Nucleophilic substitution in 4-bromo-5-nitrophthalonitrile: XIV. Synthesis and properties of 4,5-bis[4-(1-methyl-1-phenylethyl)phenoxy]phthalonitrile and phthalocyanines therefrom

Article abstract of DOI:10.1134/S1070363216110165

4,5-Bis[4-(1-methyl-1-phenylethyl)phenoxy]phthalonitrile was prepared by the nucleophilic substitution of the nitro group and bromine in 4-bromo-5-nitrophathalonitrile. The product was used to synthesize the corresponding octasubstituted phthalocyanine, a

Full text of DOI:10.1134/S1070363216110165

ISSN 1070-3632, Russian Journal of General Chemistry, 2016, Vol. 86, No. 11, pp. 2501–2507. © Pleiades Publishing, Ltd., 2016.
Original Russian Text © S.A. Znoiko, M.A. Serova, A.A. Uspenskaya, A.V. Zav’yalov, V.E. Maizlish, G.P. Shaposhnikov, 2016, published in Zhurnal
Obshchei Khimii, 2016, Vol. 86, No. 11, pp. 1859–1865.
Nucleophilic Substitution in 4-Bromo-5-nitrophthalonitrile:
XIV.1 Synthesis and Properties
of 4,5-Bis[4-(1-methyl-1-phenylethyl)phenoxy]phthalonitrile
and Phthalocyanines Therefrom
S. A. Znoiko*, M. A. Serova, A. A. Uspenskaya,
A. V. Zav’yalov, V. E. Maizlish, and G. P. Shaposhnikov
Research Institute of Macroheterocyclic Chemistry, Ivanovo State University of Chemical Technology,
Sheremetevskii pr. 7, Ivanovo, 153000 Russia
*e-mail: znoykosa@yandex.ru
Received May 12, 2016
Abstract—4,5-Bis[4-(1-methyl-1-phenylethyl)phenoxy]phthalonitrile was prepared by the nucleophilic substitution
of the nitro group and bromine in 4-bromo-5-nitrophathalonitrile. The product was used to synthesize the
corresponding octasubstituted phthalocyanine, as well as its magnesium, copper, zinc, cobalt, and nickel
complexes. The spectral properties of the synthesized phthalocyanines were studied.
Keywords: 4-bromo-5-nitrophthalonitrile, nucleophilic substitution, metal phthalocyanines, electronic absorption
spectra
DOI: 10.1134/S1070363216110165
At present phthalocyanines and complexes are actively
studied due to their wide practical use [2, 3]. Special
attention is attached to liquid crystalline phthalo-
cyanines [4–6] as new materials for nanotechnology
[7–9]. As both tetrasubstituted [10] and bifunctionally
substituted phthalocyanines [2] are synthesized from
the corresponding unsymmetrically substituted phthalo-
nitriles [2, 11, 12], such syntheses may form mixtures
of randomers of various structures [10, 13, 14], which
are extremely difficult to separate because of the close
physicochemical characteristics of these compounds.
At the same time, the physicochemical [15] and, in
particular, liquid crystalline properties of phthalo-
cyanines [3, 7] are quite sensitive to how uniform is
the composition of the studied substance. For instance,
the presence of randomers may affect both the
temperature parameters of the mesophase and the very
ability of the compound mesophase formation [3, 7].
The formation of randomer mixtures is commonly
prevented by prepacycle highly symmetric phthalo-
cyanines on the basis of phthalonitriles having the
same substituents in the 3- and 6- or 4- and 5-positions
of the benzene cycle [11, 15–17].
We previously found that copper tetra-4-(benzo-
triazol-1-yl)tetra-5-[4-(1-methyl-1-phenylethyl)phen-
oxy]phthalocyanine [18], which contains no bulky
peripheral aliphatic substituents, forms an enantio-
tropic mesophase and shows the ability to retain the
mesophase structure on glass transition [19]. There-
fore, for the research on the influence of the chemical
structure of substituted phthalocyanines on their physico-
chemical properties of interest is to vary the nature of
the substituents ortho to the 4-(1-methyl-1-phenyl-
ethyl)phenoxy group by prepacycle highly sym-
metrical phthalocyanines derived from 4-(1-methyl-1-
phenylethyl)phenol.
The aim of the present work was to synthesize octa-
4,5-[4-(1-methyl-1-phenylethyl)phenoxy]pthalocyanine
and its metal complexes and to study the influence of
the structure of the synthesized phthalocyanine deri-
vatives on their physicochemical properties.
First we synthesized 4,5-[4-(1-methyl-1-phenyl-
ethyl)phenoxy]phthalonitrile (2) starting from 4-bromo-
5-nitrophthalonitrile (1) (Scheme 1). The reaction was
1
For communication XIII, see [1].
2501

2502
ZNOIKO et al.
Scheme 1.
NO2
Br
NC
NC
1
6
O
4
O
K2CO3,
3
5
O
DMF
85−90oC
8 h
2
O
N
5
6
1
4
N
N
2
3
N
M
N
1
a, b
O
O
NC
NC
N
N
N
O
O
O
2
O
3a−3e
а, M(CH3COO)2·nH2O, 160–170°C; b, СoCl2·6H2O, 155–160°C; M = Mg (a, n = 4), Cu (b, n = 2), Co (c), Ni (d, n = 4),
Zn (e, n = 2).
1
performed in aqueous DMF at 80–90°С in the
presence of an equimolar amount of potassium carbo-
nate which acts as a deprotonating agent [20, 21], for
8 h. When the reaction time was decreased to 4 h, only
bromine substitution was observed, and no target
product formed.
The Н NMR spectrum of compound 2 displays an
upfield (2.19 ppm) 12-proton strong singlet signal of
the methyl groups of the 4-(1-methyl-1-phenylethyl)-
phenoxy substituents. Downfield benzene proton
signals of the phthalonitrile molecule (7.33 ppm) and
phenoxy (6.96–6.98 ppm) and oxyaryl groups (7.09–
7.17 ppm) are also observed.
The composition and structure of compound 2 were
confirmed by elemental analysis, MALDI‒TOF mass
spectrometry, 1Н NMR and IR spectroscopy. The mass
spectrum of compound 2 shows signals at m/z 549 and
588 corresponding to the [M + H]+ and [M + K]+ ions.
By melting compound 2 together with magnesium,
copper, nickel, and zinc acetates, as well as with cobalt
chloride for 1.5 h we synthesized the corresponding
octasubstituted metal phthalocyanines 3а–3d (Scheme 1).
Treatment of compound 3а with 5% aqueous HCl gave
phthalocyanine 4 (Scheme 2).
The IR spectrum of compound 2 does not contain
the stretching and deformation vibration bands of the
nitro group, which are present in the spectrum of the
starting 4-bromo-5-nitrophthalonitrile (1) [22], and
contains the stretching vibration bands of the cyano
(2233 cm–1) and Ar–O–Ar groups (1218 cm–1) [23].
The synthesized compounds are dark green solids
insoluble in water and readily soluble in chloroform,
acetone, and DMF. It should be noted that compounds
3а–3d are quite poorly soluble in conc. H2SO4.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 11 2016

NUCLEOPHILIC SUBSTITUTION IN 4-BROMO-5-NITROPHTHALONITRILE: XIV.
2503
Scheme 2.
O
O
O
O
O
O
O
O
N
N
N
N
NH
N
N
HCl (5%)
N
N
Mg
N
N
N
N
NH
N
N
O
O
O
O
O
O
O
O
3a
4
Phthalocyanine 4 does not dissolve in sulfuric acid
even on prolonged standing and decomposes on heating.
Since compounds 3а–3e and 4 contain 8 bulky 4-(1-
methyl-1-phenylethyl)phenoxy substituents that shield
the chelated metal atom (cobalt or copper) from от RF
radiation (like it was previously observed with other
phthalocyanine derivatives with bulky and long-chain
substituents [27, 28]) and enhance the solubility of the
As known [24, 25], the dissolution of phthalo-
cyanine and its derivatives in conc. H2SO4 is associated
with the protonation of the meso-nitrogen atoms of the
phthalocyanine macrocycle. Probably, in our case, the
bulky and branched 4-(1-methyl-1-phenylethyl)phenoxy
groups prevent efficient interaction of H2SO4 with the
macrocyclic core of the phthalocyanine molecule,
which is responsible for the low solubility of com-
pounds 3 and 4 in sulfuric acid.
1
compounds in chloroform, we could obtain the Н
NMR spectra of the synthesized copper, nickel, and
cobalt phthalocyanines to find that they are almost
completely coincide with the spectra of the parent
phthalonitrile 2.
The synthesized phthalocyanine derivatives were
identified by elemental analysis, IR and Н NMR
spectroscopy, and MALDI‒TOF mass spectrometry.
1
The electronic absorption (UV-Vis) spectra of octa-
substituted phthalocyanines 3 and 4 gave evidence
showing that the synthesized compounds all are
unassociated in organic solutions. Therefore, we could
measure their extinction coefficients (see table). A sol-
vatochromic effect that revealed itself in the
bathochromic shift of the Q-band by 3–8 nm for all the
studied compounds (Fig. 1), as well as in the increase
in the molar extinction coefficient in going from DMF
to chloroform, was observed. Furthermore, the position
of the longwave absorption band was affected by the
nature of the complexing metal, as evidenced by the
fact that the bathochromic shift of this band changes
with metal in the following order: 3c (Сo) < 3d (Ni) <
3a (Mg), 3b (Cu), 3e (Zn).
The IR spectra of octasubstituted phthalocyanines 3
and 4 display vibration bands of the oxyaryl groups
(1213–1216 cm–1), and well as skeletal vibration bands
(1320–1340, 1560–1605 cm–1) of the macrocylic core
of the phathalocyanine molecule [26]. At the same
time, the band at 2233 cm–1, characteristic of the cyano
groups [23] in phthalonitrile 2 is no longer observed,
which points to a lack of admixture of the parent
compound in the products. The spectrum of phthalo-
cyanine 4 shows bands at 3157 and 1016 cm–1 assignable
to endocyclic imino groups [26]. These bands are absent
from the spectrum of the parent magnesium phthalo-
cyanine 3а.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 11 2016

2504
ZNOIKO et al.
D
D
400
500
600
700
800
900
400
500
600
700
800
900
λ, nm
λ, nm
Fig. 2. Electronic absorption spectra of compounds 3а and
4 in different solvents (c = 0.85×10–5 M): (1) 3а (CHCl3);
(2) 4 (CHCl3); and (3) 4 (DMF).
Fig. 1. Electronic absorption spectra of compound 3c in (1)
DMF and (2) chloroform (c = 0.45×10–5 M).
UV-Vis spectrum of phthalocyanine 4 in chloro-
form contains two strong longwave bands, which is
characteristic of phthalocyanine ligands [24, 25]. In
DMF no splitting of the Q-band takes place (Fig. 2).
The lacking Q-band splitting in the basic medium is
explained by an increase in the symmetry of the
phthalocyanine molecule on the deprotonation of the
endocyclic nitrogen atoms in the organic base medium
to form the dianionic form of the phthalocyanine, which,
like metal phthalocyanines, has a D4h symmetry [29].
Comparison of the UV-Vis spectra of copper phthalo-
cyanine 3b and phthalocyanine 4 with those of the
previously studied tetra-4-(benzotriazol-1-yl)tetra-5-
[4-(1-methyl-1-phenylethyl)phenoxy]phthalocyanine
and its copper complex reveals hypsochromic shift of
Q-band by 4 nm on the replacement of the benzo-
triazole fragment by 4-(1-methyl-1-phenylethyl)phenoxy
group in organic solvents [18] and a bathochromic
shift of the longwave band by 28 nm for compound 3b
in conc. H2SO4 (Fig. 3).
The transition from organic solvents to conc. H2SO4
is accompanied by a bathochromic shift of the
longwave absorption bands by more than 100 nm (see
table, Fig. 3). This shift depends on the nature of the
complexing metal and increases in the order: 3а (Mg) <
3d (Ni) < 3e (Zn) < 3c (Co) < 3b (Cu). Compound 3а
in conc. H2SO4 decomposes even on short standing,
which is associated with demetalation and subsequent
decomposition of the macroheterocycle.
Thus, the nucleophilic substitution of the nitro
group and bromine by the 4-(1-methyl-1-phenyl-ethyl)-
phenoxy group was used to obtain 4,5-bis[4-(1-methyl-
1-phenylethyl)phenoxy]phthalonitrile. Melting the
latter compound together with some d-metal salts gave
previously unknown metal phthalocyanines. Demetala-
tion of the magnesium complex of octa-4,5-[4-(1-
methyl-1-phenylethyl)phenoxy]phthalocyanine gave
the corresponding phthalocyanine. The position of the
Electronic absorption spectra of octa-4,5-[4-(1-methyl-1-phenylethyl)phenoxy]phthalocyanines 3 and 4
ESP, λ, nm (log ε)
Comp. no.
М
DMF
CHCl3
H2SO4
3а
3b
3c
3d
3e
4
Mg
Cu
Co
Ni
361 (4.48), 613 (4.06), 679 (4.76)
344(4.92), 612 (4.71), 679 (5.15)
333(4.63), 600 (4.16), 665 (4.65)
371(4.41), 605 (4.34), 673 (4.84)
365 (4.85), 612 (4.75), 679 (5.00)
367 (4.44), 603(4.31), 678 (4.84)
383 (4.25), 618 (4.15), 685 (4.82)
340 (5.00), 615 (4.74), 684 (5.22)
326(4.72), 610 (4.27), 673 (4.82)
382 (4.39), 609 (4.33), 675 (4.95)
354 (4.74), 616 (4.34), 683 (5.08)
610 (4.32), 647 (4.33), 670 (4.86), 704 (4.88)
805
838
823
812
814
–
Zn
НН
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 11 2016

NUCLEOPHILIC SUBSTITUTION IN 4-BROMO-5-NITROPHTHALONITRILE: XIV.
Q-band is affected by the nature of the complexing
2505
D
metal, as evidenced by the bathochromic shifts.
EXPERIMENTAL
UV-Vis spectra were recorded in organic solvents
(DMF and chloroform), aqueous alkalis, and con-
centrated sulfuric acid on a HITACHI U-2001
spectrophotometer at room temperature in the range
325–900 nm. The IR spectra were registered on a
Nicolet Avatar 360 FTIR ESP spectrometer in the
range 400–4000 cm–1 in thin films (chloroform) and
KBr pellets. The 1Н NMR spectra (CDCl3) were
registered on a Bruker DRX-500 instrument. Elemental
analysis was performed on a FlashEA 1112 CHNS-O
analyzer. The MALDI‒TOF mass spectra were ob-
tained on a Shimadzu Biotech Axima Confidence
instrument in the positive ion mode, matrix 2,5-dihyd-
roxybenzoic acid.
λ, nm
Fig. 3. Electronic absorption spectra of compound 3b in
(1) DMF, (2) chloroform, (3) H2SO4, and (4) of copper tetra-
4-(benzotriazol-1-yl)tetra-5-[4-(1-methyl-1-phenylethyl)-
phenoxy]phthalocyanine in H2SO4 (с = 0.45×10–5 M).
4-Bromo-5-nitrophthalonitrile (1) was syn-
thesized by the known procedure [30], mp 140–142°С.
Found, %: C 38.10; Н 0.76; N 16.50. C8H2BrN3O2.
Calculated, %: C 38.16; Н 0.80; N 16.67.
Magnesium octa-4,5-[4-(1-methyl-1-phenylethyl)-
phenoxy]phthalocyanine (3а) was synthesized from
compound 2 and 21.4 mg of magnesium acetate tetra-
hydrate. Yield 37.2 mg (67%). IR spectrum, ν, cm–1:
2963, 2922, 2867 (СН3), 1567 (С–С), 1322, 1165
(СHAr), 1212 (Ar–O–Ar). Mass spectrum, m/z:
2219.29 (80.57) [M]+. М 2219.04. Found, %: С 82.05;
H 6.04; N 4.94. С152H128N8O8Mg. Calculated, %: С
82.27; H 5.81; N 5.05.
4,5-Bis[4-(1-methyl-1-phenylethyl)phenoxy]phthalo-
nitrile (2). A solution of 2.76 g (2 mmol) K2СО3 in
10 mL of water was added to a solution of 2.52 g
(1 mmol) of compound 1 and 4.24 g (2 mmol) of 4-(1-
methyl-1-phenylethyl)phenol in 70 mL of DMF. The
mixture was stirred at 80–90°С for 8 h and then poured
into water. The viscous reddish-brown liquid that
formed was separated, diluted with 10 mL of aqueous
isopropanol (1 :1, vol/vol), and left to stand for 3 days.
A precipitate formed and was filtered off, washed with
isopropanol and water, and dried in air at 80°С. Yield
2.40 g (44%), mp 123–125°С. IR spectrum, ν, cm–1:
2967, 2929, 2869 (СН3), 2233 (CN), 1589 (С–С),
Copper octa-4,5-[4-(1-methyl-1-phenylethyl)phen-
oxy] (3b) was synthesized from compound 2 and
21.7 mg of copper acetate dihydrate. Yield 43.8 mg
(80%). IR spectrum, ν, cm–1: 2966, 2929, 2872 (СН3),
1
1602 (С–С), 1272, 1137 (СHAr), 1214 (Ar–O–Ar). Н
NMR spectrum, δ, ppm: 7.31 s (8Н, Н1), 7.01–7.03 m
(16Н, Н2), 6.96–6.98 m (16Н, Н3), 7.07–7.22 m (40Н,
Н4–6), 2.17 s (48Н, СН3). Mass spectrum, m/z: 2257.57
(92.85) [M + 2Н]+. М 2255.91. Found, %: С 80.22; H
5.95; N 4.90. С152H128N8O8Cu. Calculated, %: С
80.84; H 5.71; N 4.96.
1
1318, 1162 (СHAr), 1217 (Ar–O–Ar). H NMR spec-
trum, δ, ppm: 7.33 s (2Н, Н1), 7.01–7.03 m (4Н, Н2),
6.96–6.98 m (4Н, Н3), 7.09–7.17 m (10Н, Н4–6), 2.19 s
(12Н, СН3). Mass spectrum, m/z 549.19 (34.95) [M +
Н]+, 588.13 (83.23) [M + K]+. М 548.68. Found, %: С
82.95; H 6.02; N 5.11. С38H32N2O2. Calculated, %: С
83.19; H 5.88; N 4.96.
Cobalt octa-4,5-[4-(1-methyl-1-phenylethyl)phen-
oxy]phthalocyanine (3c) was synthesized from com-
pound 2 and 23.8 mg of cobalt chloride hexahydrate.
Yield 42.5 mg (78%). IR spectrum, ν, cm–1: 2954,
2923, 2862 (СН3), 1561 (С–С), 1328, 1125 (СHAr),
Metal octa-4,5-[4-(1-methyl-1-phenylethyl)phen-
oxy]phthalocyanines 3а–3e. A thoroughly triturated
mixture of 55 mg (0.1 mmol) of compound 2, 50 mg
(0.8 mmol) of urea, and 0.1 mmol of metal acetate or
chloride was heated at 155–170°С for 1.5 h, after
which it was dissolved in chloroform and
chromatographed on alumina (eluent—chloroform).
1
1213 (Ar–O–Ar). Н NMR spectrum, δ, ppm: 7.33 s
(8Н, Н1), 7.00–7.03 m (16Н, Н2), 6.97–7.00 m (16Н,
Н3), 7.09–7.20 m (40Н, Н4–6), 2.17 s (48Н, СН3). Mass
spectrum, m/z: 2253.57 (92.83) [M + 2Н]+. М 2251.13.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 11 2016

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ZNOIKO et al.
Modifitsirovannye ftalotsianiny i ikh strukturnye analogi
(Modified Phthalocyanines and their Structural
Analogs), Moscow: URSS, 2012.
Found, %: С 80.82; H 6.00; N 4.82. С152H128N8O8Cо.
Calculated, %: С 81.01; H 5.72; N 4.97.
Nickel octa-4,5-[4-(1-methyl-1-phenylethyl)phen-
oxy]phthalocyanine (3d) was synthesized from
compound 2 and 24.8 mg of nickel acetate tetra-
hydrate. Yield 23.8 mg (43%). IR spectrum, ν, cm–1:
2960, 2920, 2863 (СН3), 1562 (С–С), 1321, 1125
3. Usol’tseva, N.V., Akopova, O.B., Bykova, V.V.,
Smirnova, A.I., and Pikin, S.A., Zhidkie kristally:
diskoticheskie mezogeny (Liquid Crystals: Discotic
Mesogens), Ivanovo: Ivanovsk. Gos. Univ., 2004.
4. Ince, M., Martínez-Díaz, M.V., Barberá, J., and Torres, T.,
J. Mater. Chem., 2011, vol. 21, p. 1531. doi 10.1039/
C0JM02420A
5. Erdoğan, B.S., Atilla, D., Gürek, A.G., and Ahsen, V.,
J. Porphyrins Phthalocyanines, 2014, vol. 18, no. 2,
p. 139. doi 10.1142/S1088424613501149
6. Atilla, D., Gürek, A.G., Basova, T.V., Kiselev, V.G.,
Hassan, A., Sheludyakova, L.A., and Ahsen, V., Dyes
Pigments, 2011, vol. 88, no. 3, p. 280. doi 10.1016/
j.dyepig.2010.07.007
1
(СHAr), 1214 (Ar–O–Ar). Н NMR spectrum, δ, ppm:
7.32 s (8Н, Н1), 7.01–7.03 m (16Н, Н2), 6.97–6.99 m
(16Н, Н3), 7.07–7.18 m (40Н, Н4–6), 2.19 s (48Н,
СН3). Mass spectrum, m/z: 2253.06 (90.12) [M]+. М
2253.43. Found, %: С 80.78; H 6.12; N 4.88.
С152H128N8O8Ni. Calculated, %: С 81.02; H 5.73; N 4.97.
Zinc octa-4,5-[4-(1-methyl-1-phenylethyl)phen-
oxy]phthalocyanine (3e) was synthesized from
compound 2 and 21.7 mg of zinc acetate dihydrate.
Yield 28.8 mg (53%). IR spectrum, ν, cm–1: 2965,
2933, 2869 (СН3), 1604 (С–С), 1270, 1131 (СHAr),
1213 (Ar–O–Ar). Mass spectrum, m/z: 2260.00 (92.75)
[M]+. М 2260.12. Found, %: С 80.48; H 6.05; N 4.87.
7. Quan Li and Lanfang Li., Thermotropic Liquid Crystals,
Ramamorthy, A., Ed., Dordrecht: Springer, 2007.
8. Uspekhi v izuchenii zhidkokristallicheskikh materialov
(Advances in Liquid Crystalline Materials), Usol’tse-
va, N.V., Ed., Ivanovo: Ivanovsk. Gos. Univ., 2007.
С
4.96.
152H128N8O8Zn. Calculated, %: С 80.78; H 5.71; N
9. Wohrle, D., Schnurpfeil, G., Makarov, S.G., Kazarin, A.,
and Suvorova, O.N., Macroheterocycles, 2012, vol. 5,
no. 3, p. 191. doi 10.6060/mhc2012.120990w
10. Deibel, C., Janssen, D., and Heremans, P., Org.
Electron., 2006, vol. 7, no. 6, p. 495. doi 10.1016/
j.orgel.2006.07.002
11. Lukyanets, E.A. and Nemykin, V.N., J. Porphyrins
Phthalocyanines, 2010, vol. 14, no. 1, p. 1. doi 10.1142/
S1088424610001799
Octa-4,5-[4-(1-methyl-1-phenylethyl)phenoxy]-
phthalocyanine (4) was prepared by adding 4 drops of
5% aqueous HCl to a solution of 10 mg of compound
3а in 2 mL of chloroform. The chloroform was then
removed, and the residue was washed with water to
neutral washings and dried in air at 70–80°С. Yield
8.2 mg (82%). IR spectrum, ν, cm–1: 3056 (NH), 2965,
2923, 2860 (СН3), 1565 (С–С), 1324, 1162 (СHAr),
1216 (Ar–O–Ar), 1016 (H2Pc). Mass spectrum, m/z:
2196.25 (80.57) [M]+. М 2196.75. Found, %: С 83.05;
H 6.10; N 5.00. С152H130N8O8. Calculated, %: С 83.11;
H 5.96; N 5.10.
12. The Porphyrin Handbook, Kadish, K.M., Smith, K.M.,
and Guilard, R., San Diego: Academic, 2003, vol. 16.
13. Jiang, Z., Ou, Z., Chen, N., Wang, J., Huang, J., Shao, J.,
and Kadish, K.M., J. Porphyrins Phthalocyanines,
2005, vol. 9, no. 4, p. 352. doi 10.1142/
S1088424605000447
14. Sekhosano, K.E., Amuhaya, E., Mack, J., and Niokong, T.,
J. Mater. Chem. C, 2014, vol. 2, p. 5431. doi 10.1039/
c4tc00505h
ACKNOWLEDGMENTS
The work was financially supported by the Ministry
of Education and Science of the Russian Federation in
the framework of the State Contract, on the equipment
of the Center for Collective Use, Ivanovo State
University of Chemical Technology.
15. Houdayer, A., Hinrichsen, P.F., and Belhadfa, A.,
J. Mater. Sci., 1988, vol. 23, p. 3854. doi 10.1007/
BF01106803
16. Sakamoto, K., Ohno-Okumura, E., Kato, T., and Soga, H.,
J. Porphyrins Phthalocyanines, 2010, vol. 14, no. 1,
p. 1. doi 10.1142/S1088424610001799
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