New conjugated monomers and oligomers derived from chalcones and containing thiophene, pyrrole, and pyrimidine fragments

Article abstract of DOI:10.1134/S1070427210080239

4New hybrid systems based on a series of chalcones and containing pyrimidine, thiophene, and pyrrole fragments were synthesized, and their electrochemical properties were studied. Pleiades Publishing, Ltd., 2010.

Full text of DOI:10.1134/S1070427210080239

ISSN 1070-4272, Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 8, pp. 1444−1449. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © A.Yu. Bushueva, E.V. Shklyaeva, G.G. Abashev, 2010, published in Zhurnal Prikladnoi Khimii, 2010, Vol. 83, No. 8, pp. 1339−1343.
New Conjugated Monomers and Oligomers Derived
from Chalcones and Containing Thiophene, Pyrrole,
and Pyrimidine Fragments
A. Yu. Bushuevaa, E. V. Shklyaevab, and G. G. Abasheva,b
a Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm, Russia
b Natural Science Institute, Perm State University, Perm, Russia
Received March 10, 2010
Abstract—4New hybrid systems based on a series of chalcones and containing pyrimidine, thiophene, and pyrrole
fragments were synthesized, and their electrochemical properties were studied.
DOI: 10.1134/S1070427210080239
Conjugated polymers exhibiting semiconductor
properties acquired very high importance recently as
active materials for optical devices such as polymeric
light-emitting diodes (PLEDs), displays, photovoltaic
cells, and lasers, and also for field transistors and sensors
[1–13].
containing electron-excessive thiophene and electron-
deficient pyrimidine rings. By their electrochemical
polymerization, we prepared polymer films on the
surface of an indium–tin oxide (ITO) working electrode
[16]. Compounds in which pyrimidine fragments are in
a common conjugation chain with other heterocycles
and with aromatic rings have also been synthesized [17,
18].
A particular place among conjugated polymers is
occupied by polymers that contain in the conjugation
chain electron-deficient and electron-excessive
The goal of this study is preparation of polymeric
materials using chalcone derivatives containing
pyrimidine, thiophene, and pyrrole fragments.
heterocycles
simultaneously.
Introduction
of
a pyrimidine ring into the center of a banana-shaped
molecule strongly alters the physical properties of the
molecule such as mesomorphism, fluorescence, and
solvatochromism [14]. π-Deficient heterocycles can
be readily reduced, and polymers prepared from such
comonomers are readily n-doped. Introduction into the
pyrimidinestructureofexternalπ-excessiveheterocycles
allows preparation of polymers and oligomers that can
be both n- and р-doped. Such compounds are of much
interest, because, e.g., in fabrication of emitting devices
smaller number of polymer layers in the device structure
is required, which makes the device more efficient [15].
The use of p-aminoacetophenone as methylene
component in preparation of chalcones allowed the
range of new conjugated monomers to be considerably
expanded. The starting chalcone, (4-aminophenyl)-
3-(thiophen-2-yl)prop-2-en-1-one (1), was prepar-ed
by heating of thiophenecarbaldehyde with p-amino-
acetophenone in the presence of an aqueous alkali
solution (Scheme 1).
The reaction of 1 with 2,5-dimethoxytetrahydrofuran
yielded pyrrole 2. Its reaction with guanidine sulfate,
followed by addition of hydrogen peroxide [19],
yielded pyrimidine 3 containing in the conjugation
chain electron-excessive substituents: thiophen-2-yl in
position 4 and p-(1Н-pyrrol-1-yl)phenyl in position 6 of
the pyrimidine ring. To prepare pyrimidine 5 containing
In π-conjugated materials, pyrimidines can be used
as electron-deficient fragments in the center of the
molecule, with electron-donor fragments linked to
them. Previously we prepared novel promising materials
of the structure D–A–D (donor–acceptor–donor),
1444

NEW CONJUGATED MONOMERS AND OLIGOMERS DERIVED FROM CHALCONES
1445
Scheme 1.
NH2
N
a
a
N
b
S
N
N
S
S
1
O
N
O
3
2
NH2
1
3
2
c
d
d
N
5
NH2
S
S
N
N
N
4
N
NH2
5
4
Here a, d is treatment with 2,5-dimethoxytetrahydrofuran and acetic acid; b, c is treatment with guanidine sulfate and H2O2.
two pyrrole rings, we also used chalcone 1, from which
we initially prepared 2-amino-4-(aminophenyl)-6-
(thiophen-2-yl)pyrimidine 4. The reaction of 4 with
2,5-dimethoxytetrahydrofuran yielded 2-(1H-pyrrol-
1-yl)-4-[4-(1H-pyrrol-1-yl)phenyl]-6-(thiophen-2-yl)
pyrimidine (5) (Scheme 1).
(11), whose condensation with 2-pyrrolecarbaldehyde
in an alcoholic alkaline medium yielded chalcone 12
(Scheme 2).
The use of p-aminoacetophenone in the Paal–
Knorr reaction also allows preparation of conjugated
monomers, oligomers, and polymers containing
various heterocycles in the conjugation chain. Starting
Oligomers and polymers containing a 3,4-ethylene-
dioxythiophene fragment, which has a lower oxidation
potential than thiophene and readily undergoes
electrochemical polymerization, play an important
role in the development of diverse electronic devices.
Therefore, it was interesting to replace in chalcone
1 the thiophene ring by the ethylenedioxythiophene
ring. With 3,4-ethylenedioxythiophenecarbaldehyde
taken instead of thiophenecarbaldehyde, following
Scheme 1, we prepared 1-(4-aminophenyl)-3-(3,4-
ethylenedioxythiophen-2-yl)prop-2-en-1-one (6) and
1-[4-(pyrrol-1-yl)phenyl]-3-(3,4-ethylenedioxythio-
phen-2-yl)prop-2-en-1-one (7). From these com-
pounds, in turn, we synthesized 2-amino-4-(4-
aminophenyl)-6-(3,4-ethylenedioxythiophen-2-yl)
pyrimidine (8) and 2-(pyrrol-1-yl)-4-[4-(pyrrol-1-yl)
phenyl]-6-(3,4-ethylenedioxythiophen-2-yl)pyrimidine
(9). Replacement of thiophenecarbaldehyde by
2-pyrrolecarbaldehyde led to the synthesis of chalcone
10, 1-(4-aminophenyl)-3-(1H-pyrrol-2-yl)prop-2-en-
1-one. By the reaction of p-aminoacetophenone with
2,5-dimethoxytetrahydrofuran in refluxing acetic
acid, we prepared 1-acetyl-4-(pyrrol-1-yl)benzene
from
1,4-di(thiophen-2-yl)butane-1,4-dione
and
p-aminoacetophenone, we synthesized a substituted
acetophenone, 1-(4-acetylphenyl)-2,5-di(thiophen-2-
yl)-1Н-pyrrole 13. By its condensation in an alcoholic
alkaline medium, we prepared chalcones containing
thiophene (14) and 3,4-ethylenedioxythiophene (15)
fragments. For chalcone 15, this synthesis failed.
Therefore, it was synthesized by the Paal–Knorr reaction
from 1,4-di(2-thienyl)butane-1,4-dione and chalcone
6 in xylene in the presence of p-toluenesulfonic acid
(TsOH) (Scheme 3).
Electrochemical polymerization of conjugated
monomers is one of the main procedures for direct
preparation of polymer films in both doped and neutral
states on electrode surfaces. Thiophenes are used as
terminal groups of the monomer most frequently;
pyrroles are also used for this purpose. For example,
polymers containing pyridine and bipyridine electron-
deficient fragments in the center of the monomer were
prepared by this procedure. Generally, polymers with
electron-deficient heterocycles located in the center of
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 83 No. 8 2010

1446
BUSHUEVA et al.
Scheme 2.
O
O
NH2
NH2
O
N
S
S
S
N
N
O
6
8
O
7
6
NH2
7
NH2
O
8
N
N
N
S
O
H
N
N
10
N
10
N
9
O
N
12
H
O
CH3
12
9
11
11
Scheme 3.
O
S
N
S
S
N
S
O
S
S
O
S
CH3
O
N
S
15
O
14
13
13
14
15
1
the monomer are less stable in the p-doped state than in
the n-doped state [20, 21]. The electrochemical behavior
of chalcones was studied previously in [22–24]. It was
shown that chalcones undergo irreversible oxidation
in the anodic region and reduction and dimerization
in the cathodic region. The possibility of preparing
polymer films based on chalcones containing carbazole
fragments was demonstrated, and their electrochromic
properties and redox stability was examined.
(Aldrich). The Н NMR spectra were recorded on
a Mercury plus 300 spectrometer, with HMDS as internal
reference. Electrochemical studies were performed on
an IPC-compact device with an EM-04 electrochemical
sensor. Mass-spectrometric analysis was performed
with an Agilent Technologies 6890N/5975B gas
chromatograph–mass spectrometer (HP-5ms column,
30 × 0.25 mm, 0.25 μm, carrier gas He, ionization by
electron impact, 70 eV). The UV spectra were recorded
with an SF 2000 spectrophotometer (OKB Spektr). The
reaction progress and the product purity were monitored
by TLC on Silufol UV-254 plates.
EXPERIMENTAL
We used the following materials: thiophene,
4-aminoacetophenone, 2,5-dimethoxytetrahydrofuran
(Alfa Aesar), silica gel (Lancaster), and pyrrole
1-R1-3-R2-Prop-2-en-1-ones (chalcones) 1, 2, 6,
7, and 10 (general procedure). A flask equipped with
a stirrer was charged with 150 ml of a 2% NaOH
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 83 No. 8 2010

NEW CONJUGATED MONOMERS AND OLIGOMERS DERIVED FROM CHALCONES
1447
solution, 0.03 mol of appropriate ketone, and 0.03 mol of
appropriate aldehyde. The mixture was refluxed for 2 h.
The precipitate formed after cooling was filtered off and
washed on the filter with a double excess of cold water.
Thechalconesobtainedwerepurifiedbyrecrystallization
from ethanol or by column chromatography on silica gel
(eluent CH2Cl2).
spectrum (CDСl3, δ, ppm, J, Hz): 4.25 m (2Н, ОСН2),
4.34 m (2Н, ОСН2), 6.39 t (2Н, pyrrole, J 1.95), 6.50 s
(1H, Th), 7.17 t (2Н, pyrrole, J 2.1), 7.31–7.36 d (1Н,
СН=СН–СО, J 15.3), 7.48 d (2Н, Ph, J 8.7), 7.84–
7.89 d (1Н, СН=СН–СО, J 15.0), 8.08 d (2Н, Ph, J 8.4).
IR spectrum, ν, cm–1: 1650 (C=O), 1610 (C=C), 1585
(C=C), 1560 (C=C). UV spectrum (CH2Cl2), λmax 245.0,
370.8 nm.
1-(4-Aminophenyl)-3-(thiophen-2-yl)prop-2-en-
1-one (1). Yield 64%, mp 94–96°С. 1H NMR spectrum
(CDСl3, δ, ppm, J, Hz): 4.14 br.s (2Н, NH2), 6.68 d (2Н,
Ph, J 8.7), 7.06 t (1Н, СН-Th, J 3.6), 7.31–7.38 m (2Н,
SCCH-Th, СО–СН=СН), 7.87–7.93 m ( 4Н, SCH-Th,
Ph, СО–СН=СН). IR spectrum, ν, cm–1: 3450 (NH2),
1625 (C=O), 1596 (C=C), 1557 (C=C).
1-(4-Aminophenyl)-3-(1Н-pyrrol-2-yl)prop-2-
1
en-1-one (10). H NMR spectrum (CDСl3, δ, ppm, J,
Hz): 4.10 br.s (2H, NH2), 6.33 m (1H, pyrrole), 6.63 m
(1Н, pyrrole), 6.94 m (2Н, pyrrole), 7.15 d (1Н, СОСН,
J 15.3), 7.70 d (1Н, СН, J 15.3), 7.80 dd (2Н, phenyl,
J 8.7), 7.92 dd (2Н, phenyl, J 8.7), 8.82 (1H, NH).
1-(4-Aminophenyl)-3-(3, 4-ethylenedi-
1-(4-Acetylphenyl)-2,5-di(2-thienyl)-1Н-
pyrrole (13). To a suspension of 1.25 g (0.005 mol)
of 1,4-di(thiophen-2-yl)-1,4-butanedione and 0.95 g
(0.007 mol) of p-aminoacetophenone in 85 ml of
absolute toluene, we added 0.11 g (0.00058 mol) of
p-toluenesulfonic acid monohydrate. The mixture was
refluxed for 24 h (the reaction progress was monitored
by TLC), cooled, and washed with water. The organic
layer was dried over Na2SO4, the solvent was distilled
off, and the dark solid residue was chromatographed on
silica gel (eluent CH2Cl2). Yield 5%, mp 176–177°С.
1H NMR spectrum (CDСl3, δ, ppm, J, Hz): 2.63 s (3Н,
СОСН3), 6.50 d (2Н, thiophene, J 3.6), 7.07–7.09 dd
(2Н, thiophene, J 5.1), 7.34–7.37 dd (2Н, phenyl,
J 9.01), 7.98 (2Н, phenyl, J 7.84).
oxythiophen-2-yl)prop-2-en-1-one (6). Yield 84%,
1
mp 222–225°С. H NMR spectrum (CDСl3, δ, ppm,
J, Hz): 4.10 s (2H, NH2), 4.23 m (2Н, ОСН2), 4.32 m
(2Н, ОСН2), 6.43 s (1Н, Th), 6.68 d (2Н, Ph, J 8.7),
7.29–7.34 d (1Н, СН=СН–СО, J 15.3), 7.78–7.83 d
(1Н, СН=СН–СО, J 15.0), 7.88 d (2Н, Ph, J 8.7). IR
spectrum, ν, cm–1: 3447 (NH2), 1639 (С=О), 1595
(С=С), 1570 (C=C).
1-[4-(Pyrrol-1-yl)phenyl]-3-(thiophen-2-yl)prop-
2-en-1-one (2) was prepared by refluxing for 1 h 1.15 g
(0.005 mol) of chalcone 1 and 0.66 g (0.005 mol) of
2,5-dimethoxyTHF in a minimal amount of glacial
СН3СООН. After that, the reaction mixture was
cooled and poured into ice-cold water. The precipitate
that formed was filtered off, dried in air, and purified
by recrystallization from ethanol or by column
chromatography (silica gel, eluent СН2Сl2). Yield 62%,
1-{4-[2,5-Di(2-thienyl)pyrrol-1-yl]phenyl}-3-(2-
thienyl)prop-2-en-1-one (14) was prepared similarly to
13 and purified by column chromatography (silica gel,
1
1
mp 140–141°С. H NMR spectrum (CDСl3, δ, ppm, J,
eluent CH2Cl2). Yield 3%, mp 226–228°С. H NMR
Hz): 6.39 t (2Н, pyrrole, J 2.25), 7.09 t (1Н, CH-Th,
J 3.6), 7.17 t (2Н, pyrrole, J 2.25), 7.31–7.37 m (2Н,
SCCH-Th, CH=CH–CO), 7.43 d (1Н, SCH-Th, J 5.1),
7.49 d (2Н, Ph, J 8.7), 7.94–7.99 d (1Н, CH=CH–CO,
J 15.3), 8.08 d (2Н, Ph, J 8.7). Mass spectrum, m/z (I,
%): 279.00 [M+] (100.0), (С17Н13NOS, Мcalc 279.36).
IR spectrum, ν, cm–1: 1650 (С=О), 1600 (С=С), 1570
(С=С). UV spectrum (CH2Cl2), λmax 246.0, 350.9 nm.
spectrum (CDСl3, δ, ppm, J, Hz): 6.51 d (3Н, 3SCCH-
Th, J 3.75), 6.54 s (2H, 2CH-pyrrole), 6.81 t (3Н, 3CH-
Th, J 3.6), 7.08 d (3Н, 3SCH-Th, J 5.1), 7.32–7.37 d
(1Н, СО-СН=СН, J 15.0), 7.39 d (2Н, Ph, J 8.4), 7.96–
8.01 d (1Н, СО–СН=СН, J 15.3), 8.03 d (2Н, Ph, J 9.0).
IR spectrum, ν, cm–1: 1719 (С=О), 1578 (С=С). UV
spectrum (CH2Cl2), λmax 270.9, 339.9 nm.
1-{4-[2,5-Di(2-thienyl)pyrrol-1-yl]phenyl}-3-(3,4-
3-(3,4-Ethylenedioxythiophen-2-yl)-1-[4-(pyrrol-
1-yl)phenyl]prop-2-en-1-one (7) was prepared from
1.44 g (0.005 mol) of 1-(4-aminophenyl)-3-(3,4-
ethylenedioxythiophen-2-yl)prop-2-en-1-one (6) by
the procedure similar to preparation of chalcone 2.
The product was chromatographed on silica gel
ethylenedioxythiophen-2-yl)prop-2-en-1-one
(15).
Asuspension of 0.13 g (37 mmol) of 1-(4-acetylphenyl)-
2,5-di(2-thienyl)-1Н-pyrrole (13) and 0.06 g (37 mmol)
of 3,4-ethylenedioxythiophene-2-carbaldehyde in
20 ml of methanol was heated until the reactants
fully dissolved. Then the mixture was cooled to room
temperature, and a solution of 0.56 g of KOH in 10 ml of
1
(eluent СН2Сl2). Yield 78%, mp 236–238°С. H NMR
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 83 No. 8 2010

1448
BUSHUEVA et al.
1
methanol was added. The mixture was refluxed for 5 h,
and the precipitate that formed was filtered off, dried
in air, and chromatographed on a column (silica gel,
pyrimidine (4). Yield 34%, mp 221–223°С. H NMR
spectrum (CDСl3, δ, ppm, J, Hz): 5.05 br.s (4Н, 2NH2),
6.75 d (2Н, Ph, J 8.7), 7.13 t (1Н, CH-Th, J 4.5), 7.28 s
(1Н, pyrimidine), 7.45 d (1Н, SCCH-Th, J 5.1), 7.74 d
(1Н, SCH-Th, J 3.6), 7.90 d (2Н, Ph, J 8.4). Mass
spectrum, m/z (I, %): 268.05 [M+] (100.0), (С14Н12N4S,
Мcalc 268.34). UV spectrum (CH2Cl2), λmax 235.0,
291.9, 343.9, 354.9 nm.
1
eluent CH2Cl2). Yield 37%, mp 197–199°С. Н NMR
spectrum (CDСl3, δ, ppm, J, Hz): 4.25 m (2Н, ОСН2),
4.35 m (2Н, ОСН2), 6.48 d (2Н, 2SCCH-Th), 6.51 s
(1Н, SCH-Th), 6.54 s (2Н, 2CH-pyrrole), 6.81 t (2Н,
2СН-Th, J 3.6), 7.07 d (2Н, 2SCH-Th, J 5.1), 7.33–
7.38 d (1Н, CO–CH=CH, J 15.0), 7.37 d (2Н, Ph, J 8.7),
7.85–7.90 d (1Н, CO–CH=CH, J 15.6), 8.03 d (2Н, Ph,
J 9.0).
2-(Pyrrol-1-yl)-4-[4-(pyrrol-1-yl)phenyl]-6-(2-
thienyl)pyrimidine (5). Yield 19%, mp 155–157°С.
1H NMR spectrum (CDСl3, δ, ppm, J, Hz): 6.37 t (2Н,
pyrrole, J 2.25), 6.40 t (2Н, pyrrole, J 2.1), 7.18–7.21 m
(2Н, SCCH-Th, CH-Th), 7.53 d (2Н, Ph, J 8.7), 7.56 t
(2Н, pyrrole, J 2.4), 7.69 s (1Н, pyrimidine), 7.89 d
(1Н, SCH-Th, J 3.6), 7.95 t (2Н, pyrrole, J 2.4), 8.25 d
(2Н, Ph, J 8.4). Mass spectrum, m/z (I, %): 368.05
[M+] (100.0), (С22Н16N4S, Мcalc 368.46). UV spectrum
(CH2Cl2), λmax 256.0, 302.9, 336.9, 357.9 nm.
1-[4-(Pyrrol-1-yl)phenyl]-3-(pyrrol-2-yl)prop-
2-en-1-one (12) was prepared similarly to 15 from
4-(pyrrol-1-yl)acetophenone (0.12 g, 0.00065 mol)
and pyrrole-2-carbaldehyde (0.06 g, 0.00065 mol).
The product was chromatographed on silica gel (eluent
acetone : hexane = 1 : 3). Yield 12%, mp 207–208°С.
1Н NMR spectrum (CDСl3, δ, ppm, J, Hz): 6.34 m (1Н,
HNCCH-pyrrole), 6.39 t (2Н, pyrrole, J 2.25), 6.73 m
(1Н, СН-pyrrole), 7.00 m (1Н, HNCH-pyrrole), 7.10–
7.15 d (1Н, СН=СН–СО, J 15.3), 7.18 t (2Н, pyrrole,
J 2.25), 7.48 d (2Н, Ph, J 9.0), 7.71–7.76 d (1Н, СН=СН–
СО, J 15.3), 8.06 d (2Н, Ph, J 9.0), 8.82 s (1Н, NH).
UV spectrum (CH2Cl2), λmax 321.9, 374.8 nm. Mass
spectrum, m/z (I, %): 262.1 [M+] (100.0), (С17Н14N2OS,
Мcalc 262.3).
2-Amino-4-(4-aminophenyl)-6-(3,4-ethylene-
dioxythiophen-2-yl)pyrimidine (8). Yield 13%,
mp 227–230°С. H NMR spectrum (CDСl3, δ, ppm, J,
Hz): 4.28 m (2Н, OCH2), 4.41 m (2Н, OCH2), 5.01 s
(4H, 2NH2), 6.05 s (1H, Th), 6.50 s (1H, pyrimidine),
6.61 d (2Н, Ph, J 9.0), 6.73 d (2Н, Ph, J 8.7). UV
spectrum (CH2Cl2), λmax 246.0, 283.9, 349.9 nm.
1
2-(Pyrrol-1-yl)-4-[4-(pyrrol-1-yl)phenyl]-6-(3,4-
2-Amino-4-R1-6-R2-pyrimidines3–5and8(general
procedure). A mixture of 0.025 mol of appropriate 1-R1-
3-R2-prop-2-en-1-one, 4.10 g (0.019 mol) of guanidine
sulfate, and 23 ml of 50% aqueous KOH solution in
60 ml of ethanol was refluxed with stirring for 1 h, after
which 9 ml of a 33% Н2О2 solution was added dropwise
under the same conditions over a period of 1 h. The
hot reaction mixture was poured into ice-cold water,
and the precipitate that formed was filtered off, dried,
and chromatographed on silica gel (eluent СН2Сl2 or
acetone : hexane = 1 : 2).
ethylenedioxythiophen-2-yl)pyrimidine (9). Yield
18%, mp 46–48°С. H NMR spectrum (CDСl3, δ,
1
ppm, J, Hz): 4.30 m (2Н, OCH2), 4.46 m (2Н, OCH2),
6.35 t (2Н, pyrrole, J 2.4), 6.40 t (2Н, pyrrole, J 2.25),
6.60 s (1Н, Th), 7.18 t (2Н, pyrrole, J 2.1), 7.53 d
(2Н, Ph, J 8.7), 7.93 t (2Н, pyrrole, J 2.4), 8.01 s (1Н,
pyrimidine), 8.25 d (2Н, Ph, J 8.7). UV spectrum
(CH2Cl2), λmax 259.9, 302.9, 353.9, 368.2 nm.
4-(Pyrrol-1-yl)acetophenone (11). A mixture of
0.68 g (0.005 mol) of 4-aminoacetophenone and 0.66 g
(0.005 mol) of 2,5-dimethoxytetrahydrofuran was
refluxed in a minimal amount of glacial CH3COOH
for 1 h. After cooling, the mixture was poured into
cold water and extracted with СН2Сl2 (3 × 75 ml). The
organic layers were combined, washed with water,
saturated aqueous NaHCO3 solution, and again water
and dried over Na2SO4. The solvent was evaporated,
and the dark residue was chromatographed on silica gel
2-Amino-4-[4-(pyrrol-1-yl)phenyl]-6-(2-thienyl)
1
pyrimidine (3). Yield 34%, mp 221–223°С. H NMR
spectrum (CDСl3, δ, ppm, J, Hz): 5.14 br.s (2Н, NH2),
6.38 t (2Н, pyrrole, J 2.25), 7.14 t (1Н, СН-Th, J 3.9),
7.16 t (2Н, pyrrole, J 2.1), 7.36 s (1Н, pyrimidine),
7.48 d (1Н, SCCH-Th, J 5.1), 7.50 d (2Н, Ph, J 8.7),
7.78 d (1Н, SCH-Th, J 3.6), 8.11 d (2Н, Ph, J 9.0). Mass
spectrum, m/z (I, %): 318.10 [M+] (100.0), (С18Н14N4S,
Мcalc 318.40). UV spectrum (CH2Cl2), λmax 246.0,
301.9, 357.9 nm.
1
(eluent СН2Сl2). Yield 50%, mp 118–120°С. H NMR
spectrum (CDСl3, δ, ppm, J, Hz): 2.61 s (3Н, СН3),
6.38 t (2Н, pyrrole, J 2.25), 7.16 t (2Н, pyrrole, J 2.1),
7.45 d (2Н, Ph, J 9.3), 8.02 d (2Н, Ph, J 9.0).
2-Amino-4-(4-aminophenyl)-6-(2-thienyl)
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 83 No. 8 2010

NEW CONJUGATED MONOMERS AND OLIGOMERS DERIVED FROM CHALCONES
1449
8. Günes, S., Neugebauer, H., and Sariciftci, N.S., Chem.
Rev., 2007, vol. 107, no. 4, pp. 1324–1338.
CONCLUSION
9. Roncali, J., Macromolecules. Rapid Commun., 2007,
Previously unknown pyrimidines and pyrroles
containing both donor and acceptor heterocycles in the
conjugation chain were synthesized. Films of a series of
conjugated polymers on the surface of a glassy carbon
electrode were prepared, and their redox stability was
studied.
vol. 28, no. 17, pp. 1761–1775.
10. Grimsdale, A.C. and Müllen, K., Macromolecules. Rapid
Commun., 2007, vol. 28, no. 17, pp. 1676–1702.
11. Chen, L.-M., Hong, Z., Li, G., and Yang, Y., Adv. Mater.,
2009, vol. 21, nos. 14–15, pp. 1431–1449.
12. Beaujuge, P.M. and Reynolds, J.R., Chem. Rev., 2010,
vol. 110, no. 1, pp. 268–320.
ACKNOWLEDGMENTS
13. Po, R., Maggini, M., and Camaioni, N., J. Phys. Chem.,
The study was financially supported by the
Russian Foundation for Basic Research (project no.
10-03-96038-r-ural-a) and Analytical Departmental
Target Program of the Federal Education Agency of
the Russian Federation “Development of the Scientific
Potential of Higher School.”
2010, vol. 114, no. 2, pp. 695–706.
14. Achelle, S., Ramondenc, Y., Dupas, G., and Plé, N.,
Tetrahedron, 2008, vol. 64, no. 12, pp. 2783–2791.
15. Dufrense, S., Hanan, G.S., and Skene, W.G., J. Phys.
Chem. B, 2007, vol. 111, no. 39, pp. 11407–11478.
16. Bushueva, A.Yu., Shklyaeva, E.V., and Abashev, G.G.,
Mendeleev Commun., 2009, vol. 19, no. 6, pp. 329–331.
REFERENCES
17. Hughes, G., Wang, Ch., Batsanov, A.S., et al., Org.
Biomol. Chem., 2003, vol. 1, no. 17, pp. 3069–3077.
1. Mittschake, U. and Bäurle, P., J. Mater. Chem., 2000,
18. Wong, T., Hung, T.S., Wu, Ch.-Ch., et al., Org. Lett.,
vol. 10, pp. 1471–1507.
2002, vol. 4, no. 4, pp. 513–516.
2. Brnius, M.T., Inbasekaran, M., O’Brien, J., and Wu, W.,
19. Varga, L., Nagy, T., Kövesdi, I., et al., Tetrahedron, 2003,
Adv. Mater., 2000, vol. 12, pp. 1737–1750.
vol. 59, no. 5, pp. 655–662.
3. Akcelerud, L., Prog. Polym. Sci., 2003, vol. 28, pp. 875–
20. Jenkins, I.H., Salzner, U., and Pickup, P.G., Chem. Mater.,
962.
1996, vol. 8, no. 10, pp. 2444–2450.
4. Shirota, Y. and Kageyama, H., Chem. Rev., 2007, vol. 107,
21. Jenkins, I.H., Rees, N.G., and Pickup, P.G., Chem. Mater.,
no. 4, pp. 953–1010.
1997, vol. 9, no. 5, pp. 1213–1216.
5. Murphy, A.R. and Frechet, J.M.J., Chem. Rev., 2007,
22. Taran, L.A., Berezina, S.I., Smolentseva, L.G., and
Kitaev, Yu.P., Izv. Akad. Nauk SSSR, Ser. Khim., 1974,
pp. 2611–2613.
vol. 107, no. 4, pp. 1066–1096.
6. Samuel, I.D.W. and Turnbull, G.A., Chem. Rev., 2007,
vol. 107, no. 4, pp. 1272–1295.
23. Brovelly, F., Rivas, B.L., and Bazaez, L., J. Chil. Chem.
Soc., 2003, vol. 48, no. 4, pp. 135–140.
7. Thomas, S.W., Joly, G.D., and Swager, T.M., Chem. Rev.,
2007, vol. 107, no. 4, pp. 1339–1386.
24. Syutkin, R.V., Cand. Sci. Dissertation, Perm, 2009.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 83 No. 8 2010