Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone
The method of impedance spectroscopy was used to study the conductivity of the films of sodium salt of 2-methyl-5-phenylpenten-2-3-5-dione (Namphрd) and polymer based on it that were prepared using drip application from various solvents. It was shown that the use of different solvents when applying...
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Інститут фізики напівпровідників імені В.Є. Лашкарьова НАН України
2019
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| Cite this: | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone / O.S. Berezhnytska, O.K. Trunova, А.О. Gudyma, А.B. Smirnov, O.B. Okhrimenko, Yu.Yu. Bacherikov // Semiconductor Physics Quantum Electronics & Optoelectronics. — 2019. — Т. 22, № 4. — С. 391-396. — Бібліогр.: 18 назв. — англ. |
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| author | Berezhnytska, O.S. Trunova, O.K. Gudyma, А.О. Smirnov, А.B. Okhrimenko, O.B. Bacherikov, Yu.Yu. |
| author_facet | Berezhnytska, O.S. Trunova, O.K. Gudyma, А.О. Smirnov, А.B. Okhrimenko, O.B. Bacherikov, Yu.Yu. |
| citation_txt | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone / O.S. Berezhnytska, O.K. Trunova, А.О. Gudyma, А.B. Smirnov, O.B. Okhrimenko, Yu.Yu. Bacherikov // Semiconductor Physics Quantum Electronics & Optoelectronics. — 2019. — Т. 22, № 4. — С. 391-396. — Бібліогр.: 18 назв. — англ. |
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| container_title | Semiconductor Physics Quantum Electronics & Optoelectronics |
| description | The method of impedance spectroscopy was used to study the conductivity of the films of sodium salt of 2-methyl-5-phenylpenten-2-3-5-dione (Namphрd) and polymer based on it that were prepared using drip application from various solvents. It was shown that the use of different solvents when applying films from solutions allows to obtain materials with different types of conductivity due to the specific solvation of the materials.
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| first_indexed | 2026-03-23T18:59:09Z |
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ISSN 1560-8034, 1605-6582 (On-line), SPQEO, 2019. V. 22, N 4. P. 391-396.
© 2019, V. Lashkaryov Institute of Semiconductor Physics, National Academy of Sciences of Ukraine
391
Semiconductor physics
Conductivity of molecular semiconductor material
based on monomeric and polymeric methacroylacetophenone
O.S. Berezhnytska
1
, O.K. Trunova
1
, А.О. Gudyma
1
, А.B. Smirnov
2
, O.B. Okhrimenko
2*
, Yu.Yu. Bacherikov
2
1
V. Vernadsky Institute of General and Inorganic Chemistry, NAS of Ukraine,
32/34, Palladin prospect, 03142 Kyiv, Ukraine
2
V. Lashkaryov Institute of Semiconductor Physics, NAS of Ukraine
41, prospect Nauky, 03680 Kyiv, Ukraine,
*E-mail: olga@isp.kiev.ua
Abstract. The method of impedance spectroscopy was used to study the conductivity of the
films of sodium salt of 2-methyl-5-phenylpenten-2-3-5-dione (Namphрd) and polymer
based on it that were prepared using drip application from various solvents. It was shown
that the use of different solvents when applying films from solutions allows to obtain
materials with different types of conductivity due to the specific solvation of the materials.
Keywords: impedance spectroscopy, monomer, polymer, conductivity, organic (molecular)
semiconductors, methacroylacetophenone.
https://doi.org/10.15407/spqeo22.04.391
PACS 73.61.-r, 81.05.Fb, 81.15.-z
Manuscript received 01.09.19; revised version received 18.09.19; accepted for publication
29.10.19; published online 08.11.19.
1. Introduction
In recent years, intensive researches performed in the
field of semiconductor physics and microelectronics have
been aimed at expanding the circle of semiconductor
materials with new properties, in particular, at the
development of such a field as molecular electronics.
The increased interest in organic semiconductors is
associated primarily with relative simplicity of
technology and the low cost of the obtained material.
Moreover, the use of organic molecules in various
configurations opens wide possibilities for modifying
both the electrophysical and optical properties of the
material.
One of the varieties of semiconductor materials is
organic (molecular) semiconductors – wide class of
substances related by the type of bond to molecular
compounds and possessing noticeable electrical
conductivity. These include, for example, molecular
crystals, organic dyes, charge-transfer molecular
complexes, biological substances (chlorophyll,
β-carotene), ion-radical salts, as well as polymers.
An important parameter characterizing the speed of
organic semiconductors is the mobility of charge carriers.
Now, obtained are organic semiconductors in which this
parameter is comparable in its magnitude with the
mobility of charge carriers in amorphous silicon (a-Si),
but so far, it is much lower than that in polycrystalline
silicon (p-Si).
The electrical conductivity of organic
semiconductors, as a rule, is low (~10
–10
Ohm
–1⋅сm–1
),
and the mobility of charge carriers greatly increases
under the action of light (10
3
–10
5
сm
2
/V·s). However,
some organic semiconductors (crystals and polymers
based on tetracyanquinodimethane (TCNQ) compounds,
complexes based on phthalocyanine, perylene,
violanthrene, etc.) have the electrical conductivity at
room temperature comparable with that of classical
inorganic semiconductors.
Molecular electronics based on organic semi-
conductors is an important subject for various researches
and development. This trend can be explained by the fact
that organic semiconductors seem to be promising
material for use as an active layer in optoelectronic
devices, namely: field-effect transistors, LEDs, and
photocells [1-3]. Materials based on β-diketones, their
derivatives, and coordination compounds for these
devices are mainly used in the form of thin-film
structures from successively deposited layers of the
studied materials [4-6].
Deposition of films from various solvents makes it
possible to trace the influence of the solvent on the type
of conductivity, structure, uniformity, and homogeneity
of the obtained film coatings. The study of the electro-
physical properties of these materials, in particular,
determination of the sign of the main charge carriers in
these materials, is actual to identify the features of
functioning of the elements of organic electronics,
SPQEO, 2019. V. 22, N 4. P. 391-396.
Berezhnytska O.С., Trunova O.K., Gudyma А.О. et al. Conductivity of molecular semiconductor material based …
392
selection of solvent. It should be noted that in recent
years, materials that can be used as semiconductors of
various types in planar heterostructures (organic
electroluminescent materials) have become more widely
used [5–9].
As a rule, the role of conductive materials belongs
to organic compounds in particular PEDOT:PSS, PVK,
TPD, etc. These compounds have only one type of
conductivity (n- or p). Therefore, it becomes actual to
synthesize a material that can act as semiconductor of
both n- and p-type conductivity, depending on the
solvent of which the films are deposited. Obviously, the
influence of the solvent is associated both with the
viscosity of the dispersion medium, dielectric
conductivity and, of course, with solvation effects or
specific solvation. A study of the effect of a solvent on
the type of conductivity was not previously carried out.
The aim of this work was to study the conductivity
of the films of the sodium salt of 2-methyl-5-
phenylpenten-2-3-5-dione (Namphрd) and the polymer
based on it, obtained by drip application from various
solvents.
2. Еxperimental technique
2.1. Synthesis of 2-methyl-5-phenyl-penten-1-dione-3,5
The synthesis of 2-methyl-5-phenyl-pentene-1-dione-3.5
was carried out by condensation of acetophenone and
ethyl ether of methacrylic acid according to Kleisen [10].
Into the three-necked reactor equipped with a stirrer,
reflux condenser and dropping funnel, where 0.5 mol of
sodium metal (11.5 g) and 300 cm
3
of dry diethyl ether
were placed, a solution of acetophenone 0.5 mol (59 cm
3
)
and ethyl ether of methacrylic acid 0.5 mol (63 cm
3
) was
spilled drop, this solution was pre-chilled with a mixture
of ice and salt. The reaction mixture was heated, and a
yellow precipitate was formed:
O O O
Na
OC
2
H
5
O
Na
+
After the last portion of the reagents was
introduced, the solution was stirred for 3 hours and left
at ~20 °C for 12 hours. After that, the precipitate was
filtered off, washed and dried in a dessicator over P2O5.
The yield of the final product was 76 g (~ 72%). The
sodium salt of C12H11O2Na prepared according to the
described procedure is an amorphous yellow powder
with melting temperature 216 °C.
The ligand was polymerized at 800 °C in dimethyl-
formamide at the concentration 0.03 mol/L and the
initiator concentration of 2,2'-azo-bis (isobutyronitrile) –
0.0003 mol/L in a thermostat for 4 hours. The obtained
metal polymer was precipitated from the solution with
isopropanol-2.
The purity of the synthesized unsaturated
β-diketone was determined by elemental analysis and
NMR
1
H method (Table).
The position of the CH3 proton signals differs by
~ 0.2 ppm, which indicates the presence of equilibrium
between the ketone and enol forms in the solution:
C
R1 CH
C
O O
R2
1
C
CC
R1 R2
O O
H
2
C
CC
R1 R2
O O
H
3
R3 R3 R3
R1 = –C(CH3) = CH2; R2 = –C6H5 (for Hmphpd )
The exchange between the ketone and enol forms is
rather slow – the exchange rate is less than the band
width at half maximum (0.5 Hz). The shift of the signal
of OH protons to a weak field indicates formation of an
intramolecular hydrogen bond in enol. In addition, a very
wide OH signal against the background of fairly narrow
signals of protons of CH, CH2, and CH3 groups may
indicate the presence of several potential wells in which
OH-proton can be located. A probable reason for this fact
is the competition of intra- and intermolecular hydrogen
bonding of enol.
For deposition onto glasses, the samples were
dissolved in chloroform (CHCl3), dimethylformamide
(DMFA, N(CH3)2CHO) and alcohol (C2H5OH). The
concentration of the sample was 0.03 M. On a pre-
cleaned glasses with the deposited layer of contact (Ga:In
= 50:50 wt.%), a concentrated solution of the substance
was spilled drop and left to dry completely.
Table. Elemental analysis and NMR 1Н data for unsaturated β-diketones.
Element, calculated
(determined), % Сompound
С Н Na
NMR
1
Н (CDCl3),
δ (ppm)
C12H11O2Na
68.55
(68.31)
5.28
(5.20)
10.82
(10.94)
0.97–1.15 (mult., 2Н, C–CH 2–);
1.98 (single, 3H, CH 3);
3.55–3.62 (single, 1H, =CH–);
7.05–7.96 (mult. ext., 5H, Ph),
16.08 (single wide, 4Н, ОН)
SPQEO, 2019. V. 22, N 4. P. 391-396.
Berezhnytska O.С., Trunova O.K., Gudyma А.О. et al. Conductivity of molecular semiconductor material based …
393
2.2. Impedance spectroscopy technique
To perform electrophysical studies, the impedance
spectrometry technique was used. The impedance
characteristics of the samples were determined using
“LCR-819”-meter in the range 1…100 kHz with the
sinusoidal signal amplitude close to 120 mV. From the
technical viewpoint, this method consists of measuring
the frequency dependences of the real (Z'(ω)) and
imaginary (Z''(ω)) components of the complex
impedance inherent to the material under study. As a
rule, the obtained frequency characteristics (Z'(ω) and
Z''(ω)) are approximated using an equivalent electric
circuit, by selecting its active and reactive elements – R,
L, C. For a material homogeneous in its physical
properties, the hodograph, as a rule, has the shape of a
semicircle with a diameter R and center on the z-axis
passing through the origin, which corresponds to the
equivalent electrical circuit of a parallel RC circuit.
3. Experimental results and discussion
The impedance hodograph in the coordinates (Z'', Z') in
the shape of Nyquist diagrams is shown in Fig. 1.
From the mentioned above, the choice of an
equivalent electrical circuit (R, L, C) should be based on
the presence of certain physical properties. In our case,
the interpretation of the obtained hodographs (Fig. 1) is
ambiguous in consequence of the uncertainty in the
choice of the dominant technological process of
preparing the samples and reflects rather the
polarizability of the synthesized medium.
This behavior at low frequencies 10…10
2
Hz
indicates a characteristic process of charge transfer in the
obtained films, which is associated with ion migration.
Some analogy can be drawn with ion-migration
polarization that is inherent to dielectrics. It can be
assumed that for our case, the synthesized films will have
various types of conductivity [13], which is caused by
specific solvation. As you know, the influence of a
solvent on the electrical conductivity primarily consists
in the influence of its viscosity, dielectric function and
specific interaction with ions (specific solvation).
The viscosity forces of the solvent inhibit motion of
ions. The dielectric properties of the medium affect the
effective strength of electric field and interionic potential.
The latter values effect not only the velocity of ions,
but also the attraction between contralateral ions and,
-1400 -700 0
-0.002
0.000
0.002
Im
(Z
),
O
h
m
Re(Z), Ohm
TGFII
-5000 0 5000
-0.10
-0.05
0.00
Im
(Z
),
O
h
m
Re(Z), Ohm
C2H5OH(II)
-1000 0 1000 2000 3000
-0.005
0.000
0.005
Im
(Z
),
O
h
m
Re(Z), Ohm
C2H5OH(I)
-3000 -2000 -1000 0
0.000
0.005
0.010
0.015
DMFA
Im
(Z
),
O
h
m
Re(Z), Ohm
Fig. 1. Nyquist diagrams of the samples.
SPQEO, 2019. V. 22, N 4. P. 391-396.
Berezhnytska O.С., Trunova O.K., Gudyma А.О. et al. Conductivity of molecular semiconductor material based …
394
0.000 0.015 0.030 0.045
-6.0x10
-10
-5.0x10
-10
-4.0x10
-10
-3.0x10
-10
-2.0x10
-10
-1.0x10
-10
E,V
I,mF
12
Fig. 2. Voltage-capacitance characteristics of monomer (1) and
polymer (2) in С2Н5ОН.
0.000 0.015 0.030 0.045
-6.0x10
-10
-5.0x10
-10
-4.0x10
-10
-3.0x10
-10
-2.0x10
-10
-1.0x10
-10
I, mF
E, V
1
2
Fig. 3. Voltage-capacitance characteristics of the polymer in
DMFA (1) and monomer in С2Н5ОН (2).
0.000 0.015 0.030 0.045
-5.0x10
-10
-4.0x10
-10
-3.0x10
-10
-2.0x10
-10
-1.0x10
-10
E,V
I,mF
Fig. 4. Voltage-capacitance characteristic of CHCl3 polymer.
therefore, the degree of their binding in pairs. Specific
solvation of ions can effect both mobility and
association. Solvate shells reduce the tendency of ions to
associate. If there are no solvate shells, interaction
between ions is enhanced. If the solvent molecule forms
associates with the studied compounds, then it is under
the influence of powerful electrostatic fields.
Therefore, in this work it will be correct to consider
the voltage-capacitance characteristics of the studied
objects. Interpretation of the measured voltage-
capacitance characteristics of all the samples was carried
out (Figs. 2 to 4). The type of conductivity of the studied
molecular semiconductor material was determined by the
shape of dependence. Being based on the nature of the
obtained dependences, we can distinguish three depen-
dences indicating p-type conductivity (Figs. 2 and 3) and
one dependence – n-type (Fig. 4), respectively [11].
The studies of monomeric and polymeric sodium
methacroylacetophenate have shown that the same type
of conductivity occurs in donor solvents, both proton and
aproton ones. As can be seen from Fig. 2, the voltage-
capacitance characteristics of the monomer and polymer
in ethanol are close, although a significant difference in
the shape and slope angle of the curve is noticeable,
which may be caused by both lower solubility and,
consequently, lower concentration of the initial polymer,
and better polymer conductivity as compared with the
monomer.
From the analysis of Fig. 3 (monomer film prepared
from alcohol and polymer film prepared from DMFA), it
is seen that the character (type, bending) of the curve is
exactly the same, which may indicate the same solvation
(type of solvation) of these compounds. Obviously, there
is a certain dependence on the concentration, so, the
solubility of monomer is better in alcohol and the
solubility of polymer in DMFA, which may indicate a
slight difference in the concentration and dispersion of
the obtained systems. The shape and size of particles
significantly influence physical characteristics of objects.
Since these films are two-dimensional nanoparticles
(only one size is in the nanometer range), it is probable
that the electrophysical properties also depend on which
group of objects they belong to: regular or irregular [14].
Despite the different nature of the solvents, as a rule,
alcohol is an electrophilic agent, but it is known that in
some cases it behaves like a nucleophile.
In the case of a film obtained from chloroform
(Fig. 4), the angle of inclination, shape of the curve are
similar to the films of DMFA and alcohol, only bending
in the opposite direction, which is probably caused by a
similar concentration of polymers in the film and indi-
cates the same electron mobility. Of all the used solvents,
chloroform (CHCl3) is the least polar electrophilic agent.
If we compare the dielectric functions of chloroform
CHCl3 and DMFA, then it is 7.5 times less than that in
DMF and 5 times lower than that in alcohol, which, of
course, affects also the mechanism of solvation [15-18].
Depending on the nature of the solvent, the type of
conductivity of the films changes, which is caused by a
different mechanism of solvation, so, in the case of the
SPQEO, 2019. V. 22, N 4. P. 391-396.
Berezhnytska O.С., Trunova O.K., Gudyma А.О. et al. Conductivity of molecular semiconductor material based …
395
nucleophilic mechanism of solvation (DMFA, alcohol),
we have p-type of conductivity, and in the case of
electrophilic (chloroform) – n-type.
For known values of the dielectric function inherent
to solvents and chemical components (ε = 4…40 [12]),
the concentration in the depletion region Nf and barrier
capacitance Cs are related by the simple expression Nf =
= (Cs/S)
2
(4kBT)/(εε0e
2
), where kB is the Boltzmann
constant, T = 300 K, ε – dielectric function of materials
(films), ε0 – vacuum electric constant; e – electron
charge, S = 0.01 m
2
– area of the sample. Molecular
semiconductor films are characterized by the value of Nf
that varies within the range 4.7 10
12
…4.7 10
11
m
–2
.
Obviously, the value of Nf reflects the fixed charge of the
semiconductor material based on monomeric and poly-
meric methacroylacetophenone that is under studying.
4. Conclusions
Thus, the studies have shown that the use of various
solvents in the deposition of films from solutions of the
monomer and polymer compounds allows to obtain
materials with various types of conductivity, which is
caused by specific solvation of these materials.
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Berezhnytska O.С., Trunova O.K., Gudyma А.О. et al. Conductivity of molecular semiconductor material based …
396
Authors and CV
O.K. Trunova, Doctor of Chemistry,
Senior Fellow (Associate Professor),
Head of Department for Heterophase
Synthesis of Inorganic Compounds
and Materials, V.I. Vernadsky
Institute of General and Inorganic
Chemistry of the National Academy
of Sciences of Ukraine. The area
of her scientific interests includes
inorganic chemistry, dielectric coatings, polymer
nanostructured films, solid state chemistry, technology
and production of functional materials.
O.S. Berezhnytska, PhD of Chemi-
stry, Senior researcher at the Depart-
ment for Heterophase Synthesis of
Inorganic Compounds and Materials,
V.I. Vernadsky Institute of General
and Inorganic Chemistry, NAS of Uk-
raine, associate professor of Faculty
of Chemical Technology of National
Technical University of Ukraine
“Igor Sikorsky Kyiv Polytechnic
Institute”. The area of her scientific interests is
luminescent materials based on lanthanide complexes.
A.O. Gudyma, PhD of Chemistry,
Senior researcher at the Department
for Heterophase Synthesis of
Inorganic Compounds and Materials,
V.I. Vernadsky Institute of General
and Inorganic Chemistry, NAS of
Ukraine. The area of his scientific
interests includes organic and inorga-
nic chemistry, technology and produc-
tion of functional materials.
A.B. Smirnov, Doctor of Sciences in
Physics and Mathematics, Senior
researcher of the Department of
Physics and Technology of low-
dimensional systems at the V. Lash-
karyov Institute of Semiconductor
Physics, NAS of Ukraine. Specia-
lization – semiconductor physics.
Other fields – photoelectronics, inter-
action of laser radiation with solids,
IR and THz detectors, coatings, multiband radiation de-
tector based on HgCdTe heterostructure, nanoscale pattern
formation on the surface of semiconductors produced by
ion bombardment.
Yu.Yu. Bacherikov, Doctor of
Sciences in Physics and Mathematics,
Leading scientific collaborator at the
V. Lashkaryov Institute of Semi-
conductor Physics, NAS of Ukraine.
Authored over 330 publications, 6
patents, 1 monograph. The area of his
scientific interests includes physics
and applications of wide-band semi-
conductor compounds and devices
based on them.
O.B. Okhrimenko, Doctor of
Sciences in Physics and Mathematics,
Leading scientific collaborator at the
V. Lashkaryov Institute of Semicon-
ductor Physics, NAS of Ukraine.
Authored over 150 publications, 1 pa-
tent, 1 monograph. The area of her
scientific interests includes investiga-
tion of the patterns and physical me-
chanisms of formation and rearrange-
ment of the defect-impurity system of the thin-film dielec-
tric-semiconductor structures, depending on the techno-
logy of obtaining, the composition of the thin film, addi-
tional processing and the introduction of buffer layers.
|
| id | nasplib_isofts_kiev_ua-123456789-215593 |
| institution | Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| issn | 1560-8034 |
| language | English |
| last_indexed | 2026-03-23T19:08:20Z |
| publishDate | 2019 |
| publisher | Інститут фізики напівпровідників імені В.Є. Лашкарьова НАН України |
| record_format | dspace |
| spelling | Berezhnytska, O.S. Trunova, O.K. Gudyma, А.О. Smirnov, А.B. Okhrimenko, O.B. Bacherikov, Yu.Yu. 2026-03-20T08:45:16Z 2019 Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone / O.S. Berezhnytska, O.K. Trunova, А.О. Gudyma, А.B. Smirnov, O.B. Okhrimenko, Yu.Yu. Bacherikov // Semiconductor Physics Quantum Electronics & Optoelectronics. — 2019. — Т. 22, № 4. — С. 391-396. — Бібліогр.: 18 назв. — англ. 1560-8034 PACS: 73.61.-r, 81.05.Fb, 81.15.-z https://nasplib.isofts.kiev.ua/handle/123456789/215593 https://doi.org/10.15407/spqeo22.04.391 The method of impedance spectroscopy was used to study the conductivity of the films of sodium salt of 2-methyl-5-phenylpenten-2-3-5-dione (Namphрd) and polymer based on it that were prepared using drip application from various solvents. It was shown that the use of different solvents when applying films from solutions allows to obtain materials with different types of conductivity due to the specific solvation of the materials. en Інститут фізики напівпровідників імені В.Є. Лашкарьова НАН України Semiconductor Physics Quantum Electronics & Optoelectronics Semiconductor Physics Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone Article published earlier |
| spellingShingle | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone Berezhnytska, O.S. Trunova, O.K. Gudyma, А.О. Smirnov, А.B. Okhrimenko, O.B. Bacherikov, Yu.Yu. Semiconductor Physics |
| title | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone |
| title_full | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone |
| title_fullStr | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone |
| title_full_unstemmed | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone |
| title_short | Conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone |
| title_sort | conductivity of molecular semiconductor material based on monomeric and polymeric methacroylacetophenone |
| topic | Semiconductor Physics |
| topic_facet | Semiconductor Physics |
| url | https://nasplib.isofts.kiev.ua/handle/123456789/215593 |
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