Synthesis and characterization of poly{2-[3-(1H-pyrrol-2-yl)phenyl]-1H- pyrrole} and its copolymer with EDOT1

Article abstract of DOI:10.1134/S1070363211120164

A pyrrole-functionalized monomer 2-[3-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole (PyPhPy) was synthesized. The structure of monomer was investigated by Nuclear Magnetic Resonance (¹H NMR) and Fourier Transform Infrared (FTIR) spectroscopy. The chemical

Full text of DOI:10.1134/S1070363211120164

ISSN 1070-3632, Russian Journal of General Chemistry, 2011, Vol. 81, No. 12, pp. 2510–2516. © Pleiades Publishing, Ltd., 2011.
Synthesis and Characterization
of Poly{2-[3-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole}
and Its Copolymer with EDOT1
Ersen Turaça, Metin Akb, Ertuğrul Şahmetlioglua,
M. Kasım Şenerc, and Mehmet Arif Kayac
a Department of Chemistry, Nigde University, 51100, Nigde, Turkey
e-mail: sahmetlioglu@nigde.edu.tr
b Department of Chemistry, Pamukkale University, 20017, Denizli, Turkey
e-mail: metinak@pau.edu.tr
c Department of Chemistry, Yıldız Technical University, 34210 Davutpaşa, Istanbul, Turkey
e-mail: mkasimsener@gmail.com
Received July 29, 2010
Abstract—A pyrrole-functionalized monomer 2-[3-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole (PyPhPy) was
synthesized. The structure of monomer was investigated by Nuclear Magnetic Resonance (1H NMR) and
Fourier Transform Infrared (FTIR) spectroscopy. The chemical polymerization of PyPhPy (CPyPhPy) was
realized using FeCl3 as the oxidant. The electrochemical oxidative polymerization of polymer P(PyPhPy) and
its copolymer with 3,4-ethylenedioxythiophene poly(2-[3-(1H-pyrrol-2-yl)phenyl]-1H-pyrrole-co-3,4-
ethylenedioxythiophene) [P(PyPhPy-co-EDOT)] were achieved via potentiodynamic method by using NaClO4/
LiClO4 as the supporting electrolyte in CH3CN. Characterizations of the resulting polymers were performed by
cyclic voltammetry (CV), FTIR, scanning electron microscopy (SEM), UV–Visible spectrophotometry (UV–
Vis) and thermogravimetry analyses (TGA). Electrical conductivity of CPyPhPy, P(PyPhPy), and P(PyPhPy-
co-EDOT) were measured by four-probe technique.
DOI: 10.1134/S1070363211120164
INTRODUCTION
conductivity and environmental stability. It has been
considered for use in many applications, including
high energy batteries, electrochromic devices, and
modified electrodes [19]. A number of procedures
have been proposed to prepare polypyrrole composites
to improve the mechanical properties of polypyrrole.
PPy as a conductive polymer was electrochemically
synthesized for the first time by Weiss et al. in 1965
[20] and later was extensively studied by Diaz [21].
Conductive and free-standing films were obtained by
potentiostatic anodic polymerization of pyrrole. Many
research efforts also have been dedicated to obtaining
stable, processable, and conductive polymeric
materials. Several composites of conducting polymers
have been prepared for the simple reason of having
polymers with good thermal and physical charac-
teristics. In some cases, grafting between the insulating
and the conducting polymers has also been observed to
a certain extent [22–24].
The search for organic conducting polymers has
started in 1970s and up to date is largely focused on
polyfuran [1], polythiophene [2–5], polypyrrole, and
their derivatives [6]. The ability to dope conjugated
polymers electrochemically is significant due to the
easy combination of synthesis and characterization
methods. Many applications of conjugated polymers,
such as light emitting electrochemical cells [7, 8],
microactuators [9, 10], energy storage [11], photo-
voltaic [12] and electrochromic devices (ECDs) [13–
17], and sensors [18] are based on electrochemical
transition between doped and neutral states or rely on
the stability of a specific doping level.
Polypyrrole (PPy) is one of the well-known
conjugated heterocyclic polymers having high
1
The article was submitted by the authors in English.
2510

SYNTHESIS AND CHARACTERIZATION OF POLY{2-[3-(1H-PYRROL-2-YL)PHENYL]-...
2511
Electrochemical
polymerization
N
H
N
n
NH
HN
H
Fig. 1. Synthesis of P(PyPhPy).
O
O
+
NH
HN
S
O
Electrochemical
polymerization
O
O
O
z
x
N
N
H
y
S
S
H
Fig. 2. Synthesis of copolymers of PyPhPy with EDOT.
In 1991, Jonas et al. [25] synthesized 3,4-ethylene-
dioxythiophene (EDOT) by locking the 3- and 4-posi-
tions of thiophene with an ethylenedioxy group
yielding a highly electron-rich fused heterocycle which
had low oxidation potential and was free from the
possible α, β and β, β linkages. Poly(3,4-ethylenedi-
oxythiophene) (PEDOT) exhibits an optical band gap
of 1.6 eV. Doped PEDOT is almost transparent in the
visible region, and the neutral polymer is dark blue.
Thus, this material is significant for its cathodically
coloring electrochromic properties in device applica-
tions [26].
EXPERIMENTAL
Nitromethane (Aldrich), iron(III)chloride (Fluka),
methanol (Merck), NaOH (Merck), phosgene (20%
solution in toluene) (Aldrich), N,N-dimethylform-
amide (DMF) (Aldrich), tetrahydrofuran (THF)
(Aldrich),
3,4-ethylenedioxythiophene
(EDOT)
(Aldrich), potassium tert-butoxide (Merck), sodium
sulfate (Na2SO4) (Merck), chloroform (Aldrich), silica
gel (Merck), dichloromethane (DCM) (Merck), hexane
(Merck) were used as received. The electrolysis
solvent, acetonitrile (CH3CN) (Merck) was used
without further purification. The supporting
electrolytes, tetrafluoroammonium tetrahexafluoro-
borate (Merck), sodium perchlorate (NaClO4)
(Aldrich), and lithium perchlorate (LiClO4) (Aldrich)
were used as received.
In the present work, 2-[3-(1H-pyrrol-2-yl)phenyl]-
1H-pyrrole was for the first time synthesized as a
1
monomer. H-NMR and FT–IR were used to analyze
the structure of pyrrole derivative. The polymer
(CPyPhPy) synthesized via chemical oxidative method
was characterized by FT–IR. The electrochemical
oxidative polymerization [P(PyPhPy)] of the monomer
and its copolymer with 3,4-ethylenedioxythiophene
[P(PyPhPy-co-EDOT)] were performed via potentio-
dynamic method by using NaClO4/LiClO4 as the
supporting electrolyte in CH3CN. Characterizations of
the resulting polymers were performed by CV, FT–IR,
SEM, UV–Vis, and TGA. Electrical conductivity of
CPyPhPy, P(PyPhPy), P(PyPhPy-co-EDOT), and
PEDOT were measured by the four-probe technique.
1
The monomer was characterized using H NMR
spectra (Bruker-Instrument-NMR Spectrometer DPX-
400) recorded at 25°C using deuterated CDCl3 as
solvent. The FTIR spectra were recorded on JASCO
FT/IR-300E spectrometer. The FTIR spectra were
recorded using KBr pellets in the range 4000–400 cm–1.
UV-visible spectra were taken using DCM as the
solvent on a Shimadzu MultiSpec-1501 instrument.
Cyclic voltammograms were recorded in NaClO4
(0.1 M) and LiClO4 (0.1 M)/CH3CN electrolyte-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 12 2011

2512
TURAÇ et al.
solvent couple with a system consisting of a poten-
Hd
He
Hc
tiostat (CH Instruments 600) and a CV cell containing
Pt-flake working electrode, Pt counter electrode, and a
Ag wire pseudo reference electrode. Measurements
were carried out at room temperature. Thermo-
gravimetric analyses were performed between 25 and
1100°C under nitrogen at a heating rate of 5°C min–1
using Perkin–Elmer Pyrisdiamond 6.0 model TG/
DTA. The particle morphology of the polymer films
was examined by means of scanning electron
microscopy (Leo 440) operated at 20 kV. Electrical
conductivity of the polymer was measured at room
temperature by using four probe technique with a
custom made instrument.
Hc
Hb
Hf
Hc
N
Hc
N
Hb
Hf
Hf
He
He
Ha
Hd
Ha
Hd
Ha
9
8
7
6
5
4
3
2
1
0
δ, ppm
Synthesis of 2-[3-(1H-pyrrol-2-yl)phenyl]-1H-
pyrrole (PyPhPy). 2-[3-(1H-pyrrol-2-yl)phenyl]-1H-
pyrrole was prepared according to the published
procedure [27]. A mixture of N,N'-diallylisophthal-
diamide (2.44 g, 10 mmol), phosgene (20% solution in
toluene, 40 ml), and DMF (4 drops) were stirred under
argon atmosphere for 15 h at room temperature. The
resulting mixture was then heated to 40–45°C for 2 h,
after which the solvent was removed in vacuo (caution:
phosgene is highly toxic and must be handled with
care). The residue was dissolved in THF (60 ml) and
added dropwise with stirring to a solution of potassium
tert-butoxide (5.89 g, 52 mmol) in THF (60 ml) at 5–
10°C under argon. After stirring for 1 h at this
temperature, the reaction mixture was poured into ice
water and extracted with chloroform (3×100 ml). The
organic phase was dried (Na2SO4) and evaporated to
dryness. The residue was subjected to column
chromatography (silicagel, dichloromethane eluent) to
give crude product, which upon recrystallization from
dichloromethane/hexane afforded PyPhPy in the form
of a white solid. This compound was soluble in
acetone, chloroform, THF, DMSO, acetonitrile, and
Fig. 3. 1H NMR spectrum of PyPhPy.
CPyPhPy
P(PyPhPy)
PyPhPy
4000 3500 3000 2500 2000 1500 1000
ν, cm–1
Fig. 4. FT–IR spectrum of PyPhPy, P(PyPhPy) and
CPyPhPy.
1
dichloromethane (mp 163°C); H NMR (CDCl3), δ:
6.21 d (J = 2.8 Hz, 2H; Hf), 6.48 t (2H; He), 6.80 d
(2H; Hd), 7.30– 7.39 m (3H; Hc), 7.52 t (J = 1.6 Hz,
1H; Hb), 8.40 s (2H; Ha); UV–Vis λmax (nm) in
dichloromethane: 585, 407.
Synthesis
of
polymer
by
chemical
polymerization. PyPhPy (1×10–3 M) was dissolved in
nitromethane (15 ml). Iron (III) chloride (2×10–3 M)
was dissolved in 15 ml of nitromethane and placed in a
three-neck flask. Monomer solution was added drop-
wise to the iron (III) chloride solution at 0°C. The
reaction was carried out for 5 min with constant stir-
ring. The dark black product was first washed with
4000
3000
2000
1000 400
ν, cm–1
Fig. 5. FT–IR spectrum of P(PyPhPy-co-EDOT).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 12 2011

SYNTHESIS AND CHARACTERIZATION OF POLY{2-[3-(1H-PYRROL-2-YL)PHENYL]-...
2513
4.0
1.2
0.6
(b)
(a)
0.0
–4.0
0.0
–0.6
–1.2
–1.8
–2.4
–8.0
–12.0
–1.6 –1.2 –0.8 –0.4 0.0. 0.4 0.8 1.2 1.6
Potential, V
–1.6 –1.2 –0.8 –0.4 0.0. 0.4 0.8 1.2 1.6
Potential, V
3.0
2.0
(c)
1.0
0.0
–1.0
–2.0
–3.0
–4.0
–5.0
–1.6 –1.2 –0.8 –0.4 0.0. 0.4 0.8 1.2 1.6
Potential, V
Fig. 6. Cyclic voltammograms of (a) PyPhPy, (b) PyPhPy in the presence of EDOT, and (c) EDOT, on a Pt-flake working electrode
in 0.1 M LiClO4/NaClO4/CH3CN at 500 mV s–1 scan rate.
methanol, filtered and then neutralized with 30%
NaOH. This compound was insoluble in organic
solvents.
assembly was used where the working electrode was a
Pt-flake, the counter electrode was a platinum wire,
and the Ag wire electrode was used as the pseudo
reference.
Electrochemical polymerization of PyPhPy. Pre-
parative electrochemical polymerization was per-
formed by sweeping the potential between –1.5 V and
+1.5 V with 500 mV s–1 scan rate. 50 mg PyPhPy were
dissolved in CH3CN and NaClO4 (0.1 M) and LiClO4
(0.1 M) were used as the supporting electrolyte
(Fig. 1). Electrolyses were carried out using Pt
working and counter electrodes and an Ag wire
reference electrode at room temperature for 1 h. The
free standing films were washed with CH3CN several
times to remove unreacted monomer and the electrolyte.
In a previous research Nakazaki et al. [28] have
synthesized the 2-[3-(1H-pyrrol-2-yl)phenyl]-1H-
pyrrole monomer with a different method and
achieved the oxidative chemical polymerization of the
monomer. In our study, we have synthesized the
polymer and its copolymer with 3,4-ethylene-
dioxythiophene [P(PyPhPy-co-EDOT)] by electro-
chemical polymerization route.
1H NMR spectrum of PyPhPy is given in Fig. 3, δH,
ppm, (chloroform): 6.21 d (J = 2.8 Hz, 2H; Hf), 6.48 t
(2H; He), 6.80 d (2H; Hd), 7.30– 7.39 m (3H; Hc),
7.52 t (J = 1.6 Hz, 1H; Hb), 8.40 s (2H; Ha).
Synthesis of conducting copolymer of PyPhPy
with EDOT. For the synthesis of conducting
copolymer P(PyPhPy-co-EDOT), EDOT was used as
the comonomer (Fig. 2). PyPhPy (1.3×10–3 M) was
dissolved in 0.1 M NaClO4/LiClO4 in CH3CN and
1.3×10–3 M of EDOT was introduced into a single
compartment electrolysis cell. A three-electrode cell
FT–IR spectrum of the PyPhPy shows the follow-
ing absorption peaks: 3410 cm−1 (N–H), 3107 cm−1
(C–Hα stretching of pyrrole), 2973 cm−1 (aromatic C–H),
1599–1406 cm−1 (aromatic C=C stretching due to
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 12 2011

2514
TURAÇ et al.
(a)
(b)
(c)
Fig. 7. SEM micrograph of (a) P(PyPhPy), (b) PEDOT, and (c) P[(PyPhPy)-co-EDOT].
(a)
(b)
1500
800
600
1
Ipa
Ipc
1000
500
2
3
r2 = 0.9979
Ipa/Ipc
400
200
4
5
0
0
r2 = 0.998
–500
–1000
–200
–400
–600
–1500
100
200
300
400
500
–2.0 –1.5 –1.0 –0.5 0.0 0.5 1.0 1.5 2.0
Potential, V
Scan rate, mV s–1
Fig. 8. (a) Cyclic voltammogram of P(PyPhPy-co-EDOT) in monomer-free at different scan rates, mV s–1: (1) 500, (2) 400, (3) 300,
(4) 200, and (5) 100. (b) Anodic and cathodic peak currents as a function of the scan rate.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 12 2011

SYNTHESIS AND CHARACTERIZATION OF POLY{2-[3-(1H-PYRROL-2-YL)PHENYL]-...
2515
pyrrole and benzene), 730 cm−1 (C–Hα out of plane
100
bending of pyrrole) (Fig. 4).
90
80
70
60
50
40
30
20
10
0
Most of the characteristic peaks of the monomer
PyPhPy remained unperturbed upon chemical
polymerization. The intensity absorption bands of the
monomer at 3107 cm−1 and 730 cm−1 arising from C–Hα
stretching vibrations of pyrrole moiety disappeared
completely. This is an evidence of the polymerization
at the 2,5 positions of pyrrole moiety of the monomer.
The broad band observed at around 1614 cm−1 proves
the presence of polyconjugation (Fig. 4).
FTIR spectra of electrochemically synthesized
P(PyPhPy) showed the characteristic peaks of the
monomer. The peaks related to C–Hα stretching vibra-
tions of pyrrole disappeared completely. The new broad
band at around 1641 cm−1 was due to polyconjugation.
The strong absorption peak at 1119 cm−1 and 632 cm−1
was attributed to the incorporation of ClO4− ions into
the polymer film during doping process (Fig. 4).
40 100 200 300 400 500 600 700 800 900 1000 1100
Temperature, °C
Fig. 9. TGA curve of P(PyPhPy).
P(PyPhPy-co-EDOT) film was prepared via
constant potential electrolysis. Its redox switching in
monomer free electrolyte revealed a single, well-
defined redox process (Fig. 8a) as shows the cyclic
voltammogram of P(PyPhPy-co-EDOT) at different
scan rates. The current responses were directly
proportional to the scan rate indicating that the
polymer film was electroactive and well adhered to the
electrode [29]. The linear scan rate dependence with
respect to current for the anodic and cathodic peaks up
to 500 mV s–1 is illustrated in Fig. 8b.
After the electrochemical copolymerization of
PyPhPy with EDOT, the disappearance of peaks at 730
and 3107 cm–1 evidence the polymerization through
2,5 positions of pyrrole ring. The shoulder observed at
1645 cm–1 is due to the conjugation and the peak at
1144 cm–1, due to C–O–C group, indicates that EDOT
is incorporated into the polymer matrix. The peaks
appeared at 1089, 1113 and 632 cm–1 show the
presence of the dopant ion, ClO4− (Fig. 5).
Cyclic voltammogram of PyPhPy in CH3CN/
LiClO4–NaClO4 solvent/electrolyte couple indicated
an oxidation peak at –0.50 V and a reduction peak at
–0.65 V. When the range between –1.5 V and +1.5 V
(Fig. 6a) was scanned, it was observed that the
electroactivity increased with increasing scan number.
Electrical conductivity of the P(PyPhPy) and
CPyPhPy materials were measured at room tempera-
ture by using four probe technique with a custom-made
instrument. Pellets of the P(PyPhPy) and CPyPhPy for
conductivity measurement were prepared in
a
hydraulic press. The conductivities of electro-
chemically and chemically prepared polymers were
measured as 1.7×10–4 S cm–1 and 4.5×10–5 S cm–1
respectively via four probe technique. The conduc-
tivity of electrochemically prepared homopolymer was
4.5×10–5 S cm–1; whereas P(PyPhPy-co-EDOT) film
was measured as 2.5×10–3 S cm–1. Introducing EDOT
into the polymer chain increased the conductivity.
To investigate the copolymer we performed CV
studies in the presence of EDOT under the same
experimental conditions. There was a drastic change in
the voltammogram, both the current increase between
consecutive cycles and the oxidation potential of the
material were different from those of PyPhPy and
EDOT (Fig. 6c), which in fact, could be interpreted as
the formation of copolymer (Fig. 6b).
TGA of P(PyPhPy) was measured under nitrogen
atmosphere in the temperature range 25–1100°C in
order to investigate the thermal stability. The 5%
weight loss of the polymer was revealed at 110°C,
50% weight loss at 320°C, and according to the TGA
result, the carbonaceous residue values of P(PyPhPy)
was 10% at 1020°C (Fig. 9).
SEM micrographs of P(PyPhPy) (Fig. 7a) imply
that the synthesized monomer is good for film
forming. SEM micrograph of P(PyPhPy-co-EDOT)
(Fig. 7c) was different from both P(PyPhPy) and
PEDOT (Fig. 7b). This difference could be attributed
to copolymerization.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 12 2011

2516
TURAÇ et al.
10. Jager, E.W.H., Inganäs, O., and Lundström, I., Science,
CONCLUSIONS
2000, vol. 288, pp. 2335–2338.
11. Gofer, Y., Killian, J.G., Sarker, H., Poehler, T.O., and
Searson, P.C., J. Electroanal. Chem., 1998, vol. 443,
pp. 103–115.
P(PyPhPy) and CPyPhPy were synthesized by both
chemical and electrochemical oxidative polymeriza-
tions. The homopolymer of PyPhPy was also
synthesized potentiodynamically in CH3CN/NaClO4/
LiClO4 (0.1 M) solvent–electrolyte couple. The con-
ductivities of P(PyPhPy) and CPyPhPy were measured
as 1.7×10–4 S cm–1 and 4.5×10–5 S cm–1 respectively.
According to TGA results, the synthesized P(PyPhPy)
polymer is stable against heat. The synthesis of
copolymer from (2-[3-(1H-pyrrol-2-yl)phenyl]-1H-
pyrrole) PyPhPy and EDOT was successfully achieved
in CH3CN /NaClO4/LiClO4 (0.1 M) solvent-electrolyte
couple. Copolymer was characterized by CV, SEM
and FTIR studies. The conductivity of P(PyPhPy-co-
EDOT) was measured as 2.5×10–3 S cm–1. Scan rate
dependence of the peak currents measurements show
that the current responses were directly proportional to
the scan rate.
12. Yohannes, T. and Inganäs, O., J. Electrochem. Soc.,
1996, vol. 143, pp. 2310–2314.
13. Sahin, E., Camurlu, P., Toppare, L., Mercore, V.M.,
Cianga, I., and Yagci, Y., J. Electroanal. Chem.., 2005,
vol. 579, pp.
14. Aslan, E., Camurlu, P., and Toppare, L., J. Macromol.
Sci. A., 2005, vol. 42, no. 4, pp. 451–462.
15. Sonmez, G., Meng, H., and Wudl, F., Chem. Mater.,
2004, vol. 16, pp. 574–580.
16. Tarkuc, S., Sahmetlioglu, E., Tanyeli, C., Akhmedov, I.M.,
and Toppare, L., Opt. Mater., 2008, vol. 30, pp. 1489–
1494.
17. Ak, M., Şahmetlioğlu, E., and Toppare, L., J. Electro-
anal. Chem., 2008, vol. 621, pp. 55–61.
18. Bobacka, J., Anal. Chem., 1999, vol. 71, pp. 4932–4937.
19. Skotheim, T.A., Elsenbaumer, R.L., and Reynolds, J.R.,
Handbook of Conducting Polymers, New York: Marcel
Dekker, 1998, 3 ed.
REFERENCES
1. Glenis, S., Benz, M., Legoff, E., Schindler, J.L.,
Kannewurf, C.R., and Kanatzidis, M.G., J. Am. Chem.
Soc., 1993, vol. 115, pp. 12519–12525.
2. Turac, E., Varol, R., Ak, M., Sahmetlioglu, E., and
Toppare, L., Des. Monomers Polym., 2008, vol. 11,
pp. 309–317.
3. Kümbül, A., Turaç, E., Dursun, T., and Şahmetlioğlu, E.,
Chem. Pap., 2009, vol. 64, no. 1, pp. 114–117.
4. Tarkuc, S., Sahmetlioglu, E., Tanyeli, C., Akhmedov, I.M.,
and Toppare, L., Electrochim. Acta., 2006, vol. 51,
pp. 5412–5419.
5. Tarkuc, S., Sahmetlioglu, E., Tanyeli, C., Akhmedov, I.M.,
and Toppare, L., Sensor. Actuat. B-Chem., 2007,
vol. 121, pp. 622–628.
6. Hillman, A.R. and Mallen, E.F., J. Electroanal.
Chem.,1990, vol. 281, pp. 109–124.
20. McNeill, R., Weiss, D.E., and Willis, D., Aust. J.
Chem., 1965, vol. 18, pp. 477–486.
21. Diaz, A.F., Kanazawa, K.K., and Gadrini, G P., J. Am.
Chem. Soc. Chem. Commun., 1979, pp. 635–636.
22. Wang, H.L., Toppare, L., and Femandez, J.E.
Macromolecules,1990, vol. 23, pp. 1053–1059.
23. Dogan, S., Toppare, L., and Akbulut, U., Synthetic Met.,
1992, vol. 53, pp. 29–35.
24. Selampınar, F., Akbulut, U., Yalcın, T., Suzer, S., and
Toppare, L., Synthetic Met., 1994, vol. 62, pp. 201–206.
25. Jonas, F. and Schrader, L., Synthetic Met., 1991, vol. 41,
pp. 831–836.
26. Dietrich, M., Heinze, J., Heywang, G., and Jonas, F.,
J. Electroanal. Chem., 1994, vol. 369, pp. 87–92.
27. Sessler, J. L., An, D., Cho, W.S., Lynch, V., and
Marquez, J., Chem-Eur. J. 2005, vol. 11, pp. 2001–
2011.
7. Pei, Q., Yu,G., Zhang, C., Yang, Y., and Heeger, A.J.,
Science, 1995, vol. 269, pp. 1086–1088.
28. Nakazaki, J., Matsushita, M.M., Izuoka, A., and
Sugawara, T., Mol. Cryst. Liq. Cryst., 1997, vol. 306,
pp. 81–88.
8. Johansson, T., Mammo, W., Andersson, M.R., and
Inganäs, O., Chem. Mater., 1999, vol. 11, pp. 3133–
3139.
29. Varis, S., Ak, M., Tanyeli, C., Akhmedov, I.M., and
Toppare, L., J. Electroanal. Chem., 2007, vol. 603,
no. 1, pp. 8–14.
9. Pei, Q., Jarvinen, H., Osterholm, J.E., Inganäs, O., and
Laakso, J., Macromolecules, 1992, vol. 25, pp. 4297–
4301.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 12 2011