,
No. 5, pp. 751–755.
SHORT
COMMUNICATIONS
Synthesis of push-pull Chromophores Including
an N-[4-(4-Methoxyphenoxy)butyl]carbazole Fragment
a
a
b,c
a,c
D. G. Selivanova , O. A. Maiorova , E. V. Shklyaeva , and G. G. Abashev
a
Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences,
ul. Akademika Koroleva 3, Perm, 614013 Russia
e-mail: gabashev@psu.ru
b
Institute of Natural Sciences at Perm State National Research University, Perm, Russia
c
Perm State National Research University, Perm, Russia
Received January 26, 2015
DOI: 10.1134/S1070428015050267
Organic substances with nonlinear optical proper-
ties of the second order are the promising materials for
molecular electronics and photonics, that is, finally, for
telecommunication and electro optical devices [1–6].
These materials possess some advantages if compared
with their inorganic analogs: they have high values of
nonresonance susceptibility, high nonlinear optic
response, high transmissibility, low dielectric permitti-
vity, besides they are sufficiently easy to process and
economic [1, 7]. However certain drawbacks in their
practical application also exist, e.g., the strong
intermolecular electrostatic interaction, poor solubility
in common organic solvents, thermal and
photochemical instability. By altering the chemical
structure of material, namely, by selecting the
optimum electron-donor and electron-acceptor
substituents it is possible to obtain the maximum
nonlinearity on the molecular level and also affect the
chemical, photochemical, and thermal stability. The
introduction of electron-donor ortho- or para-alkoxy-
phenyl groups into the monomers is known to change
the optical properties of chromophores. It results in
increasing of the electro optic coefficient value (r )
In this work we continued to study carbazole-
containing compounds including in their structure ω-
(4-methoxyphenyl)alkyl substituents at the nitrogen
atom of this heterocycle [12, 13] and have synthesized
two new chromophores 8 and 9 including N-[4-(4-
methoxyphenoxy)butyl]carbazole moiety as a donor
fragment. The optical and electrochemical properties
of all prepared during thes work compounds were
examined. First from the corresponding α,ω-
dibromoalkane and p-methoxyphenol 1 in acetone the
starting bromides 2 and 3 were prepared [12]. The
subsequent alkylation of carbazole with the syn-
thesized bromides under the conditions of the phase-
transfer catalysis in the system acetone–16 M water
solution of NaОН–benzyltriethylammonium chloride
led to the formation of the corresponding N-substituted
carbazoles 4 and 5 [13]. The acetylation of the latter at
room temperature in dichloroethane in the presence of
SnCl afforded 3-acetylcarbazoles 6 and 7.
4
Further under the Knoevenagel condensation
conditions acetylcarbazole 6 was treated with malono-
dinitrile or ethyl cyanoacetate in benzene media in the
presence of a catalytic amount of ammonium acetate to
obtain chromophores 8 and 9 – yellow viscous oils,
well soluble in alcohols, alkanes, and haloalkanes.
3
3
and molecular hyperpolarizability β [8–10]. When
such a group is situated in the peripheral part of a long
aliphatic chain and is incorporated into the chromo-
phore structure both intermolecular and intramolecular
interaction may occur between the donor and acceptor
parts of the chromophore. Besides, the introduction of
long-chain substituents in the structure of compounds
affects the character of their packing in the solid state
and their thermal stability [11].
UV and fluorescence spectra of compounds 6–9
were measured in chloroform. From the data of
absorption and emission spectra the Stokes shifts were
estimated (Δλ): 110 (6), 98 (7), 121 (8), 153 (9) nm.
On the basis of the longest absorption wavelength
opt
g
value (λonset) the width of the forbidden bandgap (E )
7
35

7
36
SELIVANOVA et al.
,
N
H
OMe
OMe
Br(CH ) Br, Δ
BnEt NCl, Δ
2
n
3
N
(CH2)n
O
Me CO, KOH
Me CO, 50% NaOH
2
2
OMe
HO
O(CH ) Br
2
n
1
2, 3
4, 5
R
CN
Me
Ac
N
n = 4
N
CH RCN, Δ ,
2
(CH2)n
(CH )
2 n
AcBr, SnCl4
CH Cl2
AcONH
4
, AcOH
O
O
C
H
6 6
2
OMe
OMe
6
, 7
8, 9
n = 4 (2, 4, 6, 8, 9), 6 (3, 5, 7); R = CN (8), COOEt (9).
was calculated [14]: 3.02 (6), 3.18 (7), 2.61 (8),
contrast to compound 4 only one reduction peak is
pbserved at 1095 mV (Ered) which corresponds to Eox.
1
1
2
.69 (9) eV.
In both cases at each succeeding cycle the current
value increases, and on the surface of the working elec-
trode grows the blue film of the respective polymer [13].
The electrochemical properties of compounds syn-
thesized were explored by cyclic voltammetry. The cyclic
voltammograms of compound 4 exhibit three oxidation
1
ox
2
ox
peaks are present, at 910 (E ), 1235 (E ), and 1330
The incorporation of electron-acceptor withdrawing
groups into the structure of carbazoles 4 and 5 changes
the pattern of the electrochemical oxidation and leads
3
(
(
E ) mV. Two reduction waves at 885 and 1140 mV
ox
1
2
red
E
and E ) correspond to the first and to the second
red
1
2
oxidation potentials – E and E . Analogous pattern
ox
ox
was observed for compound 5. Three oxidation peaks
are clearly seen (1020, 1215 and 1320 mV), but in
1
1
20
00
6
8
9
1
1
1
1
8
6
4
60
40
20
00
0
0
0
80
60
40
20
0
2
0
0
20
–20
2
00 400 600 800 10001200140016001800
E, mV
–
5
00
1000
E, mV
1500
Fig. 2. Cyclic voltvoltammogram of compound 6, 8, 9,
glassy carbon disk, Et
(9 : 1). 6: E
1265 mV. 9: E
Fig. 1. Cyclic voltvoltammogram of compound 6, glassy
carbon disk, 10 cycles, Et
NClO
, Vscan 50 mV/s, CH
CN–CH
Cl
с
4
4
3
2
2
1
a
1
1
2
1
4
NClO
4
, Vscan 50 mV/s, CH
3
CN–
1340, E
с
1270 mV. 8: E
a
1295, E
a
1380, E
1
a
1
1
1
CH
2
Cl
2
(9 : 1). E
1340, E
с
1270 mV.
с
1295, E 1265 mV.
a
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 5 2015

SYNTHESIS OF PUSH-PULL CHROMOPHORES INCLUDING
737
to the growth of the values of redox potentials. The
only one clear reversible oxidation peak was observed
in the cyclic voltammograms of compounds 6, 8 and 9
at 1340 (6), 1295 (8), and 1295 (9) mV; the correspon-
ding reduction peaks had blurred forms and appeared
in the region 1260–1270 mV. The replacement of the
carbonyl group by a vinyl fragment containing two
strong electron-acceptor substituents results in a slight
decrease in the oxidation potentials. In all cases at each
succeeding cycle the current value increases, and on
the surface of the working electrode grows the blue
film of the respective polymer, consequently, the
polymerization occurs at the positions 2 and 7 of the
carbazole ring [15]. Examples of cyclic voltammo-
grams of chromophores 6, 8 and 9 are presented in
Figs. 1, 2 (working electrode – glassy carbon disk).
purification by column chromatography on silica gel
was also possible (eluent acetone–hexane, 1 : 2).
9
-[4-(4-Methoxyphenoxy)butyl]-9H-carbazole
1
(
4). Yield 75%, mp 71–72°С (70–72°C [13]). Н NMR
spectrum, δ, ppm: 1.81 quintet (2Н, CH СН N, J
2
2
6
.3 Hz), 2.07 quintet (2Н, OСН CH , J 6.9 Hz), 3.74 s
2 2
(
3Н, ОMe), 3.88 t (2Н, NCH , J 6.3 Hz), 4.38 t (2Н,
2
ОCH , J 6.9 Hz), 6.79 s (4Н, C H ), 7.23 d (2Н,
2
6
4
carbazole, J 6.3 Hz), 7.39–7.48 m (4Н, carbazole),
8
.09 d (2Н, carbazole, J 7.8 Hz).
9-[6-(4-Methoxyphenoxy)hexyl]-9H-carbazole
1
(5). Yield 70%, mp 69–70°С (70–71°C [13]). Н NMR
spectrum, δ, ppm: 1.35–1.39 m (4H, OCH
CH ·
2
2
CH
6.9 Hz), 1.79 quintet (2Н, OСН
3Н, ОMe), 3.81 t (2Н, NCH , J 6.3 Hz), 4.39 t (2Н,
CH
CH
CH
N), 1.60 quintet (2Н, CH
СН
N, J
2
2
2
2
2
2
CH
, J 6.9 Hz), 3.67 s
2
2
(
2
1-(ω-Bromoalkoxy)-4-methoxybenzenes (2 and 3).
ОCH , J 6.9 Hz), 6.79 s (4Н, C H ), 7.18 t (2Н,
2
6
4
To a solution of 0.1 mol of p-methoxyphenol 1 in 200 mL
of acetone was added 6.72 g (0.12 mol) of KОН, after
its dissolution 23.7 mL (0.2 mol) of 1,4-dibro-
mobutane or 30.8 mL (0.2 mol) of 1,6-dibro-mohexabe
was added dropwise, the mixture was refluxed for 1 h,
cooled, the resulted precipitate (products of
dimerization) was filtered off. The filtrate was
evaporated, the residue was recrystallized from EtOH.
carbazole, J 7.5 Hz), 7.44 t (2Н, carbazole, J 7.5 Hz),
7
7
.59 d (2Н, carbazole, J 8.1 Hz), 8.14 (2Н, carbazole, J
.5 Hz).
Carbazoles (6 and 7). To a solution of 0.03 mol of
carbazole 4 or 5 in 60 mL of anhydrous CH
added 7.0 mL (0.06 mol) of SnCl , the mixture was
stirred for 10 min, then was added dropwise 2.2 mL
0.03 mol) of acetyl bromide. The reaction mixture
Cl was
2
2
4
(
1
-(4-Bromobutoxy)-4-methoxybenzene (2). Yield
was stirred for 24 h at room temperature, poured in the
mixture of ice and hydrochloric acid, extracted with
dichloromethane, the combined organic solutions were
washed with water till neutral reaction, and
evaporated. The solid residue was purified by column
chromatography on silica gel (eluent dichloromethane–
hexane, 1 : 1).
1
6
8%, mp 43–45°C (46–47°C [16, 17]). Н NMR spec-
trum, δ, ppm: 1.90 quintet (2Н, CH СН Br, J 6.6 Hz),
2
2
2
.05 quintet (2Н, OСН CH , J 6.3 Hz), 3.47 t (2Н,
2 2
СН Br, J 6.3 Hz), 3.75 s (3Н, ОMe), 3.93 t (2Н,
2
ОСН , J 6.3 Hz), 6.81 s (4Н, C H ).
2
6
4
1
-[6-Bromohexyloxy]-4-methoxybenzene (3).
1
Yield 65%, mp 48–49°C [18]. Н NMR spectrum, δ,
ppm: 1.43–1.47 m (4H, OCH CH СH CH CH CH ·
3
-Acetyl-9-[4-(4-methoxyphenoxy)butyl]-9H-
2
2
2
2
2
2
carbazole (6). Yield 85%, gray crystals, mp 77–78°C.
Br), 1.72 quintet (2Н, CH СН Br, J 6.6 Hz), 1.87
–1
2
2
IR spectrum, ν, cm : 1626 (C=O). UV absorption
quintet (2Н, OСН CH , J 6.3 Hz), 3.40 t (2Н, СН Br, J
2
2
2
spectrum, λmax, nm (log ε): 322 (3.79), 330 (3.78);
fluorescence spectrum, λmax, nm: 388, 424, 440. Stokes
6
6
.9 Hz), 3.74 s (3Н, ОMe), 3.83 t (2Н, ОСН , J 6.3 Hz),
2
.76 s (4Н, C H ).
1
6
4
shift ∆λ 110 nm. Н NMR spectrum, δ, ppm: 1.81
9
-[ω-(4-Methoxyphenoxy)alkyl]-9H-carbazoles
4 and 5). To a solution of 0.024 mol of carbazole and
.024 mol of bromoalkoxybenzene 2 or 3 in 80 mL of
acetone was added 0.02 g of BnEt NCl and 20 mL of
quintet (2Н, CH
2 2
СН N, J 6.3 Hz), 2.08 quintet (2Н,
(
0
OСН CH , J 7.2 Hz), 2.71 s (3H, COCH ), 3.74 s (3Н,
2
2
3
ОMe), 3.89 t (2Н, NCH , J 6.0 Hz), 4.40 t (2Н, ОCH ,
2 2
J 7.2 Hz), 6.78 s (4Н, C H ), 7.29 t (1H, carbazole, J
3
6
4
1
6 M water solution of NaOH, the mixture was
7.8 Hz), 7.39–7.53 m (3H, carbazole), 8.10 d (1H,
refluxed for 12 h, cooled, the organic layer was
separated, poured into 200 mL of water, and extracted
with dichloromethane (3 × 50 mL). The combined or-
ganic extracts were washed with water (2 × 100 mL),
carbazole, J 6.9 Hz), 8.14 d (1H, carbazole, J 7.8 Hz), 8.73
s (1H, carbazole). Mass spectrum, m/z (I , %): 388
rel
+
+
(8.1) [M + H] , 387 (28.3) [M] , 265 (13.8), 264 (67.9),
223 (16.1), 222 (100), 180 (24.9), 179 (23.2), 43 (16.1).
Found, %: C 77.38; H 6.55; N 3.51. C H NO .
dried with MgSO . The solvent was removed, the
4
25 25
3
residue was recrystallized from methanol; the
Calculated, %: C 77.49; H 6.50; N 3.61. M 387.48.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 5 2015

7
38
SELIVANOVA et al.
3
-Acetyl-9-[6-(4-methoxyphenoxy)hexyl]-9H-
Ethyl 2-cyano-3-{9-[4-(4-methoxyphenoxy)-
carbazole (7). Yield 80%, gray crystalline substance,
mp 88–89°C. UV absorption spectrum, λmax, nm (log ε):
butyl]-9H-carbazol-3-yl}but-2-enoate (9). Yield
–
1
75%, yellow viscous substance. IR spectrum, ν, cm :
2259 (C≡N), 1722 (COOEt). UV absorption spectrum,
λmax, nm (log ε): 320 (3.45), 351 (3.47), 373 (3.51),
397 (3.37); fluorescence spectrum, λmax, nm: 446, 550.
3
3
20 (3.69), 330 (3.67); fluorescence spectrum, λmax, nm:
78, 410, 428. Stokes shift ∆λ 98 nm. Н NMR spec-
1
trum, δ, ppm: 1.45–1.49 m (4H, OCH CH CH CH ·
2
2
2
2
1
CH CH N), 1.69 quintet (2Н, CH СН N, J 6.3 Hz), 1.91
Stokes shift ∆λ 153 nm. Н NMR spectrum, δ, ppm:
2
2
2
2
quintet (2Н, OСН CH , J 7.2 Hz), 2.72 s (3H, COCH ),
1.39 t (3H, COOCH CH , J 6.9 Hz), 1.85 quintet (2Н,
2
2
3
2
3
3
.75 s (3Н, ОMe), 3.84 t (2Н, NCH , J 6.3 Hz), 4.33 t
СН СН N, J 6.3 Hz), 2.10 quintet (2Н, OСН СН , J
2
2 2 2 2
(
2Н, ОCH , J 6.9 Hz), 6.79 s (4Н, C H ), 7.29 t (1H, car-
7.2 Hz), 2.83 s (3H, Me), 3.75 s (3Н, ОMe), 3.91 t
(2Н, NСН , J 6.0 Hz), 4.36 t (2Н, ОСН , J 7.5 Hz),
2
6
4
bazole, J 7.2 Hz), 7.38–7.51 m (3H, carbazole), 8.11 d
1H, carbazole, J 8.4 Hz), 8.15 d (1H, carbazole, J 7.8 Hz),
2
2
(
4.39 q (2H, COOСН CH ), 6.80 s (4H, C H ), 7.26 t
2 3 6 4
8
.74 s (1H, carbazole). Mass spectrum, m/z (I , %):
(1H, carbazole, J 7.8 Hz), 7.42–7.52 m (3H,
carbazole), 7.63 d (1H, carbazole, J 7.5 Hz), 8.10 d
(1H, carbazole, J 7.8 Hz), 8.25 s (1H, carbazole). С,
δ, ppm: 14.2, 23.8, 25.9, 27.0, 29.7, 43.0, 55.6, 55.7,
61.8, 68.1, 108.6, 109.1, 114.6, 114.7, 115.4, 117.4,
rel
+
+
416 (15.4) [M + H] , 415 (48.9) [M] , 223 (17.1), 222
1
3
(
100), 180 (23.5), 179 (23.4), 124 (13.5), 43 (11.6).
Found, %: C 77.87; H 6.98; N 3.21. C H NO .
Calculated, %: C 78.04; H 7.03; N 3.37. M 415.52.
27
29
3
1
1
19.8, 120.4, 120.6, 122.7, 122.9, 125.6, 126.4, 126.5,
Chromophores (8 and 9). General procedure. A
mixture of 5 mmol of carbazole 6, 0.5 mL (5 mmol) of
ethyl cyanoacetate or 0.3 g (5 mmol) of malonodinit-
rile, 1.14 mL of acetic acid, and 0.4 g of ammonium
acetate in 50 mL of benzene was refluxed for 10 h with
a Dean-Stark trap, then 0.5 mL (5 mmol) of NCCH2·
COOEt or 0.3 g (5 mmol) of CH (CN) , 1.14 mL of
30.6, 140.9, 141.6, 152.9, 153.8, 163.0. Mass
+
spectrum, m/z (I , %): 483 (10.4) [M + H] , 482 (29.6)
rel
+
[
3
(
M] , 360 (27.1), 359 (100), 318 (10.1), 317 (41.6),
14 (16.9), 313 (68.4), 289 (17.4), 271 (15.7), 243
12.7), 242 (10.7), 241 (10.4), 229 (17.6). Found, %: C
7
7
4.56; H 6.21; N 5.70. C H N O . Calculated, %: C
30 30 2 4
2
2
4.67; H 6.27; N 5.81. M 482.57.
AcOH, and 0.4 g of AcONH was added. The reaction
4
1
mixture was again boiled for 10 h, cooled, washed
Н NMR spectra were registered on a spectrometer
with water, the organic layer was dried with Na SO ,
2
4
Varian Mercury plus-300 in CDCl (internal reference
3
evaporated, the residue was purified by column
chromatography on silica gel (elient CH Cl ).
HMDS), mass spectra were measured on an instrument
Agilent Technologies 6890N/5975B (ionizing
electrons energy 70 eV). IR spectra were recorded on a
spectrophotometer Specord 75 IR from solutions in
chloroform. Elemental analysis was carried out on an
analyzer CHNS-932 LECO Corp. UV spectra were
obtained on a spectrophotometer SF-2000 in chloro-
form, cell 10 mm. Fluorescence spectra were register-
red on a spectrofluorimeter Shimadzu RF-5301. The
excitation wavelength 220 nm, cell size 10 × 10 mm,
2
2
2
-(1-{9-[4-(4-Methoxyphenoxy)butyl]-9H-carba-
zol-3-yl}ethylidene)malonodinitrile (8). Yield 70%,
–
1
yellow viscous substance. IR spectrum, ν, cm : 2217
(
(
(
5
1
C≡N). UV absorption spectrum, λmax, nm (log ε): 322
3.79), 336 (3.78), 356 (3.77), 379 (3.77), 392 (3.74), 407
3.66), 421 (3.66); fluorescence spectrum, λmax, nm: 458,
1
42. Stokes shift ∆λ 121 nm. Н NMR spectrum, δ, ppm:
.83 quintet (2Н, СН СН N, J 6.3 Hz), 2.09 quintet (2Н,
2
2
OСН СН , J 7.2 Hz), 2.76 s (3H, Me), 3.75 s (3Н,
solvent CHCl . The reaction progress was monitored
3
2
2
ОMe), 3.92 t (2Н, NСН , J 6.0 Hz), 4.42 t (2Н, ОСН ,
and the purity of compounds obtained was checked by
TLC on Sorbfil plates. The mixtures were separated
and the target products were purified by column
chromatography on silica gel (Lancaster, Silica gel 60,
0.060–0.2 mm). Electrochemical measurements were
2
2
J 6.9 Hz), 6.79 s (4H, C H ), 7.31 t (1H, carbazole, J
6
4
7
.5 Hz), 7.45–7.55 m (3H, carbazole), 7.77 d (1H, carba-
zole, J 8.4 Hz), 8.12 d (1H, carbazole, J 7.5 Hz), 8.39 s
1
3
(
1H, carbazole). С NMR spectrum, δ, ppm: 14.2,
–3
2
1
1
1
3.7, 25.9, 26.9, 28.9, 38.7, 43.2, 55.7, 68.1, 109.0,
09.4, 113.9, 114.7, 115.4, 120.4, 120.8, 120.9, 122.6,
23.2, 125.6, 126.2, 127.0, 128.8, 130.8, 141.1, 142.6,
carried out in monomer solutions (с 10 mol/L) in 9 : 1
acetonitrile–CH Cl mixture, at room temperature using
as supporting electrolyte (с 0.1 mol/L). A
2
2
+
–
Et N ClO
4 4
52.9, 153.9. Mass spectrum, m/z (I , %): 435 (15.4)
potentiostate P-8 was used with electrochemical sensor
Module ЕM-04 and three-electrode electrochemical
cell: working electrode – glassy carbon disc, ITO-
plate, or Pt wire, auxiliary electrode – Pt wire and Ag/
rel
+
[M] , 313 (23.5), 312 (100), 271 (12.1), 270 (52.8).
Found, %: C 77.18; H 5.70; N 9.51. C H N O .
2
8
25
3
2
Calculated, %: C 77.22; H 5.79; N 9.65. M 435.52.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 5 2015

SYNTHESIS OF PUSH-PULL CHROMOPHORES INCLUDING
739
AgCl reference electrode. The measurements were
performed at room temperature, potential scanning rate
Vscan 50 mV/s.
8. Cheng, Y.-J., Luo, J., Hau, S., Bale, D.H., Kim, T.-D.,
Shi, Z., Lao, D.B., Tucker, N.M., Tian, Y., Dalton, L.R.,
Reid, P.J., and Jen, A.K-Y., Chem. Mater., 2007, vol. 19,
p. 1154.
The study was carried out under the financial
support of the Russian Foundation for Basic Research
9
. Davies, J.A., Elangovan, A., Sullivan, P.A., Olbricht, B.C.,
Bale, D.H., Ewy, T.R., Isborn, C.M., Eichinger, B.E.,
Robinson, B.H., Reid, P.J., Li, X., and Dalton, L.R.,
J. Am. Chem. Soc., 2008, vol. 130, p. 10565.
(
grants nos. 14-03-00341а, 14-03-96003 r_Ural_а) and
of the Ministry of Education and Science of the
Russian Federation.
10. Wu, J., Wilson, B.A., Smith, D.W., and Nielsen, S.O.,
J. Mater. Chem. C., 2014, vol. 2, p. 2591.
REFERENCES
11. Jin, J.-I., Park, C.-K., and Shim, H.-K., Polymer, 1994,
vol. 35, p. 480.
1
. Nelineinye Opticheskie Svoistva Organicheskikh
Molekul i Crystallov, Shemla, D., and Ziss, Zh., Eds.,
Moscow: Mir, 1989, vol. 1.
12. Abashev, G.G., Galkin, A.V., Syutkin, R.V., Usatykh, V.A.,
and Shklyaeva, E.V., Innovatsionnyi potentsial estest-
vennyakh nauk. Trudy Mezhdunarondoi nauchnoi
konferentsii, Perm, 2006, vol. 1, p. 133.
13. Syutkin, R.V., Abashev, G.G., and Shklyaeva, E.V.,
Butlerov soobshch., 2008, vol. 13, p. 11.
14. Meng, H., Zheng, J., Lovinger, A.J., Wang, B.-C.,
Van Patten, P.G., and Bao, Z., Chem. Mater., 2003, vol. 15,
p. 1778.
15. Data, P., Pander, P., Lapkowski, M., Swist, A.,
Soloducho, J., Reghu, R.R., and Grazulevicius, J.V.,
Electrochim. Acta., 2014, vol. 128, p. 430.
2
3
4
. Kajzar, F., Lee, K.S., and Jen, A.K.Y., Adv. Polymer.
Sci., 2003, vol. 161, p. 1.
. Marder, S.R., Kippelen, B., Jen, A.K.Y., and
Peyghambarian, N., Nature, 1997, vol. 388, p. 845.
. Dalton, L.R., Steier, W.H., Robinson, B.H., Zhang, C.,
Ren, A., Garner, S., Chen, A.T., Londergan, T., Irwin, L.,
Carlson, B., Fifield, L., Phelan, G., Kincaid, C., Amend, J.,
and Jen, A., J. Mater. Chem., 1999, vol. 9, p. 1905.
5
. Block, B.A., Younkin, T.R., Davids, P.S., Reshotko, M.R.,
Chang, P., Polishak, B.M., Huang, S., Luo, J.,
and Jen, A.K.Y., Opt. Express, 2008, vol. 16,
p. 1832.
16. Yu, X.-F., Lu, S., Ye, C., Li, T., Liu, T., Liu, S., Fan, Q.,
Chen, E.-Q., and Huang, W., Macromolecules, 2006,
vol. 39, p. 1364.
6
. Dushenko, G.A., Mikhailova, O.I., Starikov, D.A., and
Mikhailov, I.E., Vestn. Yuzhn. Nauch. Tsentra Akad.
Nauk, 2007, vol. 3, p. 26.
17. Li, Y., Li, G., Wang, X., Lin, C., Zhang, Y., and Ju, Y.,
Chem. Eur. J., 2008, vol. 14, p. 10331.
1
8. Zhang, Z.-J., Zheng, Z., Qiang, L.-L., Ma, Z., Xie, S.-X.,
Peng, B., Huang, W., and Wei, W., Macromol. Rapid
Commun., 2006, vol. 27, p. 1317.
7. Liu, J., Hou, W., Feng, S., Qiu, L., Liu, X., and Zhen, Z.,
J. Phys. Org. Chem., 2011, vol. 24, p. 439.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 5 2015