Synthesis of Magnesium Octa-4,5-phenoxyphthalocyanine and Sulfo- and Alkylsulfamoyl Derivatives on Its Basis

Article abstract of DOI:10.1134/S1070363218060178

By the reaction of nucleophilic substitution of bromine atom and the nitro group of 4-bromo-5- nitrophthalonitrile 4,5-diphenoxyphthalonitrile was obtained and on its basis new derivatives of octa-4,5- phenoxyphthalocyanine were synthesized soluble in wat

Full text of DOI:10.1134/S1070363218060178

ISSN 1070-3632, Russian Journal of General Chemistry, 2018, Vol. 88, No. 6, pp. 1148–1153. © Pleiades Publishing, Ltd., 2018.
Original Russian Text © S.А. Znoiko, A.I. Petlina, G.P. Shaposhnikov, N.N. Smirnov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 6,
pp. 968–973.
Synthesis of Magnesium Octa-4,5-phenoxyphthalocyanine
and Sulfo- and Alkylsulfamoyl Derivatives on Its Basis
S. А. Znoikoa*, A. I. Petlinaa, G. P. Shaposhnikova, and N. N. Smirnova
a Ivanovo State Chemical Technological University, Institute of Macroheterocyclic Compounds,
Sheremetevskii pr. 7, Ivanono, 153000 Russia
*e-mail: znoykosa@yandex.ru
Received December 14, 2017
Abstract—By the reaction of nucleophilic substitution of bromine atom and the nitro group of 4-bromo-5-
nitrophthalonitrile 4,5-diphenoxyphthalonitrile was obtained and on its basis new derivatives of octa-4,5-
phenoxyphthalocyanine were synthesized soluble in water- and organic solvents. The spectral properties and
thermodestruction of the products were investigated.
Keywords: 4-bromo-5-nitrophthalonitrile, octa-4,5-phenoxyphthalocyanine, phenoxy- and sulfophenoxysubstituted
phthalocyanines, Mg-phthalocyanine
DOI: 10.1134/S1070363218060178
Phthalocyanines, whose key structural motif is
porphyrin chromophore modified with aza-bridges [1],
remain the objects of constant intense studies [1–3].
Particular interest attract aryloxy substituted phthalo-
cyanines [4–6] as well as their water-soluble deriva-
tives, as new materials for nanotechnology [7–9].
properties of organic compounds are very sensitive to
homogeneity of the studied compound [16, 17]. Hence,
to avoid the formation of a mixture of randomers, it is
better to prepare highly symmetrical derivatives, that
is, octaphenoxysubstituted phthalocyanines [18–21],
which also possess a number of useful properties.
However, there are no data in the literature on sulfonic
acids and sulfonamides of octaphenoxysubstituted
phthalocyanines, so it was of interest to synthesize new
water- and organosoluble derivatives of octaphenoxy
substituted phthalocyanines.
Phenoxy group is the simplest aroxy substituent. At
the same time the phenoxy and sulfophenoxy
substituted phthalocyanines possess a number of useful
properties. Thus, water-soluble metal complex of tetra-
4-(4-sulfophenoxy)phthalocyanine with cobalt(II)
exhibits an activity in oxidation of mercaptans in the
process of catalytic purification of liquified casing-
head gas, and its activity is higher than that of
commercial catalyst, cobalt disulfophthalocyanine, and
the degree of conversion, by an example of propane-
thiol, is higher [10]. The metal complex with zinc(II)
of similar structure demonstrated luminescent proper-
ties with the quantum yield of luminescence and the
yield of singlet oxygen being one of the best among
the investigated compounds [11]; it also shows
antimicotic and antiviral activity [12].
With the aforesaid in mind, the goal of the present
work was the synthesis and investigation of some
physicochemical properties of sulfo and alkylsulfa-
moyl derivatives of octa-4,5-phenoxyphthalocyanine.
In the first stage the initial 4,5-diphenoxyphthalonitrile
was synthesized (Scheme 1).
The method is known of the synthesis of 4,5-di-
phenoxyphthalonitrile 3 from 4,5-dichlorophthalonitrile
in nonaqueous DMSO with addition by portions of
potassium carbonate [22–24]. The reaction time did
not exceed 2 h, the yield of product 3 reached 82%.
The replacement of DMSO by DMF and the increase
in the time of heating did not increase the yield.
Since tetrasubstituted phthalocyanines are prepared
on the basis of the corresponding unsymmetrically
substituted phthalonitriles, the formation of inseparable
mixtures of positional structural isomers is possible
[2, 13–15]. It is noteworthy that physicochemical
There was also an attempt to synthesize compound
3 basing on 4-bromo-5-nitrophthalonitrile 1 in aqueous
DMF in the presence of potassium carbonate as
1148

SYNTHESIS OF MAGNESIUM OCTA-4,5-PHENOXYPHTHALOCYANINE
1149
Scheme 1.
HO
HO
DMF_H2O, K2CO3,
80_90°C, 8 h
DMF_H2O, K2CO3,
NC
NC
O
20_25°C, 0.5 h
NO2
2
HO
DMF_H2O, K2CO3, 80_90°C, 8 h
NC
NC
Br
NC
NC
O
NO2
O
3
1
HO
DMF, K2CO3, 80_90°C, 8 h
NC
NC
Br
NO2
deprotonating agent [25] with the isolation of the
intermediate nitrosubstituted phthalonitrile 2. This led
to an increase in the reaction time, complicated the
synthetic procedure, and decreased the yield of the
target product to 78%. In simultaneous substitution of
bromine and nitro group in aqueous DMF in the
presence of potassium carbonate at 80–90°С in the
course of 8 h (Scheme 1) compound 3 is formed in a
higher yield (85%). Therefore, the use of 4-bromo-5-
nitrophthalonitrile as a precursor allows preparing 4,5-
diphenoxyphthalonitrile 3 in a higher yield than when
using commercial 4,5-dichlorophthalonitrile.
group in the ortho-positions to oxygen at 7.67 ppm and
to the sulfochloride group at 8.29 ppm, and the signal
of protons of the benzene rings of the phthalocyanine
molecule at 7.63 ppm. Sulfonic acid 6 was synthesized
by hydrolysis of sulfochloride 5 in boiling water. In
the 1Н NMR spectrum of sulfonic acid 6 the signals are
broader as compared to those in the spectrum of
sulfochloride 5, the signal of SO3H groups appears at
8.94 ppm, and a slight shift was observed for the signal
of proton in the position 3 of the phenoxy group.
Alkylsulfamoyl derivatives of phthalocyanines 7, 8
were obtained by the reaction of sulfochloride 5 with
diethyl- and octadecylamine in boiling acetone
(Scheme 2).
Then, based on compound 3, magnesium octa-4,5-
phenoxyphthalocyanine 4 was obtained by the nitrile
method in the presence of magnesium acetate by
heating for 2 h at 180–185°С (Scheme 2).
The analysis of electron absorption spectra (UV-
Vis specta) of octaphenoxy substituted phthalocyanines
in DMF revealed that the introduction of substituents
in the para-position of the phenoxy groups results in a
small red shift of the longwave absorption band, the
shift being the larger the bulkier and/or longer is the
introduced substituent (Table 1).
Compound 4 was extracted from the reaction
mixture with chloroform and purified by column
chromatography with chloroform as an eluent with
subsequent removal of the solvent. The synthesized com-
pound is dark-green solid insoluble in water, readily
soluble in organic solvents: chloroform, acetone, and
DMF.
The spectrum of magnesium octa-4,5-phenoxy-
phthalocyanine 4, originally containing a single Q
band, suffers notable changes after sulfochlorination
and subsequent hydrolysis. Due to high lability of
magnesium complexes of phthalocyanine in acid
media, not only the sulfonic group is introduced but
Magnesium phthalocyanine 4 was treated with
excess of chlorosulfonic acid and thionyl chloride to
obtain sulfochloride 5. The 1Н NMR spectrum of com-
pound 5 contains the signals of protons of the phenoxy
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 6 2018

1150
ZNOIKO et al.
Scheme 2.
SO2Cl
SO2Cl
O
O
O
O
ClO2S
SO2Cl
HSO3Cl,
N
N
N
SO2Cl,
25°C,
0.5 h
N
N
Mg
N
N
N
O
O
O
O
O
O
O
O
Mg(OAc)2 4H2O
180_185°C, 2 h
N
HN
N
NH
3
N
N
N
N
SO2Cl
SO2Cl
O
O
ClO2S
O
O
SO2Cl
4
5
(CH3)2C=O,
H2O, 100°C
HХ, 60_70°C
SO3H
SO3H
O
O
SO2Х
SO2Х
HO3S
SO3H
O
ХO2S
SO2Х
O
N
HN
N
N
N
N
N
N
N
N
O
O
O
O
O
O
O
O
NH
HN
NH
N
N
N
SO3H
SO3H
SO3H
SO2Х
ХO2S
SO2Х
SO2Х
HO3S
O
O
O
O
7, 8
6
X = N(Et)2 (7), NHC18H37 (8).
also the metal atom is removed, as proved by the
presence of two longwave absorption bands in the UV-
Vis specta of compounds 6–8 (Table 1).
Sulfonic acid 6 is soluble in water and aqueous
alkaline media. UV-Vis specta of this compound in
water is characterized by the presence of broadened
Table 1. Electron absorption spectra of octaphenoxysubstituted
Table 2. Temperature parameters of thermooxidative destruction
phthalocyanines
of octaphenoxy substituted phthalocyanines
T
exo/endo, °С
II stage
Comp.
no.
λmax, nm
ΔTexo, °С
Comp.
I stage
no.
DMF
CHCl3
H2SO4
4
6
7
8
290
264а
260а
326
570
492
571
484
500–650
475–540
475–620
480–600
4
6
7
8
678
683
–
–
669, 696
648, 698
668, 701
767, 804
770, 804
813, 874
664, 700
663, 701
a Temperature at which the weight loss is maximal.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 6 2018

SYNTHESIS OF MAGNESIUM OCTA-4,5-PHENOXYPHTHALOCYANINE
1151
Q bands at 670 and 701 nm as well as by intense
diffuse absorption band at 640 nm. The shape of the
spectrum suggests that compound 6 exists in water in
an associated form [26].
4-bromo-5-nitrophthalonitrile. Fusion of this compound
with magnesium acetate gave magnesium octa-4,5-
phenoxyphthalocyanine, and on its basis new water-
and organosoluble derivatives of octa-4,5-phenoxy-
phthalocyanine were synthesized. It was found that
introduction of alkylsulfamoyl fragments causes a red
shift of the longwave absorption band of the syn-
thesized compounds. Thermogravimetric study has
shown that the highest temperature of the maximum
exo effect was observed for magnesium octa-4,5-
phenoxyphthalocyanine and for the synthesized on its
basis octa-4,5-(4-diethylsulfamoylphenoxy)phthalocyanine.
The lowest temperature of the maximum exo effect
was observed for para-octadecylsulfamoylphenoxy-
substituted phthalocyanine.
UV-Vis specta of the synthesized compounds in
conc. sulfuric acid are characterized by a red shift of the
Q band with respect to the spectra in organic solvents
(Table 1) by more than 100 nm. In the case of compound
8, an additional intense absorption band appears in the
long-wave region of the spectrum at 874 nm; the same
band was fixed in the spectra of 6, 7 but only as an
inflection.
Note the poor solubility of all synthesized com-
pounds in sulfuric acid, connected, apparently, with the
presence of eight bulky phenoxy groups on the peri-
phery of the phthalocyanine molecule that, in addition,
contain branched alkyl substituents (in the case of
compounds 6–8) [26], which hinder protonation of the
meso-nitrogen atoms of the phthalocyanine macroring.
Phthalocyanine derivatives containing long and/or
branched alkyl fragments on the periphery of the
molecule are known to be of interest from the view-
point of manifesting liquid crystal properties [27–29].
Therefore, we have studied the behavior of compounds
4, 6–8 at heating in the presence of air oxygen (Table 2).
The effect of the nature of the substituents in the
para-position of the phenoxy group on the behavior of
the synthesized compounds at heating was found
(Table 2). It was noted, that the process of thermo-
destruction of sulfo (6) or diethylsulfamoyl derivatives
(7) in the first stage is followed by intense loss of the
mass of the studied sample approximately by 55–60%.
Therewith, on the differential scanning calorimetry
(DSC) curve an intense endo peak was fixed at 260–
264°С. The temperature of maximal exo effect for the
sulfoderivative 6 is by 79°С lower than that of the
starting phthalocyanine 4. The presence of bulky
diethylsulfamoyl fragments in the molecule of phthalo-
cyanine 7 causes the increase in the temperature of
maximal exo effect to 570°С (Table 2).
EXPERIMENTAL
Electron absorption spectra were recorded in
organic solvents (DMF and chloroform), aqueous
alkali media, and concentrated sulfuric acid on a
HITACHI U-2001 spectrometer at room temperature
in the range 325–900 nm. IR spectra were taken on an
Avatar 360 FT-IR ESP instrument in the range 400–
4000 cm–1 from KBr pellets. MALDI-TOF mass
spectra were obtained on a Shimadzu Biotech Axima
Confidence mass spectrometer in the positive ions
mode. As a matrix, 2,5-dihydroxybenzoic acid was used.
Thermooxidative destruction of the synthesized
phthalonitriles was studied on a STA 449 F3 Jupiter
(Netzsch, Germany) instrument for synchronous
thermal analysis in oxygen–argon atmosphere in
platinum crucible, heating rate 5°С/min. Prior to
carrying out the elemental and thermogravimetric
analysis the samples of the studied compounds were
heated at 110°С for 2 h.
4-Bromo-5-nitrophthalonitrile (1) was syn-
thesized by the known procedure [30], mp 140–142°С.
Mass spectrum, m/z 251.18 [M – H]+; calculated
252.03. Found, %: C 38.10, Н 0.76, N 16.50.
C8H2BrN3O2. Calculated, %: C 38.16, Н 0.80, N 16.67.
4-Nitro-5-phenoxyphthalonitrile (2). 0.25
g
The process of decomposition of octadecylsulfa-
moyl derivative 8 proceeds also in two steps, the
temperature of maximal exo effect of compound 8
being by 86°С lower than that of the initial magnesium
octa-4,5-phenoxyphthalocyanine 4.
Therefore, in the present work, 4,5-diphenoxy-
phthalonitrile was synthesized by nucleophilic substitu-
tion of the bromine atom and the nitro group of
(1 mmol) of 4-bromo-5-nitrophthalonitrile and 0.091 g
(1 mmol) of phenol preliminarily crystallized from
hexane were dissolved in 50 mL of DMF, and the
solution of 0.14 g (1 mmol) of potassium carbonate in
5 mL of water was added. The reaction mixture was
stirred at 20–25°С for 0.5 h, then the target product
was filtered off, washed with hot water till the smell of
phenol ceased, and dried at 80–90°С. Yield 0.24 g
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 6 2018

1152
ZNOIKO et al.
(94%). IR spectrum, ν, cm–1: 2234 (C≡N), 1535
[νas(NO2)], 1345 [νs(NO2)], 1208 (ArOAr). Found, %:
C 63.57, H 2.58, N 18.03. C14H7N3O3. Calculated, %:
C 63.40, H 2.66, N 18.10.
sulfonic acid and 2 mL (18 mmol) of thionyl chloride
0.25 g (0.2 mmol) of compound 4 was added at
vigorous stirring. The reaction mixture was stirred at
20°С in the course of 0.5–1 h, then poured on ice
treated with sodium chloride. The precipitate was
separated using glass frit filter and dried in desiccator
over sulfuric acid during 3 days. The target compounds
were extracted with acetone, the solvent removed to
obtain dark-green solid compound, readily soluble in
acetone and DMF, moderately soluble in chloroform.
Yield 0.33 g (80%). IR spectrum, ν, cm–1: 3563 (ОН),
1614 (С–С), 1530 (N=), 1322 (S=O), 1291 (СAr-H),
4,5-Diphenoxyphthalonitrile (3). a. 0.30
g
(1.5 mmol) of 4,5-dichlorophthalonitrile and 0.28 g
(3.0 mmol) of phenol preliminarily crystallized from
hexane were dissolved in 15 mL of DMF and a
solution of 0.42 g (3 mmol) of potassium carbonate in
1 mL water was added. The reaction mixture was
stirred at 80–90°С for 12 h, then the target product was
filtered off, washed with hot water till the smell of
phenol ceased, and dried at 80–90°С. Yield 0.26 g
(82%). Found, %: C 76.38; H 3.98; N 8.72. C20H12N2О2.
Calculated, %: C 76.91; H 3.87; N 8.97.
1
1224 (ArOAr), 714 [δ(С–Н). Н NMR spectrum, δ,
ppm (CDCl3): 8.29 d (16Н, Н3, Jнн = 8.15 Hz), 7.67 d
(16Н, Н2, Jнн = 8.17 Hz), 7.63 s (16Н, Н1).
Octa-4,5-(4-sulfophenoxy)phthalocyanine
(6).
b. Compound 3 was prepared similarly from 0.26 g
(1 mmol) of 4-nitro-5-phenoxyphthalonitrile, 0.096 g
(1 mmol) of phenol and 0.14 g (0.1 mmol) of
potassium carbonate; reaction time 9 h. The target
product was filtered off, washed with 2-propanol, and
dried at 80–90°С. Yield 0.21 g (78%). IR spectrum, ν,
cm–1: 2226 (CN), 1588 (С-Сskel), 1561 (–N=), 1243
(ArOAr), 693 (С-Нdef). Found, %: C 76.42; H 4.00; N
8.69. C20H12N2О2. Calculated, %: C 76.91; H 3.87; N 8.97.
Mixture of 204 mg (0.1 mmol) of compound 5 and
10 mL of water was heated to complete dissolution,
then water was removed. The obtained sulfonic acid
was purified by column chromatography on silica M60
eluting with water. Yield 126 mg (67%). IR spectrum,
ν, cm–1: 3407 (ОН), 1587 (С–С), 1532 (N=), 1279
(СAr–H), 1240 (ArOAr), 1166 (S=O), 689 [δ(С–Н)].
1Н NMR spectrum (DMSO-d6), δ, ppm: 9.84 s (8Н,
SO3H), 8.35 s (16Н, Н3), 7.75 m (16Н, Н1), 7.65 m
(16Н, Н2). Found, %: C 49.75; H 3.08, N 5.77; S
12.89. C80H50N8О32S8. Calculated, %: C 50.79; H 2.66;
N 5.92; S 13.56.
c. Compound 3 was prepared similarly from 2.52 g
(0.01 mol) of 4-bromo-5-nitrophthalonitrile, 1.82 g
(0.02 mol) of phenol and 2.76 g (0.02 mol) of
potassium carbonate; reaction time 9 h. in 7 mL water.
The target product was filtered off, washed with hot
water until the smell of phenol ceased, and dried at 80-
90°С. Yield 2.65 g (85%). IR spectrum, ν, cm–1: 2227
(CN), 1589 (С-Сskel), 1282 (СAr-H), 1243 (ArOAr).
Mass spectrum, m/z: 313 [M + H]+ (33%), 335 [M +
Na]+ (97%), 350 [M + K]+ (50%); calculated 312.
Found, %: C 76.55; H 4.10; N 8.78. C20H12N2О2.
Calculated, %: C 76.91; H 3.87; N 8.97.
Octa-4,5-(4-alkylsulfamoylphenoxy)phthalo-
cyanines (7, 8). To a solution of 204 mg (0.1 mmol) of
compound 5 in 30 mL of acetone the excess of
diethylamine or 0.22 g of octadecylamine was added.
The mixture was refluxed at 60°С for 1–1.5 h. The
process was monitored by the completeness of dissolu-
tion of a sample of the reaction mixture in chloroform.
After completion of the reaction, acetone was removed,
the target products were extracted from the reaction
mixture with chloroform. Finally, the products were
purified by column chromatography on silica M60
eluting with chloroform.
Magnesium octa-4,5-(phenoxy)phthalocyanine (4).
A mixture of 0.31 g (0.1 mmol) of compound 3 and
0.11 g (0.05 mmol) of magnesium acetate tetrahydrate
was heated for 2 h at 180–185°С, then cooled and
dissolved in chloroform. The precipitate was filtered
off, the residue evaporated and chromatographed on
silica using toluene as an eluent. Yield 0.27 g (82%).
Mass spectrum, m/z: 1273 [M]+, calculated 1273.
Found, %: C 75.20; H 4.01; N 8.55. C80H48MgN8О8.
Calculated, %: C 75.45; H 3.80; N 8.80.
Compound 7. Yield 193 mg (83%). IR spectrum,
ν, cm–1: 3424 (ОН), 3071 (NH), 2975, 2821 (CH2,
CH3), 1575 (С–С), 1540 (N=), 1387 [δ(NH)], 1276
(СAr–H), 1240 (ArOAr), 1131 (S=O). Found, %: C
56.82; H 6.02, N 9.44; S 10.60. C112H122N16О24S8.
Calculated, %: C 57.67; H 5.27; N 9.61; S 10.99.
Compound 8. Yield 280 mg (72%). IR spectrum,
ν, cm–1: 3421 (ОН), 2921, 2843 (CH2, CH3), 1590
(С–С), 1532 (N=), 1340 [δ(NH)], 1270 (СAr–H), 1240
Octa-4,5-(phenoxy)phthalocyanine sulfochloride
(5). To the mixture of 2 mL (18 mmol) of chloro-
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SYNTHESIS OF MAGNESIUM OCTA-4,5-PHENOXYPHTHALOCYANINE
1153
13. Deibel, C., Janssen, D., and Heremans, P., Org.
Electronics, 2006, vol. 7, no. 6, p. 495. doi 10.1016/
j.orgel.2006.07.002
(ArOAr), 1131 (S=O), 679 [δ(С–Н)]. Found, %: C
68.27; H 9.35, N 5.33; S 6.81. C224H346N16О24S8.
Calculated, %: C 68.92; H 8.93; N 5.74; S 6.57.
14. Lukyanets, E.A. and Nemykin, V.N., J. Porph.
Phthalocyan., 2010, vol. 14, no. 1, p. 1. doi 10.1142/
S1088424610001799
ACKNOWLEDGMENTS
15. Jiang, Z., Ou, Z., Chen, N., Wang, J., Huang, J., Shao, J.,
and Kadish, K.M., J. Porph. Phthalocyan., 2005, vol. 9,
no. 4, p. 352. doi 10.1142/S1088424605000447
16. Houdayer, A., Hinrichsen, P.F., and Belhadfa, A., J. Mater.
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17. Moskvin, D.O., Sotsky, V.V., Kudayarova, T.V.,
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Acta Phys. Polonica (A), 2015, vol. 127, no. 4, p. 950.
doi 10.12693/APhysPolA.127.950
This work was performed with the support from the
State Contract of the Ministry of Education and
Science of the Russian Federation, Agreement no.
4.1929.2017/4.6 using the equipment of the Center for
Joint Use of ISUCT.
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