New tetrathiafulvalenes containing carbazole and 1,3,5-triazine fragments: Synthesis, electro-chemical and optical properties

Article abstract of DOI:10.1007/s10593-014-1522-3

New tetrathiafulvalenes, containing carbazole and 1,3,5-triazine fragments added to the tetrathia-fulvalene ring by means of a S-CH₂-CH ₂-O bridge, were synthesized. The electrochemical properties of the initial compounds and of the final products were investigated by cyclic voltammetry. The optical characteristics of their solutions were studied by UV absorption spectroscopy and fluorescence spectroscopy.

Full text of DOI:10.1007/s10593-014-1522-3

Chemistry of Heterocyclic Compounds, Vol. 50, No. 5, August, 2014 (Russian Original Vol. 50, No. 5, May, 2014)
NEW TETRATHIAFULVALENES CONTAINING CARBAZOLE
AND 1,3,5-TRIAZINE FRAGMENTS: SYNTHESIS, ELECTRO-
CHEMICAL AND OPTICAL PROPERTIES
1
1
2
1
E. A. Ignatenko *, A. A. Gorbunov , E. V. Shklyaeva , and G. G. Abashev
New tetrathiafulvalenes, containing carbazole and 1,3,5-triazine fragments added to the tetrathia-
fulvalene ring by means of a S–CH –CH –O bridge, were synthesized. The electrochemical properties
2
2
of the initial compounds and of the final products were investigated by cyclic voltammetry. The optical
characteristics of their solutions were studied by UV absorption spectroscopy and fluorescence
spectroscopy.
Keywords: conjugated polymer, tetrathiafulvalene, cyclic voltammetry, electrochemical oxidation,
luminescence.
The synthesis and investigation of electroactive organic compounds is a pressing problem for
contemporary chemistry and physics. The route to the synthesis of conjugated monomers and polymers,
containing simultaneously electron-rich and electron-deficient heterocyclic systems [1-2], has been developed
vigorously owing to the considerable potential for use, e.g., in organic light-emitting diodes and solar batteries
[
3-7]. One of the possible methods to give new properties to the conjugated polymers is to include structurally
diverse electroactive heterocyclic fragments such as tetrathiafulvalenes (TTFs) in the initial monomer [1-14].
The capability of TTF for reversible two-electron oxidation to the radical cation and dication at comparatively
low potentials presents the possibility of creating from them materials that react to change in the potential of the
medium and can also accumulate charge. This makes it possible to use TTFs in the manufacture of
chemosensors [15-17], batteries [18], and organic field-effect transistors [19-21].
The present work describes the synthesis of substituted triazines 1 and 2, which contain an electron-rich
carbazole substituent at position 2 of the triazine ring and in which the tetrathiafulvalene fragments are added at
positions 4 and 6 through a 2-sulfanylethoxy bridge. In order to fulfill this task we used a convergent method of
synthesis in which the concluding stage involved the interaction of previously synthesized tetrathiafulvalene
derivatives 3 and 4, containing one cyanoethyl protecting group at one of the sulfur atoms, with [4,6-bis(2-chloro-
ethoxy)-1,3,5-triazin-2-yl]-9H-carbazole (5) according to the method developed by Becher and co-workers [22]
(
Scheme 1).
_
*
______
To whom correspondence should be addressed, e-mail: info@itch.perm.ru.
1
Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, 3 Akademika Koroleva St.,
Perm 614013, Russia.
2
Natural Science Institute, Perm State University, 4 Genkel St., Perm 614990, Russia; e-mail: gabashev@psu.ru.
_
________________________________________________________________________________________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 752-760, May, 2014. Original
article submitted April 3, 2014.
009-3122/14/5005-0691©2014 Springer Science+Business Media New York
0
691

In order to obtain the required triazine 5, 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (6) was
synthesized by the substitution of one chlorine atom in cyanuric chloride by carbazolyllithium in THF
(
Scheme 1). The structure of the triazine 6 was confirmed by the mass spectrometry and elemental analysis data
1
and also by the data from H NMR spectroscopy. (All the signals of the CH protons were shifted downfield by
an average of 0.4 ppm in comparison with the spectrum of unsubstituted carbazole.) Further reaction of this
triazine with 2 equivalents of 2-chloroethanol by refluxing in acetone in the presence of K CO led to
2
3
substitution of the two remaining chlorine atoms and the formation of the chloroethoxy derivative 5. The
targeted compounds were obtained by reaction of the triazine 5 with the potassium thiolates formed in situ
during elimination of the cyanoethyl group from compounds 3 and 4.
Scheme 1
Cl
N
N
n-BuLi
Cl
N
Cl
THF
THF
room temp., 30 min
, 6 h
N
H
N
0
°C, 30 min
Li

ClCH CH OH
2
2
3
K CO
2
N
N
Me CO
2
N
N
N
N

, 10 h
Cl
Cl
Cl
O
N
O
Cl
N
6
5
1
+
1
R S
SCH CH CN
S K
2
2
R S
S
S
KOH
S
S
S
5
2
S
S
DMF, MeOH
DMF
0°C
2
S
R S
SMe
SMe
R S
2
0°C, 30 min
4
3, 4
N
N
N
O
N
1
1
R S
S
S
SR
S
S
S
S
O
S
S
S
S
2
2
R S
SMe
MeS
SR
1, 2
1
2
1
2
1
, 3 R = R = Me; 2, 4 R + R = CH CH
2
2
The second group of starting compounds used in the reaction (TTF 3 [23] and 4 [11, 22, 24]) was
obtained by cross coupling of the respective 4,5-disubstituted 1,3-dithiol-2-ones 7 and 8 [25] with 3-{[5-(methyl-
sulfanyl)-2-thioxo-1,3-dithiol-4-yl]sulfanyl}propionitrile (9) [26] by refluxing in triethyl phosphite [27]. The
4
,5-disubstituted 1,3-dithiol-2-thiones 11 and 12 [25, 28] and 13 [29-30] required for the production of 1,3-di-
thiol-2-ones 7 and 8 were synthesized by the reaction of the zinc dithiolate complex 10 [28] with the necessary
number of equivalents of the respective alkyl halide. Compound 9 [26] was obtained by Becher's method [22]
from 3,3'-[2-thioxo-1,3-dithiol-4,5-diyl]disulfanediyldipropionitrile (13) by substitution of the cyanoethyl
protecting group by methyl (Scheme 2).
6
92

Scheme 2
BrCH CH CN,
2
2
1
2
2
–
SR
S
S
S
S
S
Zn
S
S
S
S
MeI or BrCH CH Br
2
2
+
2
[NEt4]
S
S
S
Me CO, , 6 h
2
S
SR
1
0
11–13
1
2
SR
S
Hg(OAc)2
1
1, 12
O
AcOH, 
1
S
7
R S
SCH CH CN
2 2
SR
S
S
S
P(OEt)3
, 8

CsOHH O (1 equiv.)
2
2
S(CH ) CN
S
S
2 2
R S
SMe
MeI (1 equiv.)
13
S
3, 4
Ar, MeOH
0°C, 30 min
S
SMe
4
9
1
1
2
2
1
2
3
, 7, 11 R = R = Me; 4, 8, 12 R + R = CH CH ; 13 R = R = CH CH CN
2
2
2
2
Thus, the synthesis resulted in the formation of compounds 1 and 2 representing an assembly of
heterocycles with general structure D AD' the core of which is the electron-withdrawing triazine fragment (A)
2
surrounded by electron-donating substituents. One of them (the carbazole, D') is capable of polymerizing
electrochemically, while the other two TTF fragments (D) can form ordered stacks during the electrochemical
oxidation process thereby forming the spatial structure in the obtained polymer.
The data from electrochemical measurements obtained for compounds 1-6 by cyclic voltammetry are
presented in Table 1.
On account of the presence of the strongly electron-withdrawing triazine fragment attached to the
carbazole part of the molecule of compounds 5 and 6 they have very high oxidation potentials E (Fig. 1).
ox
1
The first oxidation potential (E ) corresponds to the potential for the carbazolium radical cation
formation, and the second potential (E ) corresponds to the potential for the dication formation. Substitution of
ox
2
ox
the chlorine atom in compound 6 by a 2-chloroethoxy group leads to a slight decrease of the oxidation
potentials in compound 5. On account of the decrease in the electron density of the π-system of the carbazole
resulting from the electron-withdrawing action of the triazine fragment, electrochemical polymerization
becomes a problem, and polymeric films were not therefore formed on the working electrode surface.
Compounds 1 and 2 are characterized by the presence of two reversible waves of oxidation to the
1
1
2
2
radical cation (E /E ) and the dication (E /E ) belonging to oxidation–reduction of the tetrathiafulvalene
ox
red
ox
red
part of the molecule, and this affords additional evidence for the structure of the obtained compounds (Fig. 2).
TABLE 1. The Redox Potentials of Compounds 1-6
Com-
pound
1
2
3
4
1
2
E
ox , mV
E
ox , mV
E
ox , mV
E
ox , mV
E
red , mV
E
red , mV
1
2
3
4
5
6
706
885
682
667
2246
2314
1129
1172
1053
1066
3112
3232
1455
2352
―
3032
3336
―
530
676
537
544
2300
2325
894
936
834
922
―
―
―
―
―
―
―
―
6
93

-3
Fig. 1. Cyclic voltammogram (CVA) of compound 5 (10 M) in CH Cl , supporting electrolyte Bu NPF
2
2
4
6
(
0.1 M), potential sweep rate 100 mV/s, six cycles.
From the data in Table 1 it is seen that the oxidation–reduction potentials of TTFs 1 and 2 are rather
higher than those of the initial TTFs 3 and 4 measured under the same conditions and with the same equipment.
Moreover, the CVAs of tetrathiafulvalenes 1 and 2 contain two irreversible oxidation peaks in the region of high
3
4
potentials (Eox and Ered ) belonging to oxidation of the carbazole fragment of the molecule. The current strength
increases during the sweep from cycle to cycle in the region up to 1300 mV but decreases with further increase
of potential. Growth of polymeric films on the surface of the working electrode was also not observed.
The optical properties of all the compounds were studied for their solutions in chloroform (Table 2), and
HOMO-LUMO energy band gap E was calculated on the basis of the longest absorption wavelength λonset by
g
means of the equation E = 1240/λonset, eV [31].
g
-3
Fig. 2. Cyclic voltammogram of compound 2 (10 M) in CH Cl , supporting electrolyte Bu NPF (0.1 M),
2
2
4
6
potential sweep rate 100 mV/s, 12 cycles.
In the UV spectra of the triazines 6 and 5 there are three absorption bands in the region of 250-322 nm
the wavelengths of the λ1 , λ2 , and λ3 maxima), and there is also one strong fluorescence peak at 492 and
43 nm, respectively. The initial TTFs 3 and 4 absorb in the region of 252-300 nm and have two absorption
abs
abs
abs
(
4
maxima. In the UV spectra of TTFs 1 and 2 there are three absorption maxima as also in the spectra of the initial
triazines 5 and 6. Solutions of the initial triazines 6 and 5 have maximum optical density (D), and solutions of
the initial TTFs 3 and 4 have minimal optical density. The fluorescence spectra of TTFs 1 and 2 contain three
emi
emi
emi
emi
emission bands (the wavelengths of the λ3 , λ2 , and λ1 maxima). Here the λ3 emission band can be
assigned unambiguously to the tetrathiafulvalene part of compounds 1 and 2 (Fig. 3).
6
94

TABLE 2. Optical Properties of Compounds 1-6
abs
abs
abs
λ
1
,
λ
2
,
λ
3
,
emi
emi
emi
Com-
pound
λ
nm
onset
,
λ
1
,
λ
2
,
λ
3
,
E
g
,
nm
D)
nm
(D)
nm
(D)
Δ, nm
nm
nm
nm
eV
(
1
2
3
4
5
6
243 (2.1) 290 (2.4) 322 (1.4)
242 (2.2) 288 (2.3) 314 (1.9)
496
502
389
375
330
360
445
444
445
451
443
492
524
496
639
640
―
636
637
―
123
130
145
157
133
170
2.50
2.47
3.18
3.30
3.75
3.44
252 (2.1) 300 (2.1)
247 (2.0) 294 (1.8)
―
―
―
248 (1.6) 279 (2.5) 310 (2.7)
250 (1.8) 279 (2.6) 322 (2.9)
―
―
―
From Table 2 it is seen that the Stokes shift (∆) was extremely high in all cases and was almost identical
(
~130 nm) with exception of the triazine 6, for which it amounted to 170 nm. The initial triazines 6 and 5 have
opt
the largest values of HOMO-LUMO gap Eg (~3.6 eV), whereas the value for the TTFs 1 and 2 amounted to
~
2.5 eV.
Fig. 3. Absorption and fluorescence spectra of compounds 1 and 2.
From the results of the investigation it is clear that the triazine fragment has a large effect on the
electrochemical behavior of the obtained systems. Thus, compounds 1, 2, 5, and 6 are not polymerized
electrochemically although they contain carbazole, a heterocycle whose presence in the structure of a compound
almost always leads to its polymerization. Moreover, the presence of the triazine ring in the structure of the
obtained compounds led to the result that the tetrathiafulvalene fragments were oxidized at uncharacteristically
3
4
high potentials. The very high oxidation potentials of the carbazole ring (Eox and E , Table 1) can also be
ox
explained by the presence of the electron-withdrawing triazine ring.
On the other hand, the extremely low band gap energy values (E ) of the obtained TTF-substituted
g
triazines 1 and 2 (~2.5 eV) make these compounds promising for use in organic electronics. Thus, the above-
mentioned paper [3] describes the synthesis of new effective pale-blue emitters based on a substituted 1,3,5-tri-
azine that has a similar electronic structure (D AD') with the thienyl and triphenylamino groups as donating
2
components. The average value of the band gap energy (E ) for these compounds amounted to 2.8 eV. The
g
authors constructed and tested light-emitting devices with these compounds as emission layer and investigated
their light-emitting characteristics. Dendrimeric triazine compounds containing branched aromatic structures are
6
95

known. The experimentally obtained values of band gaps for these compounds are also close to the E values of
g
the compounds that we obtained and amount to ~3 eV [32].
Our investigation resulted in the development of a method for the preparation of new conjugated donor-
acceptor heterocyclic systems that are of potential interest as materials for the manufacture of molecular
electronics devices. Two previously undescribed branched 1,3,5-triazines with electronic structure D AD',
2
containing simultaneously a carbazole and two tetrathiafulvalene fragments, were synthesized with high yields.
Their electrochemical oxidation and their optical properties were studied. The value of the HOMO-LUMO gap
energy for each of the compounds obtained in this work was calculated from the experimentally determined
longest absorption wavelengths.
EXPERIMENTAL
UV spectra were recorded on an SF-2000 spectrophotometer, cuvette length 10 mm, solvent was dry
-5
chloroform, concentration 10 M. Fluorescence spectra were recorded on a Shimadzu RF-5301 spectro-
fluorimeter. The wavelength of the excitation source was 220 nm, cuvette size 10×10 mm, solvent was dry
-5
1
chloroform, concentration 10 M. H NMR spectra were recorded in CDCl on a Varian Mercury Plus300
3
instrument (300 MHz) with HMDS as internal standard (0.037 ppm). Mass spectra were recorded on an Agilent
GC 6890N MSD 5975B chromato-mass spectrometer, EI, 70 eV. Elemental analysis was performed on a LECO
Corporation CHNS-932 instrument, and the chlorine content was determined by the Schöniger method. The
reactions and the purity of the synthesized compounds were monitored by TLC (Silufol Kavalier). The mixtures
were separated and the products were purified on a column of silica gel (Lancaster, Silica gel 60, 0.060-0.2 mm).
The column diameter and the layer height were determined by the amount of substance being purified.
The electrochemical measurements were made in methylene chloride solutions (0.001 M) at room
temperature with tetrabutylammonium hexafluorophosphate as supporting electrolyte. The cyclic
voltammograms were recorded on a P-8 potentiostat with a Modul EM-04 electrochemical sensor in a three-
electrode electrochemical cell with a glassy carbon working electrode, a platinum auxiliary electrode, and a
silver chloride reference electrode. The potential sweep rate was 100 mV/s.
3
-{[4',5,5'-Tris(methylsulfanyl)tetrathiafulvalen-4-yl]sulfanyl}propionitrile (3). A solution of a
mixture of compound 7 (1.00 g, 4.76 mmol) and compound 9 (1.39 g, 5.24 mmol) in triethyl phosphite (10 ml)
was deaerated with argon for 15 min at room temperature. It was then refluxed for 1 h and cooled, and the
excess of triethyl phosphite was removed by evaporation. The residue was chromatographed on a column filled
with silica gel. The symmetrical TTFs produced in the homodimerization process were first separated with a 1:1
mixture of CH Cl and hexane, and after their separation the reaction product TTF 3 was isolated with
2
2
methylene chloride. Compound 3 was further purified by recrystallization from acetone. Yield 0.50 g (25%).
1
Finely crystalline red powder, mp 107-109°C (mp 102-104°C (toluene–hexane) [23]). H NMR spectrum, δ,
ppm (J, Hz): 2.42 (6H, s, 2SCH
3
); 2.53 (3H, s, SCH
agrees with published data [23]).
-(4,6-Dichloro-1,3,5-triazin-2-yl)-9H-carbazole (6). A 2 M solution of n-BuLi in hexane (4.3 ml,
.5 mmol) was added dropwise to a solution of carbazole (1.42 g, 8.5 mmol) in dry THF (50 ml) that had
3
); 2.69 (2Н, t, J = 7.2, SCH
2
); 3.02 (2H, t, J = 7.2, CH
2
CN)
(
9
8
previously been deaerated with argon and cooled to 0°C. The mixture was stirred at the same temperature for 30
min and was then added to a solution of 2,4,6-trichloro-1,3,5-triazine (1.56 g, 8.5 mmol) in dry THF (50 ml)
that had been deaerated with argon. The obtained reaction mixture was kept at room temperature for 30 min and
was then refluxed for 6 h and filtered. The filtrate was evaporated, and the residue was washed with acetone (50
1
ml). Yield 2.26 g (85%). Finely crystalline colorless powder, mp 255-256°C. H NMR spectrum, δ, ppm (J,
Hz): 7.45 (2Н, td, J = 7.2, J = 0.9, Н-3,6); 7.53 (2Н, td, J = 7.5, J = 1.5, Н-2,7); 7.99 (2Н, dd, J = 7.5, J = 0.9,
+
Н-1,8); 8.85 (2Н, d, J = 8.4, Н-4,5). Mass spectrum, m/z (Irel, %): 316 (65), 315 (25), 314 [М] (100), 192 (17),
6
96

1
66 (20), 140 (18). Found, %: С 57.29; H 2.58; Cl 22.18; N 17.20. C15
Cl 22.50; N 17.78.
-[4,6-Bis(2-chloroethoxy)-1,3,5-triazin-2-yl]-9H-carbazole (5). A mixture of triazine 6 (0.75 g,
H
8
Cl
2
N . Calculated, %: С 57.17; H 2.56;
4
9
2
.6 mmol), 2-chloroethanol (4.20 g, 52.0 mmol), and K CO (1.81 g, 13.0 mmol) in acetone (50 ml) was
2
3
refluxed for 10 h. The mixture was filtered, the filtrate was evaporated, and the residue was chromatographed on
a column (eluent 1:1 CH Cl –n-hexane). Yield 0.83 g (80%). Finely crystalline colorless powder, mp 172-
2
2
1
1
73°C. H NMR spectrum, δ, ppm (J, Hz): 3.93 (4Н, t, J = 6.3, 2CH
2
Cl); 4.80 (4H, t, J = 6.0, 2OCH ); 7.40
2
(
2Н, td, J = 7.2, J = 0.9, Н-3,6); 7.51 (2Н, td, J = 7.2, J = 1.5, Н-2,7); 8.01 (2Н, dd, J = 7.2, J = 1.2, Н-1,8);
+
8
.89 (2Н, d, J = 8.4, Н-4,5). Mass spectrum, m/z (Irel, %): 404 (65), 403 (24), 402 [М] (100), 167 (25), 166
(
15), 133 (16), 131 (50), 69 (11), 63 (23). Found, %: С 56.34; H 3.97; Cl 17.48; N 14.19. C H Cl N O .
1
9
16
2
4
2
Calculated, %: С 56.59; H 4.00; Cl 17.58; N 13.89.
9
-[4,6-Bis({2-[4',5,5'-tris(methylsulfanyl)tetrathiafulvalen-4-yl]sulfanyl}ethoxy)-1,3,5-triazin-2-yl]-
9
H-carbazole (1). A solution of KOH (0.02 g, 0.4 mmol) in dry MeOH (3 ml) was added to a solution of
compound 3 (0.17 g, 0.4 mmol) in dry DMF (30 ml) that had been deaerated with argon. The mixture was then
stirred at 20°C for 30 min, and a solution of the triazine 5 (0.08 g, 0.2 mmol) in DMF was added. The mixture
was stirred at 40°C for 6 h. It was then diluted with water and extracted with CH Cl . The extract was
2
2
evaporated and purified by column chromatography (eluent 2:1 CH Cl –hexane). Yield 0.31 g (71%). Finely
2
2
1
crystalline brown powder, mp 163-164°C. H NMR spectrum, δ, ppm (J, Hz): 2.49 (6H, s, 2SCH
SCH ); 2.53 (6H, s, 2SCH ); 3.29 (4Н, t, J = 6.3, 2SCH ); 4.79 (4H, t, J = 6.0, 2OCH ); 7.19 (2Н, t, J = 7.5,
3
); 2.52 (6H, s,
2
3
3
2
2
Н-3,6); 7.44 (2Н, t, J = 7.2, H-2,7); 7.58 (2Н, d, J = 6.6, H-1,8); 8.17 (2Н, d, J = 8.9, H-4,5). Found, %:
С 41.01; H 3.15; N 5.21; S 47.62. C H N O S . Calculated, %: С 41.16; H 3.17; N 5.19; S 47.52.
3
7
34
4
2 16
9
-[4,6-Bis(2-{[2-(5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5-(methylsulfanyl)-1,3-dithiol-
4
-yl]sulfanyl}ethoxy)-1,3,5-triazin-2-yl]-9H-carbazole (2). A solution of KOH (0.015 g, 0.3 mmol) in dry
MeOH (2 ml) was added to a solution of compound 4 (0.13 g, 0.3 mmol) in dry DMF (20 ml) that had been
deaerated with argon. The mixture was stirred at 20°C for 30 min, and a solution of triazine 5 (0.06 g,
0
.15 mmol) in DMF was then added dropwise. The mixture was stirred at 40°C for 10 h, diluted with water, and
extracted with CH Cl . The extract was evaporated, and the product was purified by chromatography (eluent 2:1
2
2
1
CH Cl –hexane). Yield 0.19 g (60%). Finely crystalline brown powder, mp 155-156°C. H NMR spectrum, δ,
ppm (J, Hz): 2.46 (6H, s, 2SCH
2
2
3
); 3.29 (8H, t, J = 3.6, 2SCH
2
CH
2
S); 3.89 (4Н, t, J = 6.3, 2SCH ); 4.80 (4H, t, J
2
=
6.0, 2OCH ); 7.18 (2Н, t, J = 7.5, H-3,6); 7.43 (2Н, t, J = 7.2, H-2,7); 7.68 (2Н, d, J = 6.1, H-1,8); 8.18 (2Н,
2
d, J = 9.1, H-4,5). Found, %: С 41.22; H 3.19; N 5.22; S 47.54. C37
H
30
N
4
2
O S16. Calculated, %: С 41.31; H 2.81;
N 5.21; S 47.69.
The work was carried out with financial support from the Russian Foundation for Basic Research
grants 14-03-00341A and 14-03-96003).
(
REFERENCES
1
2
3
.
.
.
P. Leriche, F. Piron, E. Ripaud, P. Frère, M. Allain, and J. Roncali, Tetrahedron Lett., 50, 5673 (2009).
M. Ak and L. Toppare, Mater. Chem. Phys., 114, 789 (2009).
J. Liu, M.-Y. Teng, X.-P. Zhang, K. Wang, C.-H. Li, Y.-X. Zheng, and X.-Z. You, Org. Electron., 13,
2
177 (2012).
4
5
6
.
.
.
J. Zhuang, W. Su, W. Li, Y. Zhou, Q. Shen, and M. Zhou, Org. Electron., 13, 2210 (2012).
E. Orselli, J. Maunoury, D. Bascour, and J.-P. Catinat, Org. Electron., 13, 1506 (2012).
A. Luechai, N. Pootrakulchote, T. Kengthanomma, P. Vanalabhpatana, and P. Thamyongkit, J.
Organomet. Chem., 753, 27 (2014).
7
.
J. Liu, K. Wang, X. Zhang, C. Li, and X. You, Tetrahedron, 69, 190 (2013).
6
97

8
9
.
.
G. Lai, Y. Liu, M. Li, and Y. Shen, Front. Chem. Eng. China, 3, 192 (2009).
G. G. Abashev, E. V. Shklyaeva, R. V. Syutkin, K. Yu. Lebedev, I. V. Osorgina, V. A. Romanova, and
A. Yu. Bushueva, Solid State Sci., 10, 1710 (2008).
10.
11.
12.
13.
G. G. Abashev, K. Yu. Lebedev, I. V. Osorgina, and E. V. Shklyaeva, Zh. Org. Khim., 42, 1880 (2006).
[Rus. J. Org. Chem., 42, 1873 (2006).]
G. G. Abashev, A. Yu. Bushueva, and K. Yu. Lebedev, Zh. Org. Khim., 43, 129 (2007). [Rus. J. Org.
Chem., 43, 135 (2007).]
E. V. Shklyaeva, E. A. Ignatenko, and G. G. Abashev, Zh. Org. Khim., 49, 1394 (2013). [Rus. J. Org.
Chem., 49, 1379 (2013).]
E. A. Ignatenko, P. A. Slepukhin, E. V. Shklyaeva, and G. G. Abashev, Mendeleev Commun., 22, 145
(
2012).
1
1
1
1
1
1
4.
5.
6.
7.
8.
9.
X.-C. Zhang, C.-Y. Wang, G.-Q. Lai, L. Zhang, and Y.-J. Shen, Polym. Bull., 66, 893 (2011).
S. Liang, Y. Zhao, and A. Adronov, J. Am. Chem. Soc., 136, 970 (2014).
K. A. Nielsen, Tetrahedron Lett., 53, 5616 (2012).
J. Xiong, L. Sun, Y. Liao, G.-N. Li, J.-L. Zuo, and X.-Z. You, Tetrahedron Lett., 52, 6157 (2011).
M. Kato, D. Ogi, M. Yao, and Y. Misaki, Chem. Lett., 42, 1556 (2013).
T. Marszalek, A. Nosal, R. Pfattner, J. Jung, S. Kotarba, M. Mas-Torrent, B. Krause, J. Veciana,
M. Gazicki-Lipman, C. Crickert, G. Schmidt, C. Rovira, and J. Ulanski, Org. Electron., 13, 121 (2012).
H. Jiang, X. Yang, E. Wang, Y. Fu, Y. Liu, H. Li, Z. Cui, Y. Liu, and W. Hu, Synth. Met., 161, 136
2
0.
(
2011).
2
2
1.
2.
N. Borjigin, J.-I. Nishida, S. Tokito, L. Theogarajan, and Y. Yamashita, Synth. Met., 160, 2323 (2010).
K. B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, M. Mørk, G. J. Kristensen, and J. Becher,
Synthesis, 407 (1996).
2
2
3.
4.
J. Lau, O. Simonsen, and J. Becher, Synthesis, 521 (1995).
G. G. Abashev, E. V. Shklyaeva, A. G. Tenishev, and A. B. Sheremetev, in: Prospects for Development
of Natural Sciences in High School (Proceedings of International Scientific Conference) [in Russian],
Vol. 1, Izd-vo Perm. Gos. Univ., Perm (2001), p. 15.
2
2
2
2
5.
6.
7.
8.
K. Hartke, T. Kissel, J. Quante, and R. Matusch, Chem. Ber., 113, 1898 (1980).
J. Becher, J. Lau, P. Leriche, P. Mørk, and N. Svenstrup, J. Chem. Soc., Chem. Commun., 2715 (1994).
N. Svenstrup, R. M. Rasmussen, T. K. Hansenm, and J. Becher, Synthesis, 809 (1994).
G. Steimecke, H.-J. Sieler, R. Kirmse, and E. Hoyer, Phosphorus, Sulfur Silicon Relat. Elem., 7, 49
(
1979).
G. G. Abashev, V. S. Russkikh, and E. V. Shklyaeva, in: Electronics of Organic Materials (ELORMA-
0), Proceedings of All-Union Conference [in Russian], Dombai, (1990), p. 81.
2
9.
9
3
3
0.
2.
G. G. Abashev, V. S. Russkikh, E. V. Shklyaeva, and V. I. Vladykin, Zh. Org. Khim., 31, 1705 (1995).
H. Meng, J. Zheng, A. J. Lovinger, B.-C. Wang, P. G. Van Patten, and Z. Bao, Chem. Mater., 15, 1778
(
2003).
3
2.
C. K. Kim, E. S. Song, H. J. Kim, C. Park, Y. C. Kim, J. K. Kim, J. W. Yu, and C. Kim, J. Polym. Sci.,
Part A: Polym. Chem., 44, 254 (2006).
6
98