Erbium and ytterbium complexes with the phtalocyanines with aryloxy and chlorine substituents

Article abstract of DOI:10.1134/S1070363209080258

By nucleophilic substitution of chlorine atoms in tetrachlorophthalonitrile by phenoxy- or 1-naphthyloxy groups aryloxychlorophthalonitriles were synthesized and on this basis respective substituted erbium and ytterbium phthalocyanines with chloro-, aceta

Full text of DOI:10.1134/S1070363209080258

ISSN 1070-3632, Russian Journal of General Chemistry, 2009, Vol. 79, No. 8, pp. 1728–1734. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © V.P. Kulinich, T.A. Lebedeva, A.V. Borisov, V.N. Gorelov, G.P. Shaposhnikov, 2009, published in Zhurnal Obshchei Khimii, 2009,
Vol. 79, No. 8, pp. 1369–1375.
Erbium and Ytterbium Complexes with the Phtalocyanines
with Aryloxy and Chlorine Substituents
V. P. Kulinich, T. A. Lebedeva, A. V. Borisov, V. N. Gorelov, and G. P. Shaposhnikov
Ivanovo State Chemical Technological University
pr. Engelsa 7, Ivanovo, 153460, Russia
e-mail: ttoc@isuct.ru
Received December 30, 2008
Abstract—By nucleophilic substitution of chlorine atoms in tetrachlorophthalonitrile by phenoxy- or 1-
naphthyloxy groups aryloxychlorophthalonitriles were synthesized and on this basis respective substituted
erbium and ytterbium phthalocyanines with chloro- , acetate- or acetylacetonate anions as extra ligands. The
compounds obtained were characterized by elemental analysis, chromato-mass spectrometry, IR, 13С NMR,
and electronic spectroscopy.
DOI: 10.1134/S1070363209080258
Bifunctional substituted phthalocyanines are
interesting for the study of combined influence of the
groups of different nature on their properties and in
practical aspect as compound in which useful features
owing to introduction of such substituents are
combined.
Cl
Cl
Cl
Cl
CN
CN
ArO
ArO
CN
CN
ArOH
Cl
Cl
IIа, IIb
I
Continuing our research in this direction [1], we
present in this communication the data on the synthesis
and study of lanthanide (erbium and ytterbium)
complexes with aryloxychloro-substituted phthalo-
cyanines. The choice of such combination of
substituents is defined by the data that the introduction
of chlorine to the benzene ring of phthalocyanine
ligand increases thermal and light stability and other
useful properties [2, 3]. Aryloxy groups, in turn, due to
weakening the intermolecular interaction promote
increase in solubility in low polar organic solvents that
permits the application of chromatographic methods of
purification and extends the areas of investigation and
practical application.
(а);
Ar =
(b).
Nph
Ph
by reaction of tetrachlorophthalonitrile (I) with aromatic
hydroxy compounds, phenol (PhOH) or 1-naphthol
(NphOH).
Analysis of our experimental data obtained those
and published [4] on the substitution of chlorine in the
nitrile I by О-nucleophiles led us to conclusion that at
any stoichiometric ratio of the reagents always formed
more than of one product: a mixture is formed of
compounds with different ratios and positions of
chlorine and aryloxy groups. By varying conditions of
the synthesis it is possible to predominate formation of
either mono-, or di- or triaryloxy substituted chloro-
phthalonitriles. Reaction of nitrile I with ArОH, in
contrast to the reaction with S-nucleophiles [5], does
not lead to the substitution of all four chlorine atoms.
As noted in [4], attempted complete substitution of
For the preparation of substituted phthalocyanines
often is used template synthesis is often used on the
respec-tive derivatives of phthalic acid, in particular,
of phthalo-nitriles [1]. Therewith it becomes possible to
isolate phthalocyanines with a certain number and
certain positions of substituents. Proceeding from this
fact, we included in the first step of this work the
preparation of 4,5-diaryloxy-3,6-dichlorophthalonitriles
1728

ERBIUM AND YTTERBIUM COMPLEXES WITH THE PHTALOCYANINES
1729
chlorine atoms by phenoxy groups in DMF medium at
elevated temperature failed. Under these conditions
formed impurifiess of brown tarry substances con-
taminating the obtained phenoxychloro substituted nitriles.
T
Among the aryloxychloro substituted phthalo-
nitriles the most interesting for us are 4,5-disubstituted
compounds because their application to the synthesis
of the respective hexa-substituted phthalocyanine the
formation of randomers is excluded.
2500
2000
1500
1000
500
For the synthesis of 4,5-diaryloxy-3,6-dichloro-
phthalonitriles (IIa, IIb) we reacted tetrachloro-
phthalonitrile (I) with aromatic hydroxy compounds
(ArOH) in the presence of lithium hydroxide in the
medium of dimethyl sulfoxide at room temperature [6].
This method allows obtaining nitriles IIa, IIb with
higher yield (70–73%) as compared with that
described in [4] (45%). After completing the reaction,
the reaction mixture was poured to water–ice mixture,
the precipitate formed was separated, washed with
aqueous NaOH and then with water to neutral. The
completeness of removing the unreacted ArOH was
shown by a negative reaction with a diazo compound.
The precipitate was dried in a vacuum and recrystal-
lized from acetone. Final purification was carried out
by column chromatography on aluminum oxide with
benzene–ethanol mixture as eluent. At the eluting,
initially was separated a zone containing triaryloxy-
chlorophthalonitrile admixtures and then the zone of the
target nitriles IIа and IIb. The admixtures of aryloxy-
trichlorophthalonitriles remains at the start. Thus, the
difference in chromato-graphic mobility of aryloxychloro-
phthalonitriles differ by the ratio of substituents allowed
us to separate phthalonitriles IIa and IIb that were
then identified by the elemental analysis, chromato-
mass-spectrometry, IR and 13С NMR spectroscopy.
Wave number, cm–1
Fig. 1. IR spectrum of compound IIb.
vibrations (750–760 cm–1) and absorption at 1209–
1225 cm–1 corresponding to Ar–O–Ar vibrations.
In addition, unlike tetrachlorophthalodinitrile
whose spectrum contains a band of C–Cl stretching
vibrations (750–766 cm–1), in the spectra of IIa, IIb
appears absorption at 1209–1225 cm–1 corresponding
to Ar–O–Ar vibrations [7].
In the 13С NMR spectrum of nitrile IIa a group of
carbon signals is registered which by comparison with
the theoretically calculated spectrum and with
accounting for the published data [4, 8] should be
assigned as follows: 134.5 ppm to chloro-substituted,
152.1 ppm to phenoxy-substituted, 116.4 ppm to cyano
substituted carbon atoms of benzene ring. A signal at
113.5 ppm corresponds to the carbon atom of cyano
group, at 155.1 ppm, to carbon atoms of phenyl ring.
The fact that the 13С NMR spectrum of nitrile IIa
contain less number of signals compared to the spec-
trum of 3,5-diphenoxy-4,6-dichloro-substituted phthalo-
nitrile [4] confirms substitution of chlorine atoms in
tetra-chlorophthalonitrile at the positions 4 and 5.
Thus, the scope of the methods of investigations, in
particular, elemental analysis, chromato-mass spectro-
metry, IR and 13С NMR spectroscopy, confirms the
structure of the synthesized phthalonitriles IIa, IIb, in
particular, the number and positions of substituents on
benzene ring.
In the chromatograms of the isolated nitriles IIа
and IIb were registered only single peaks. The mass-
spectrum of IIa has a peak at m/z = 381 corresponding
to the main molecular ion of dichlorodiphenoxy-
phthalonitrile as well as several peaks of low intensity
corresponding to its fragmentation products, of whose
significant are ions with m/z = 346, 311 and 253
corresponding to the diphenoxychloro-, diphenoxy-
and chlorophenoxyphthalonitrile ions.
Starting with diaryloxydichlorophthalonitriles IIa,
IIb we synthesized along the scheme below a series of
erbium and ytterbium complexes IIIa, IIIb, VIa–
VIIIa, VIb–VIIIb.
In the IR spectra of nitriles IIa, IIb (Fig. 1) appears
a characteristic band of С≡N bond stretching vibra-
tions. Unlike unsubstituted phthalonitrile, in the spec-
tra of IIa, IIb is ibserved a band of C–Cl stretching
Initially, the reaction was carried out at heating of
nitriles IIa, IIb with erbium at ytterbium salts (chlo-
rides, acetates or acetylacetonates). Formation of
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1730
KULINICH et al.
OAr
Cl
ArO
Cl
Cl
Cl
Cl
Cl
N
N
N
Er
N
ArO
ArO
OAr
OAr
ErCl3
N
IIа, IIb
N
N
Cl
N
Cl
Cl
Mg(AcO)2
ArO
IIIа, IIIb
OAr
ClErPc(ArO)8Cl8
Ar = Ph (IIIа)
Ar = Nph (IIIb)
+ 2 H+
ML6
MgPc(ArO)8Cl8
H2Pc(ArO)8Cl8
LMPc(ArO)8Cl8
−2 Mg2+
IVа, IVb
Vа, Vb
VIа, VIb−VIIIа, VIIIb
M = Er; L = AcO (VIа, VIb)
M = Yb; L = AcO (VIIа, VIIb)
L = Acac (VIIIа, VIIIb)
CH3
O
O
H3C
.
CH C
,
(a),
C
Ar =
(b); L = H3C C
AcO
−O
O
Nph
Ph
Acac
complexes occurred at the temperature 230–240°С,
that is, by 20–30°С higher than the used at the
preparation of the complexes of copper, cobalt and
other bivalent metals [4, 9]. By this method we
succeeded in the synthesis with retaining the extra
ligand the metal chloride phthalocyanine complexes
IIIa, IIIb only. For the acetate and acetylacetonate
complexes VI–VIII we applied reaction of initially
prepared compounds Va, Vb containing no metal with
erbium and ytterbium acetates and acetylacetonates in
the medium of aprotic solvent DMF.
carried out by heating in acetic acid, from complex
IVb, by heating in a mixture of acetic acid and
pyridine. Monitoring of the processes of formation of
complexes IIIa, IIIb, IVa, IVb obtained by nitrilic
method, demetallation of complexes IVa and IVb and
further metallation of Va, Vb with the erbium and
ytterbium salts was carried out by monitoring of
electron absorption spectra (Figs. 2, 3), whose analysis
will be given below.
The synthesized phthalocyanines were purified
using various methods. The metal chloride and acetate
excess was removed by washing with water. As noted
above, the presence on benzene rings of III–VIII of
bulky aryloxy groups provides good solubility in low
polar organic solvents (benzene, chloroform, acetone
etc). This allowed to isolate them by extraction from
For the synthesis of phthalocyanines Va, Vb
containing no metal, we initially synthesized the
complexes of magnesium IVa, IVb by reaction of
nitriles IIa, IIb with magnesium acetate [Mg(OAc)2·
4H2O]. Removal of the metal from complex IVa was
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ERBIUM AND YTTERBIUM COMPLEXES WITH THE PHTALOCYANINES
1731
(a)
(a)
D
D
400 500 600 700 800 900 λ, nm
400 500 600 700 800 900 λ, nm
(b)
(b)
D
D
400 500 600 700 800 900 λ, nm
400 500 600 700 800 900 λ, nm
Fig. 2. Electron absorption spectra (benzene solutions):
(a) IVа and (b) VIa.
Fig. 3. Electron absorption spectra (benzene solutions):
(a) VIа and (b) VIb.
the reaction mixture and apply chromatographic
method for purification. As a sorbent was used alumi-
num oxide, as eluent a mixture of benzene and ethanol.
We observed that their solubility varies depending on
the extra ligand (L) and grows in the series chloride–
acetate–acetylacetonate complexes.
Structures of the synthesized complexes are
confirmed with accounting for the structure of the
parent phthalonitriles and the data of elemental
analysis, IR and electron spectroscopy.
For the preparation of complexes (III, VI–VIII), as
the initial phtalocyanogenes nitriles IIa, IIb were taken
without purification. This allowed to avoid nitrile loss
at chromatographic purification and thus to enhance
phthalocyanine yield by 10–15 %. Further, like the
case of chromatographic purification of nitriles, using
the difference in sorption ability of the phthalo-
cyanines with various ratio of chlorine and aryloxy
substituents and dissimilar in positions of Q-bands in
their electronic spectra we separated these compounds
by chromatography. In the process of purification first
eluted the admixtures of tetra(triaryloxychloro)-sub-
stituted phthalocyanines, then followes the zone of tetra
(diaryloxy-dichloro)phthalocyanine. Admixtures of
tetra(aryloxy-trichloro)- and tetrachlorophthalocyanines
remain at the start.
At the analysis of IR spectra it was observed that
the bands of stretching vibrations of bonds Ar–Cl
(750–760 cm–1) and Ar'–O–Ar (~1209–1225 cm–1)
noted for parent phthalonitriles IIa, IIb remain in the
spectra of the substituted phthalocyanines. The
presence of acetate and acetylacetonate extra-ligand in
complexes VI–VIII was confirmed by the existence of
a doublet in the region of 2850–2920 cm–1 due to the
stretching symmetric (2850 cm–1) and asymmetric
(2920 cm–1) vibrations of the methyl group CH bonds
[7]. The band at 1732–1733 cm–1 in the IR spectra of
these complexes belongs to the stretching vibrations of
carbonyl groups [10].
The prepared complexes III, VI–VIII are blue-
green powders insoluble in water, well soluble in many
organic solvents (benzene, chloroform, acetone etc).
Electron absorption spectra of the synthesized
phthalocyanines registered from their solutions in
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 8 2009

1732
KULINICH et al.
Yields, data of elemental analysis and positions of the bands in electron absorption spectra (benzene solutions) of compounds
IIIa, IIIb Va, Vb–VIIIa, VIIIb
Data of elemental analysis
formula
Positions of bands in electron spectra
Comp.
no.
Yield,
%
found
H
calculated
H N
λmax, nm (log ε)
relative intensity
C
N
C
52.2
50.1
53.0
54.3
74.1
75.2
78.6
76.8
81.1
77.9
55.2 2.4 6.4 С80H40Cl9ErN8O8
63.1 2.5 5.4 С112H56Cl9ErN8O8
62.8 2.8 7.4 С80H42Cl8N8O8
69.6 3.0 5.9 С112H58Cl8N8O8
56.3 2.5 6.3 С82H43Cl8ErN8O10
63.4 2.7 5.3 С114H59Cl8ErN8O10
56.2 2.4 6.5 С82H43Cl8YbN8O10
55.6 2.3 6.5 708, 646 sh, 328
1:0.32:0.40
1:0.45:0.89
IIIa
IIIb
Vа
63.2 2.6 5.3 716, 644 sh, 352
63.0 2.8 7.3 733, 709, 671, 642, 344
69.8 3.0 5.8 739, 716, 676, 650, 356
56.2 2.5 6.4 707 (5.12), 637 sh, 361 (4.8)
63.6 2.7 5.2 718 (5.08), 650 sh, 362 (4.91)
56.0 2.4 6.4 710 (5.18), 640 sh, 362 (4.84)
1:1:0.26:0.25:0.33
1:0.91:0.45:0.40:0.70
Vb
VIа
VIb
VIIа
VIIb
VIIIа
VIIIb
63.3 2.7 5.1 С114H59Cl8YbN8O10 63.5 2.7 5.2 718 (5.15), 652 sh, 352 (4.94)
56.9 2.6 6.3 С85H47Cl8YbN8O10 56.8 2.6 6.2 712 (5.11), 645 sh, 336 (4.79)
63.7 2.9 5.0 С117H63Cl8YbN8O10 63.9 2.9 5.1 719 (5.10), 662 sh, 345 (4.91)
H2Pc(4-t-
699 (5.26), 662 (5.18), 646 sh,
600 sh, 346 (4.84)
Bu)4
benzene are presented in the table and Figs. 2 and 3.
The general view of spectral curves of both non-
metallic compounds Vа, Vb and metallocomplexes
III, VI–VIII are typical of phthalocyanines [11]. They
are characterized by strong long-wave absorption at
708–739 nm from electron π–π* transitions in the
porphirazine macrocycle and by Soret band in the
ultraviolet region (321–362 nm).
decreases from 37 to 24–23 nm. Analogous changes
have been noted for the dinitro-substituted phthalo-
cyanines [13].
In going from the non-metallic compounds Vа, Vb
to the metallocomplexes VI–VIII the splitting of Q-
band disappears. Position of this band in the spectra of
the synthesized lanthanide complexes suffered a red
shift as compared with respective complexes of
bivalent metals, in particularicular, copper [9] and
cobalt [4]; at the same time, it is practically inde-
pendent of the nature of lanthanide and extra ligand
bound with it.
At comparison of the above data with the spectra of
unsubstituted phthalocyanines and of soluble in benzene
t-butyl-substituted phthalocyanines [12] we have to
note a red shift of Q-band that can be due to the
presence in the molecule of the synthesized compounds
electron-withdrawing (chlorine atoms) and electron-
releasing (aryloxy groups) substituents causig the
polarization of the porphirazine macrocycle.
Comparison of electron absorption spectra of
phenoxychloro- (IIIа, VIа–VIIIа) and naphthyloxy-
chloro-substituted (IIIb, VIb–VIIIb) complexes
allows to note two features: red shift of Q-band of
naphthyloxy-substituted compounds (7–11 nm) and
their stronger absorption in the ultraviolet part of the
spectrum. The second feature is connected with
overlapping of low intensity Soret band by the absorp-
tion on account of naphthyloxy group in the same region.
We should specially compare electron absorption
spectra of non-metallic compounds Vа, Vb and the
known t-butyl-substituted phthalocyanine [H2Pc(4-t-
Bu)4] soluble in benzene [12]. This comparison is
reasonable because an alkyl sbstituents as a rule
defines only the solubility but not affects the position
of bands. From the data in the table it is seen that while
the Q-band remains split into two components that is
as known [11] originates from the lower compared to
metallocyanines symmetry of the π-electrons density
distribution in the macrocycle, the splitting value
EXPERIMENTAL
Electron absorption spectra were registered on a
Specord-M40 spectrophotometer at room temperature
in the region of 350–900 nm. As a solvent was used
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ERBIUM AND YTTERBIUM COMPLEXES WITH THE PHTALOCYANINES
1733
benzene. The IR spectra were registered on an Avatar
360 FT–IR spectrophotometer from KBr pellets. The
elemental analysys was carried out on a CHNS-O
Flash EA, 1112 series analyzer. The mass-spectra were
taken on a Saturn 2000 GC/MS instrument. The 13С
NMR spectra were registered on a TESLA BS 587 A
spectrometer.
carbamide was heated to 230–240°С and kept at this
temperature for 30 min. After cooling, the reaction
mixture was ground to powder, washed with distilled
water to the absence of chloride ions, dried and
purified by chromatography on Al2O3 (1st grade of
activity) with the eluent benzene–ethanol, 20:1. The
eluent was distilled off and the residue was dried in a
vacuum at 100°С.
Synthesis of aryloxychlorophthalonitriles IIa,
IIb (general procedure). To a mixture of 1.8 mmol of
tetrachlorophthalonitrile (I) and 8.5 mmol of phenol or
1-naphthol in 30 ml of dimethylsulfoxide at 20–25°С
was added within 2 h 8.5 mmol of lithium hydroxide.
The mixture was stirred for 7 days at room temperature
and then it was poured to 100 ml of water with ice.
The precipitate formed was filtered off and washed
with 5% aqueous sodium hydroxide and then with
water to neutral medium. The completeness of washing
out phenol was verified by negative reaction with a
diazo compound. The compound obtained was dried in
a vacuum at room temperature and then recrystallized
from acetone. Final purification was carried out by
column chromatography with aluminum oxide of 1st
grade of activity, eluent benzene–acetone, 10:1. The
eluent was distilled off and the residue was dried in a
vacuum at room temperature.
Tetra(4,5-diaryloxy-3,6-dichloro)phthalocyanines
(Va, Vb). A mixture of 0.8 mmol of 4,5-diaryloxy-3,6-
dichlorophthalonitrile (IIа, IIb) and 0.1 mmol of
magnesium acetate [Mg(OAc)2·4H2O] was heated to
230–240°С and kept at this temperature for 30 min.
The magnesium complexes IVа, IVb obtained were
extracted with chloroform from the cooled reaction
mixture. After distilling off chloroform the residue was
dissolved in 20 ml of acetic acid (for preparation of
Vа) or in a mixture of acetic acid with pyridine in 1:1
ratio by volume (for preparation of Vb), the solution
was heated at 75–80°С for 1 h, cooled to room
temperature, and poured to 100 ml of water. The
precipitate formed was filtered off, washed with water,
dried, and then purified by chromatography (sorbent
aluminum oxide of 1st grade of activity, eluent
benzene–ethanol, 20:1). After distilling the eluent off
the residue was dried at 90–100°С.
4,5–Diphenoxy-3,6–dichlorophthalonitrile (IIa).
Prepared along the general procedure from 8.5 mmol
of phenol. The product is light-beige powder insoluble
in water, soluble in acetone, chloroform and benzene.
Yield 0.49 g (71.4%), mp 130°С. The IR spectra (KBr
pellets), ν, cm–1: 2237 (νC≡N), 1208 (ν Ar–O–Ar), 749
(νAr–Cl). ЯМР 13С спектр, δ, ppm (CDCl3): 152.1 (Ph–
O–C), 149.8 (C–Ph), 134.5 (C–Cl), 113.5 (C–CN),
125–130 (C–H), 115–116 (C–H), 106.3 (CN). Mass-
spectrum (m/z): 381. Found, %: С 62,6; Н 2,5; N 7,1;
О 8,9. С20Н10Cl2N2О2 Calculated, %: C 63,0; H 2,6; N
7,4; О 8,4.
Erbium and itterbium tetra(4,5-diaryloxy-3,6-
dichloro)phthalocyanine acetates and acetyl-
acetonates (VI–VIII). 1 mmol of compound (Va, Vb)
was dissolved in DMF, 1.5 mmol of metal salt (acetate
or acetylacetonate) was added, and the mixture was
refluxed for 1 h. DMF was then distilled off, the
complexes obtained were extracted from the residue
with benzene and purified by chromatography on a
column with aluminum oxide of the 1st grade of
activity, eluent benzene–ethanol 20:1. The eluent was
then distilled off and the residue was dried in a vacuum
at 50°С for 1 h.
4,5-Dinaphthyloxy-3,6–dichlorophthalonitrile (IIb).
Prepared similarly to compound IIа from 8.5 mmol of
1-naphthol. Light-beige powder insoluble in water,
soluble in acetone, chloroform and benzene. Yield
0.60 g (69.5%), mp 145°C. IR spectrum (KBr pellets,
ν, cm–1): 2235 (νC≡N); 1225 (νAr–O–Ar); 765 (νAr–Cl).
Found, %: С 68,3; Н 2,8; N 5,8; О 6,7. С28Н14Cl2N2О2
Calculated, %: C 69,9; H 2,9; N 5,8; О 6,6.
Yields, data of elemental analysis, and positions of
bands in electron absorption spectra of compounds III,
V–VII are listed in the table.
ACKNOWLEDGMENTS
Chloroerbium tetra(4,5-diaryloxy-3,6-dichloro)-
phthalocyanines (IIIa, IIIb). A mixture of 0.4 mmol
of 4,5-diaryloxy-3,6-dichlorophthalonitrile (IIa, IIb),
0.15 mmol of erbium chloride ErCl3, and 1.6 mmol of
This work was supported financially by Ministry of
Education and Science of Russian Federation (project
RPN 2.1.1.1180).
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KULINICH et al.
8. Levi, G.C. and Nelson, G.L., Carbon-13 Nuclear
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