Synthesis and properties of 2,3,9,10,16,17,23,24-octakis(3-phenoxyphenoxy)phthalocyanine and its complexes with erbium of diverse structures

Article abstract of DOI:10.1134/S1070428016020172

Reaction of 4,5-dichlorophthalonitrile with 3-phenoxyphenol led to the formation of 4,5-bis(3-phenoxyphenoxy)phthalonitrile. It has underlain the synthesis of 2,3,9,10,16,17,23,24-octakis(3-phenoxy-phenoxy) phthalocyanine and its single and double deck sandwich complexes with erbium. As show the electron absorption spectra the complexes are dissociated in dichloromethane at concentrations below 1 × 10^-5 mol L^-1.

Full text of DOI:10.1134/S1070428016020172

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2016, Vol. 52, No. 2, pp. 261–267. © Pleiades Publishing, Ltd., 2016.
Original Russian Text © A.I. Koptyaev, E.S. Ageeva, N.E. Galanin, G.P. Shaposhnikov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52,
No. 2, pp. 278–283.
Synthesis and Properties of 2,3,9,10,16,17,23,24-Octakis(3-
phenoxyphenoxy)phthalocyanine
and Its Complexes with Erbium of Diverse Structures
A. I. Koptyaev, E. S. Ageeva, N. E. Galanin, and G. P. Shaposhnikov
Research Institute of Macroheterocyclic Compounds at Ivanovo State University of Chemical Engineering,
pr. Sheremetevskii 7, Ivanovo, 153000 Russia
e-mail: nik-galanin@yandex.ru
Received July 4, 2015
Abstract—Reaction of 4,5-dichlorophthalonitrile with 3-phenoxyphenol led to the formation of 4,5-bis(3-
phenoxyphenoxy)phthalonitrile. It has underlain the synthesis of 2,3,9,10,16,17,23,24-octakis(3-phenoxy-
phenoxy)phthalocyanine and its single and double deck sandwich complexes with erbium. As show the electron
absorption spectra the complexes are dissociated in dichloromethane at concentrations below 1 × 10–5 mol L–1.
DOI: 10.1134/S1070428016020172
Phthalocyanines are among the most important
specimens of the large class of tetrapyrrole macro-
heterocycles. Substituted phthalocyanines are used as
catalysts and photocatalysts [1, 2], liquid crystalline
materials [3], in xerography [4], optics [5], in the
technique of solar energy transformation [6].
ly affects phthalocyanines properties, for instance,
their spectral and luminescence characteristics [11].
We report here on a synthesis and properties of
phthalocyanines containing 3-phenoxyphenoxyl substi-
tuents that to a large extent hamper the association of
phthalocyanines in dichloromethane solution. As an
initial compound for the synthesis served 4,5-bis(3-phe-
noxyphenoxy)phthalonitrile 1 prepared from 4,5-dichloro-
phthalonitrile and 3-phenoxyphenol 2. Compound 2
was obtained in reaction of resorcinol with iodoben-
zene in DMF in the presence of K2CO3 catalyzed with the
Cu2Cl2 complex with 8-hydro-xyquinoline (Scheme 1).
Unsubstituted phthalocyanine and their metal comp-
lexes are characterized by extremely low solubility in
most organic solvents. To increase the solubility favoring
the isolation of phthalocyanines in the individual state,
facilitating the identification and extending the appli-
cation possibilities bulky hydrophobic substituents are
introduced in the composition of these substances, e.g.,
alkoxy [7] or aryloxy groups [8].
In a known procedure phenol 2 was obtained from
bromobenzene by heating at 120°С for 45 min in 82%
yield [12]. The process was catalyzed by Cu2Cl2
complex with α,α-bipyridyl. The replacement of bro-
mobenzene with iodobenzene made it possible to
Many phthalocyanines soluble in organic media were
shown to be prone to association in solutions in low
polar organic solvents [9, 10]. The association significant-
Scheme 1.
Cl
Cl
CN
CN
NC
NC
O
O
OPh
OPh
HO
OH
PhO
OH
K2CO3
PhI, K2CO3
CuCl2_8-hydroxyquinoline
2
1
261

KOPTYAEV et al.
262
Scheme 2.
R
R
R
R
R
R
R
R
N
N
NC
NC
O
O
O
1. H13C6OH,
H13C6OLi
2. AcOH
Cl
N
N
N
N
N
HN
N
.
ErCl3 6H2O
Er
N
4
N
N
N
N
NH
N
O
R
R
R
R
1
R
R
R
R
3
O
O
.
R =
shorten the reaction time to 30 min, to reduce the
temperature to 100°С, and to use more accessible
catalyst obtaining compound 2 in 80% yield.
Compound 2 is a viscous light yellow fluid solidifying
at storage. Its structure was confirmed by the 1Н NMR
spectrum, and physical characteristics were completely
consistent with the published data [13].
tomeric forms of compound 1, which we describe as
“open” and “closed”. They significantly differ by the geo-
metric structure and the enthalpy of formation (Fig. 1).
We believe that in CDCl3 compound 1 exists to 67% in the
more thermodynamically favorable “closed” form and
to 33% in the “open” form.
In the mass spectra MALDI-TOF of nitrile 1 three
main signals are present, m/z 496.26, 543.38, and
574.45 Da, corresponding to the molecular ion [M]+
and its adducts with two sodium ions [M + 2Na]+ and
two potassium ions [M + 2K]+ respectively.
The composition and structure of nitrile 1 was
1
confirmed by elemental analysis, Н NMR and mass
1
spectra. Н NMR spectrum of nitrile 1 recorded in
CDCl3 contains several groups of signals. The ratio of their
integral intensities corresponding to thirty and not twenty
protons, and the doubling of some signals suggests that the
nitrile is present in the solution as two stable tautomers in
the ratio 2 : 1. Quantum-chemical calculations by АМ1
method actually showed the existence of two stable tau-
The heating of nitrile 1 in the presence of lithium 1-
hexanolate followed by treating with acetic acid
afforded in 68% yield 2,3,9,10,16,17,23,24-octakis(3-
phenoxyphenoxy)phthalocyanine 3. Its single deck
complex 4 with erbium was obtained by boiling
(a)
(b)
Fig. 1. Tautomeric forms of 4,5-bis(3-phenoxyphenoxy)phthalonitrile 1 according to calculations by АМ1 method: “open,” ΔHf
430.96 kJ mol–1 (а), “closed,” ΔHf 357.36 kJ mol–1 (b).
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SYNTHESIS AND PROPERTIES OF 2,3,9,10,16,17,23,24-OCTAKIS(3-PHENOXYPHENOXY)...
263
Scheme 3.
R
R
R
R
N
N
N
N
N
N
N
N
NC
NC
O
O
O
R
R
R
R
1. H17C8OH, H17C8OLi
2. 0.15 equiv ErCl3
R
R
R
R
Er
N
O
N
N
N
N
1
N
N
N
R
R
5
R
R
O
O
.
R =
phthalocyanine 3 with excess erbium chloride in a
mixture DMF–toluene, 9 : 1, yield 72% (Scheme 2).
The mass spectra of metal-free phthalocyanine 3
and of double-deck complex 5 contain the peaks of
their molecular ions, their fragment ions, and adducts
with K and Na. In the mass spectrum of single deck
complex 4 a cluster was observed in the region
2306.75–2313.08 Da corresponding to the ion [M – Cl +
154]–, an adduct of dechlorinated molecular ion with
the matrix, (2,5-dihydroxybenzoic acid).
This reaction was carried out in solution since at
melting the mixture of nitrile 1 with the metal salt accor-
ding to the mass spectrum a mixture formed of phthalo-
cyanine 3 free of metal and its single deck and double deck
complexes impossible to separate by chromatography.
The synthesis of the double deck erbium complex 5
was performed by the reaction of dilithium phthalo-
cyanine obtained by boiling nitrile 1 in 1-octanol in the
presence of lithium 1-octanolate, with erbium chloride
calcined at 200°С for 2 h (Scheme 3), yield of complex
5 57%.
In the 1Н NMR spectrum of phthalocyanine 3 taken
in CDCl3 four groups of signals are present. Two
multiplets (7.73–7.81 and 8.17–8.24 ppm of integral
intensity 1 : 1) correspond to the resonance of the eight
protons of benzene rings of the macrocycle, a multiplet
at 7.35–7.43 ppm originates from the resonance of 32
protons of benzene rings close to the macrocycle, and
the multiplet at 7.00–7.21 ppm belongs to the other 40
protons. The splitting of the signals of equivalent
protons of the benzene rings of the macrocycle
indicates that compound 3, like nitrile 1, in solution
exists in the form of several tautomers.
Compounds 3 and 5 were isolated by distilling off
the solvents at a reduced pressure, the residues were
washed with dilute acetic acid and water, and dried.
The substances were purified by column chromato-
graphy. In order to isolate and purify complex 4 its
solution in DMF–toluene mixture was diluted with
water, the complex was extracted with toluene and
chromatographed on a column.
1
It was shown previously when studying by Н
NMR method erbium complexes of various structures
with crown-substituted phthalocyanines [14, 15] that in
the spectrum of such single deck erbium complex con-
taining as extra ligands an acetate ion and a molecule
of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) a strong
All phthalocyanines synthesized are dark green
powders. Their composition and structure are confir-
med by elemental analysis, MALDI-TOF mass
spectrometry, 1Н NMR and electronic spectra.
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KOPTYAEV et al.
264
0.5
0.5
A
A
A
2
A
4
1
1
1
0.4
0.4
2
2
1.0
1.0
3
0.3
0.3
0.2
0.2
0.5
0.5
0.1
0.1
0.0
0.0
0.0
400
0.0
400
400
500
500
600
600
700
700
800
800
400
500
500
600
600
700
700
800
800
λ, нм
λ, nm
λλ,,нnмm
Fig. 2. Electron absorption spectra of phthalocyanine 3 and
complex 4 in dichloromethane.
Fig. 3. Electron absorption spectra of complex 5 in dichlo-
romethane (1), in a mixture DMF + 1% NH2NH2·H2O (2).
downfield shift was observed for the proton signals of
the benzene rings of the macrocycle (24.51 ppm)
originating from the paramagnetic nature of the metal
[14, 15]. In our case an opposite trend was observed.
The signal of eight protons of the benzene rings was
found in the strong field at 1.99 ppm, the signals of 16
protons close to the macrocycle in the ortho-positions
of the phenylene rings were observed at 3.17 ppm, and
the signals of the rest 56 protons distant from the coor-
dination node appeared in the region 7.50–15.00 ppm.
Evidently the reason of this strongly different spectral
characteristics of the phthalocyanines originates from
the difference in the coordination surrounding of the
erbium ion since as known erbium contained in
complex compounds depending on the chemical
structure of the ligands can shift the proton signals of
the latter both downfield and upfield [16, 17].
and therefore the dπ–pπ interaction decreases and the σ-
interaction metal–phthalocyanine increases resulting in
the blue shift of the maxima of the absorption bands.
The character of electron absorption spectra of
double deck complex 5 depends on the solvent nature.
In dichloromethane the absorption spectrum of com-
pound 5 (Fig. 3, 1) by the character and the absorption
bands maxima is close to the spectrum of single deck
complex 4, only the maximum of the Q bands suffers a
minor (6 nm) blue shift. Besides, in the region 450–
500 nm of the spectrum a wide band of low intensity
appears characteristic of neutral radical “green” forms of
lanthanide sandwich complexes [19]. In DMF
containing 1% of hydrazine hydrate as reducer the
electron absorption spectrum of complex 5 (Fig. 3, 2)
is changed. In the longwave region it is transformed in
two bands with the maxima at 684 and 628 nm, therewith
the shortwave component becomes the stronger, and
the wide band in the region 450–500 nm disappears.
This indicates the conversion of complex 5 in the
presence of a reducer into the anionic “blue” form.
Electron absorption spectra of phthalocyanine 3 and
single deck complex 4 are presented in Fig. 2. The
comparison of the spectra of compounds 3 and 4 with
the absorption spectra of similar in structure
2,3,9,10,16,17,23,24-octakis[3-(trifluoromethyl)phe-
noxy]phthalocyanine and its complex with indium [18]
shows that the replacement of the trifluoromethyl
substituent by a phenoxy group results in a small (3–
5 nm) red shift in the maxima of the absorption bands in
the spectrum of compound 3 and to a more significant
(16–20 nm) blue shift in the spectrum of complex 4.
The blue shift in the latter case is evidently due to the
nature of the metal cation. The erbium ion possessing a
much larger ionic radius than indium ion apparently is
outside of the coordination sphere of the macrocycle
The fluorescence spectrum of metal-free
phthalocyanine 3 (Fig. 4) contains a strong band with a
maximum at 710 nm accompanied with two overtones
at 742 and 788 nm. The fluorescence spectrum of complex
4 is characterized by a band at 698 nm with an overtone
at 755 nm. The fluorescence of sandwich type lanthanide
complexes is known to be either less intensive [20] or
totally absent [14] as compared to the lanthanides mo-
nophthalocyaninates. As expected, sandwich complex 5
in toluene does not exhibit a notable luminescence.
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SYNTHESIS AND PROPERTIES OF 2,3,9,10,16,17,23,24-OCTAKIS(3-PHENOXYPHENOXY)...
265
F,
F,
rel. un.
отн. ед.
A
A
2.5
2.5
2
1
1.0
1.0
2.0
4
2.0
3
Y = 0.09+169181.57*X
Y = 0.09 + 169181.57·Х
0.8
0.8
R = 0.9981
r 0.9981
1.5
1.5
0.6
0.6
1.0
1.0
0.4
0.4
Y = 0.05+86092.75*X
Y = 0.05 + 86092.75·Х
0.5
0.5
R = 0.9996
r 0.9996
0.2
0.2
0.0
0.0
0.0
650
0.0
1.0
2.0
3.0
4.0
5.0
0.0
с·10–5, mol L–1
650
700
700
750
750
800
800
λ, нм
λ, nm
Fig. 4. Normalized fluorescence spectra in toluene of com-
pounds 3 and 4.
Fig. 5. Optical density of phthalocyanines 3 (■) and 5 (●) solu-
tions in dichloromethane as a function of their concentration.
The character of electron absorption spectra of the
synthesized phthalocyanines permits a conclusion that
in dichloromethane they are not associated at a
concentration (2–5) × 10–6 mol L–1. To find out the
con-centration value when the association becomes
significant we measured the variation of the optical
density of phthalocyanine solutions in dichloro-
methane as a function of concentration for the
longwave component of Q bands. These dependences
for metal-free phthalocyanine 3 and double deck
complex 5 are presented in Fig. 5.
Zeta, fluorescence spectra, on a spectrofluorimeter
Solar CM 2203 (λex 640 nm), Н NMR spectra, on a
1
spectrometer Bruker Avance-500 in CDCl3 (internal
reference TMS). Mass spectra (MALDI-TOF, matrix
2,5-dihydroxybenzoic acid) were measured on an
instrument Shimadzu AXIMA Confidence. Elemental
analysis was carried out on a FlashEA 1112 CHNS–O
Analyzer.
Electron absorption spectra were measured in
quartz cells of optic path length 10 mm at 295 K. In
spectral experiments dichloromethane and toluene of
chemically pure grade were used obtained from Ekos-1.
Iodobenzene (98%) and 4,5-dichlorophthalonitrile
(99%) (Sigma-Aldrich) were used without additional
treatment.
As seen, in the range of low concentrations the
optical density linearly depends on the concentration,
namely, the compounds exist in dichloromethane in the
monomeric form. The association becomes important
at the concentrations of compounds 3–5 in dichlorome-
thane of ~1.67 × 10–5, 1.88 × 10–5, and 1.11 × 10–5 mol L–1
respectively (the concentrations has been calculated by
extrapolation of linear and nonlinear parts of the plots).
4,5-Bis(3-phenoxyphenoxy)phthalonitrile (1). A
mixture of 1.0 g (5.1 mmol) of 4,5-dichlorophthalo-
nitrile, 1.9 g (10.2 mmol) of 3-phenoxyphenol 2, 4.0 g
(29 mmol) of K2CO3, and 30 mL of DMF was stirred
for 5 h at 110°С, cooled, diluted with 200 mL of water,
the separated precipitate was filtered off, washed with
40 mL of 2% solution of KOH, then with water till рН 7,
and dried. Yield 2.2 g (88%), wax-like light brown
substance, soluble in benzene, chloroform, acetone,
Thus we synthesized 2,3,9,10,16,17,23,24-octakis-
(3-phenoxyphenoxy)phthalocyanine and its single deck
and double deck sandwich erbium complexes. All
obtained compounds are not associated in dichloro-
methane at concentrations below 1.11 × 10–5 mol L–1
and the sandwich type complex is the most prone to
association.
1
DMF. Н NMR spectrum, δ, ppm: 7.43–7.34 m (8Н),
7.27 s (2Н), 7.21–7.04 m (10Н), 6.95–6.93 m (2Н),
6.81–6.79 m (2Н), 6.74 s (2Н), 6.59–6.53 m (4Н). Mass
spectrum, m/z: 496.26 [M]+, 543.38 [M + Н + 2Na]+,
574.45 [M + 2K]+. Found, %: C 77.57; H 4.10; N 5.36.
C32H20N2O4. Calculated, %: C 77.41; H 4.06; N 5.64.
M 496.14.
EXPERIMENTAL
Electron absorption spectra of compounds under
study were recorded on a spectrophotometer Helos
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KOPTYAEV et al.
266
3-Phenoxyphenol (2). A mixture of 10.2 g (50 mmol)
on a column packed with silica gel Kieselgel 60
(Merck) (eluent toluene), collecting the main (second)
green zone. Yield 0.04 g (72%), dark green powder,
soluble in benzene, toluene, dichloromethane, sparingly
soluble in DMF, acetone. Electron absorption spectrum,
of iodobenzene, 6.6 g (60 mmol) of resorcinol, 10.3 g
(70 mmol) of K2CO3, 0.05 g (0.5 mmol) of copper(I)
chloride, 0.07 g (0.5 mmol) of 8-hydroxyquinoline,
and 60 mL of DMF was stirred for 30 min at 100°С,
cooled, diluted with 200 mL of water, acidified with
sulfuric acid to рН 2, and extracted with 150 mL of
benzene. The organic layer was separated, the reaction
product was extracted with 15% solution of NaOH, the
alkaline solution was acidified with sulfuric acid to рН 1,
the separated precipitate was filtered off, dissolved in
benzene and washed with water till negative test for
resorcinol (test with FeCl3). The solvent was distilled
off. Yield 7.4 g (80%), light-yellow fluid, nD20 1.6010
[13]. 1Н NMR spectrum, δ, ppm: 5.45 br.s (1Н), 6.53 s
(1Н), 6.59–6.62 t (2Н, J 7.3 Hz), 7.06–7.08 d (2Н, J
8.1 Hz), 7.16–7.17 t (1Н, J 6.9 Hz), 7.18–7.22 t (1Н, J
7.3 Hz), 7.36–7.39 t (2Н, J 7.2 Hz).
λ
max, nm (log ε) in CH2Cl2: 359 (4.94), 612 (4.22), 647
1
(sh), 678 (5.30). Н NMR spectrum, δ, ppm: 1.99 br.s
(8Н). 15.2–7.50 br.s (56Н), 3.17 br.s (16Н). Mass
spectrum, m/z: 2306.75–2313.08 [M – Cl + 154]+.
Found, %: C 70.93; H 3.81; N 4.83. C128H80ClErN8O16.
Calculated, %: C 70.24; H 3.68; N 5.12. М 2185.47.
Bis[2,3,9,10,16,17,23,24-octakis(3-phenoxyphe-
noxy)phthalocyaninato]erbium (5). To a boiling so-
lution of 0.2 g of lithium in 50 mL of anhydrous 1-
octanol was added 0.50 g (1.0 mmol) of nitrile 1, the
mixture was maintained for 3 h, 0.04 g (0.15 mmol) of
anhydrous erbium chloride was added, the mixture was
maintained for another 4 h, the solvent was distilled
off, the reaction mass was dispersed in 50 mL of 50%
acetic acid solution, filtered off, washed with 20 mL of
10% ammonia solution, 50 mL of water, and dried.
The residue was dissolved in dichloromethane and
chromatographed on a column packed with silica gel
Kieselgel 60 (Merck) (eluent dichloromethane), collec-
ting the main green zone. Yield 0.30 g (57%), dark
green powder, soluble in benzene, toluene, dichloro-
methane, DMF, sparingly soluble in acetone. Electron
absorption spectrum, λmax, nm (log ε) in CH2Cl2: 671
(5.08), 608 (4.58), 481 (3.55), 351 (5.17); in DMF +
1% N2H4·H2O: 684 (4.71), 628 (4.99), 349 (5.12).
Mass spectrum, m/z: 4236.20 [M + 2K + Na]+, 4135.88
[M + H]+, 3954.45 [M – OPhOPh + 2H]+, 3770.16 [M –
2OPhOPh + H]+. Found, %: C 75.01; H 3.98; N 4.97.
2,3,9,10,16,17,23,24-Octakis(3-phenoxypheno-
xy)phthalocyanine (3). To a boiling solution of 0.2 g
of lithium in 50 mL of anhydrous 1-hexanol was added
0.5 g (1.0 mmol) of nitrile 1, the mixture was main-
tained for 3 h, the solvent was distilled off, the reaction
mass was dispersed in 50 mL of 50% acetic acid
solution, filtered off, washed with 20 mL of 10%
ammonia solution, 50 mL of water, and dried. The
residue was dissolved in dichloromethane and chroma-
tographed on a column packed with silica gel Kieselgel
60 (Merck) (eluent dichloromethane), collecting the
main green zone. Yield 0.34 g (68%), dark green powder,
soluble in benzene, toluene, dichloromethane, sparingly
soluble in DMF, acetone. Electron absorption spec-
trum, λmax, nm (log ε) in CH2Cl2: 348 (4.96), 607
1
C256H160ErN16O32. Calculated, %: C 74.28; H 3.90; N
(4.50), 638 (4.71), 666 (5.19), 701 (5.27). Н NMR
5.41. М 4135.07.
spectrum, δ, ppm: –0.79 br.s (2Н), 7.00–7.21 m (40Н),
7.35–7.43 m (32Н), 7.73–7.81 m (4Н), 8.17–8.24 m
(4Н). Mass spectrum, m/z: 1986.76 [M]+, 1845.94 [M –
OPhOPh + 3H + K]+, 1802.93 [M – OPhOPh]+,
1705.06 [M – 2OPhOPh + 2Na + K]+, 1619.01 [M –
2OPhOPh]+, 1188.89 [M – OPhOPh + 2Na + K]+.
Found, %: C 77.88; H 4.31; N 5.12. C128H82N8O16.
Calculated, %: C 77.33; H 4.16; N 5.64. М 1986.58.
The study was carried out under the financial
support of the Russian Science Foundation (contract
no. 14-23-00204).
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