Nucleophilic substitution in 4-bromo-5-nitrophthalodinitrile: IX. Synthesis of 4-(morpholin-4-yl)-5-aryloxyphthalodinitriles and copper phthalocyanines based thereon

Article abstract of DOI:10.1134/S1070363209050260

Nucleophilic aromatic substitution of bromine in 4-bromo-5- nitrophthalodinitrile with the morpholine residue and the subsequent substitution of nitro group with the aryloxy one yielded 4-morpholyl-5- aryloxyphthalodinitriles. From these substances octasubstituted copper phthalocyanines were synthesized, and their physicochemical properties were studied.

Full text of DOI:10.1134/S1070363209050260

ISSN 1070-3632, Russian Journal of General Chemistry, 2009, Vol. 79, No. 5, pp. 1018–1023. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © A.I. Fedotova, V.E. Maizlish, G.P. Shaposhnikov, C.N. Filimonov, I.G. Abramov, 2009, published in Zhurnal Obshchei Khimii,
2009, Vol. 79, No. 5, pp. 846–851.
Nucleophilic Substitution in 4-Bromo-5-nitrophthalodinitrile:
IX.1 Synthesis of 4-(Morpholin-4-yl)-5-aryloxyphthalodinitriles
and Copper Phthalocyanines Based Thereon
A. I. Fedotovaa, V. E. Maizlisha, G. P. Shaposhnikova, C. N. Filimonovb, and I. G. Abramovb
a Ivanovo State University of Chemical Technology,
pr. Engel’sa 7, Ivanovo 153000 Russia
e-mail: ttoc@isuct.ru
b
Yaroslavl’ State Technical University, Yaroslavl’, Russia
e-mail: abramovig@ystu.ru
Received June 19, 2008
Abstract―Nucleophilic aromatic substitution of bromine in 4-bromo-5-nitrophthalodinitrile with the
morpholine residue and the subsequent substitution of nitro group with the aryloxy one yielded 4-morpholyl-5-
aryloxyphthalodinitriles. From these substances octasubstituted copper phthalocyanines were synthesized, and
their physicochemical properties were studied.
DOI: 10.1134/S1070363209050260
Metal phthalocyanines and their derivatives are
intensely studied during the last fifty years. They are
widely used as pigments and dyes, catalysts, chemical
sensors, nonlinear optic materials, photosensitizers,
and liquid crystalline materials. They also find their
use in medicine and some other branches of science
and technology [2–11].
extension of the of range of phthalocyanine complexes
by compounds containing aryl and heterocyclic frag-
ments in their structure is urgent.
This report deals with the synthesis of 4-morpholyl-
5-aryloxyphthalodinitriles and copper phthalocyanines
obtained therefrom. As known, numerous o-disub-
stituted phthalodinitriles can be prepared on the basis
of highly reactive 4-bromo-5-nitrophthalodinitrile I
[1, 14–23].
Up to now a wide range of substituted metal
phthalocyanines is synthesized, but the reports dealing
with such compouns containing heterocyclic residues
as substituents are scarce [1, 11, 12]. Data on metal
phthalocyanines containing saturated heterocyclic re-
sidues are practically absent. We believe that it is
connected with the absence or difficult availability of
corresponding precursors, in particular of heteryl-
substituted phthalodinitriles. As known, “small” (three-
seven-membered) heterocycles are present in the
structure of the majority of highly effective pharma-
ceuticals, pesticides, dyes, luminophors, and some
other substances of practical use [13]. It was reported
in [8] that aryloxy-substituted zinc phthalocyanines
exhibit the activity in oxidation reactions. Hence,
considering the importance of phthalocyanines as well
as of the “small” heterocyclic compounds, the
The nucleophilic substitution of bromine in 4-
bromo-5-nitrophthalodinitrile I under the action of
morpholine yielded 4-(morpholin-4-yl)-5-nitrophthalo-
dinitrile II [21]. The subsequent nucleophilic
substitution of the nitro group by means of substituted
phenols or 1-(2)-naphthol led to the target phthalo-
dinitriles IIIa–IIIf.
The composition and structure of substituted phthalo-
dinitriles IIIa–IIIe were confirmed by elemental
1
analysis and the IR and H NMR spectroscopy. In the
IR spectra of compounds IIIa–IIIf the majority of
bands characteristic of substituted phthalodinitriles
appeared [24]. Strong band at 2223–2227 cm–1 cor-
responds to the nitrile group vibrations. The absorption
observed at 2852–2933 cm–1 relates to the C–H bond
vibrations of the methylene groups of the saturated
1
For communication VIII, see [1].
1018

NUCLEOPHILIC SUBSTITUTION IN 4-BROMO-5-NITROPHTHALODINITRILE: IX.
O
1019
O
HN
O
NC
NC
Br
NC
N
NC
N
RH
NO2
NC
NO2
NC
R
I
II
IIIa_IIIf
CH3 (IIIc),
CH3
CH3
(IIIa),
(IIIb),
R =
O
O
O
CH3
O
CH3
CH3
O
(IIIe),
(IIId),
(IIIf).
O
CH3
monoazocycle and the alkyl fragments. These bands
increase in intensity for compounds IIIb–IIId
containing the methyl groups. Absorption bands at
1214–1217 cm–1 related to the Ar–O–Ar bond
vibrations were also observed [25]. 1H NMR spectra of
the compounds obtained contain several types of
signals. The protons of the morpholine cycle appeared
at δ 3.30–3.33 and 3.64–3.68 ppm, the protons of the
aromatic rings gave signals at δ 6.85–7.66 ppm, and
the signals of protons belonging to methyl and tert-
butyl groups were observed at 2.24–2.25, 2.35–2.38,
and 1.15 ppm. As expected, the protons of the aliphatic
ring form two groups of signals at 3.30–3.33 ppm and
3.64–3.68 ppm related to the CH2N and CH2O groups
respectively.
The signals of aromatic protons from the phthalo-
dinitrile fragment are observed in the ranges 7.67–7.69
ppm and 7.24–7.26 ppm. These signals correspond to
the protons adjacent to the nitrogen and oxygen atoms
respectively. Signals of the methyl group protons
neighboring to the phenol oxygen atom in the
compounds IIIc, IIId are observed at 2.24–2.35 ppm,
while the methyl groups belonging to the benzene part
of biphenyl fragment give signals at 2.35 ppm in the
case of p-located hydrogen and at 2.38 ppm for the m-
located one. The protons of tert-butyl group in
compound IIIb give rise to a singlet at 1.15 ppm.
Compounds IIIa–IIIf are crystalline substances of
the color varying from light yellow to bright yellow.
O
R
N
O
N
N
N
N
R
N
.
Cu(OAc)2 H2O
N
Cu
N
N
IIIa_IIIf
180_185oC
R
N
N
O
N
R
IVa_IVf
O
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 5 2009

1020
FEDOTOVA et al.
D
D
1
2
3
2
1
400 500 600
700 800 900
400
500
600
700
800
900
λ, nm
λ, nm
Fig. 2. Electron absorption spectra of complex IVa: (1) in
chloroform, (2) in DMF, and (3) in the concentrated
sulfuric acid.
Fig. 1. The electron absorption spectra in DMF, c 2.2×10–5 M,
(1) compound IVa and (2) compound IVe.
They are soluble in the organic solvents like acetone,
chloroform, DMF, ethanol, and their melting points lie
in the range 148–223°C.
IVd) and sulfuric acids. Note that after precipitation of
complexes IVe, IVf from the concentrated sulfuric
acid sulfonic acids are formed. They become well
soluble in the alkaline water solutions and do not
dissolve in the organic solvents.
Metal complexes IVa–IVf were synthesized by the
reaction of corresponding substituted phthalodinitriles
IIIa–IIIf with copper acetate in the presence of
carbamide at 180–185°C for 2 h.
The structure and individuality of the compounds
IVa–IVf were confirmed by elemental analysis, the
electronic and IR spectroscopy. IR spectra of the
compounds synthesized contain the absorption bands
at 2953–2958, 2852–2856, 1736–1739, 1613–1617,
1592–1595, 1491–1493, 1452–1454, 1413–1414,
1250–1253, 1212–1219, 1116–1119, 1102–1108, and
744–746 cm–1 characteristic of substituted metal
phthalocyanines [26]. Absorption bands belonging to
the substituents also are retained. The analysis of the
electron absorption spectra shows that the nature of
sovent influences the character of spectrum and the
location of absorption bands (see Figs. 1, 2, and the
table). It can be presumed that complexes IVa–IVg in
DMF exist mainly in the associated form. The long-
The melt obtained was ground and washed
successively with 5% hydrochloric acid until the
decoloration of filtrate, and then with water until the
neutral reaction. The target products were extracted
with chloroform. Final purification was carried out by
liquid chromatography on Al2O3, elution with
chloroform. Solvent was removed in a vacuum, and the
target product was dried at 80°C.
The complexes obtained are dark green powders
insoluble in water and well soluble in organic solvents
(benzene, chloroform, DMF, acetone) and in the
concentrated hydrochloric (excluding compounds IVc,
Location of the absorption bands in the electron absorption spectra of complexes
λmax, nm (log ε, ratio of intensities)
Comp. no.
DMF (c = 2.2×10–5 M)
chloroform
conc. H2SO4
691, 639, 422, 331 (1:1.05:0.51:1.14)
697 (5.11), 628 (4.49), 428 (4.36), 341 (4.72)
793, 768 (1:0.92)
IVа
IVb
IVc
IVd
IVe
IVf
694, 651, 433, 332 (1:0.61:0.34:1.08)
694, 651, 432, 337 (1:0.63:0.36:1.05)
693, 645, 433, 338 (1:0.60:0.35:1.05)
691, 641, 410, 333 (1:0.85:0.42:1.59)
691, 641, 413, 334 (1:0.85:0.41:1.57)
698 (4.97), 633 (4.15), 430 (4.05), 343 (4.70)
698 (4.93), 628 (4.25), 425 (4.22), 347 (4.80)
698 (4.93), 627 (4.24), 430 (4.21), 335 (4.81)
698 (4.98), 628 (4.34), 426 (4.23), 329 (4.76)
697 (4.98), 627 (4.35), 427 (4.23), 331 (4.75)
794, 768 (1:0.93)
792, 771 (1:0.96)
792, 770 (1:0.96)
785, 768 (1:0.98)
788, 769 (1:0.97)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 5 2009

NUCLEOPHILIC SUBSTITUTION IN 4-BROMO-5-NITROPHTHALODINITRILE: IX.
1021
wave part of the spectrum contains two intense bands
at 691–694 (the monomeric form) and 639–651 ppm
(the associated form). From the ratio of the absorption
band intensities at the equal concentrations of
complexes it can be considered qualitatively which of
the compounds under investigation is more prone to
association in DMF. It was found that compound IVa
was more inclined to association than compounds
IVb–IVf (see Fig. 1).
carbonate, 0.01 mol of substituted phenol or naphthol,
and 30 ml of DMF was stirred at 130–140°C for 3 h.
After cooling to room temperature the reaction mixture
was poured in 100 ml of water, the precipitate obtained
was filtered off, washed with 50 ml of water, and
crystallized from DMF.
4-(Morpholin-4-yl)-5-phenoxyphthalodinitrile
(IIIa). This compound was obtained according to the
general procedure from 0.94 g of phenol. Yield 2.63 g
1
(86%), mp 174–176°C. H NMR spectrum (DMSO-
The complexes obtained exist in chloroform solu-
tion in the monomeric form. Their long-wave absorp-
tion band undergoes small red shift as compared to
DMF solutions (about 5 nm). Nature of the aryl sub-
stituent does not affect practically either the character
of the spectrum or the location of the absorption bands
(see the table).
d6), δ, ppm (J, Hz): 7.67 s (1H), 7.24 s (1H), 7.15 m
(5H, H–Ar), 3.65 t (4H, CH2O, J 4.0), 3.30 t (4H,
CH2N, J 4.0). Found, %: C 70.57; H 5.23; N 13.56.
C18H15N3O2. Calculated, %: C 70.81; H 4.95; N 13.76.
4-(Morpholin-4-yl)-5-(4-tert-butylphenoxy)phtha-
lodinitrile (IIIb). This compound was obtained ac-
cording to the general procedure from 1.50 g of 4-tert-
Using concentrated sulfuric acid instead of the
organic solvent causes the significant red shift of the
absorption bands. Its value is comparable with the
analogous effect on the unsubstituted copper
phthalocyanine. Under these conditions Q-band is split
in two components of the approximately equal
intensity (see Fig. 2 and the table). This effect was
observed previously for the other octasubstituted
copper phthalocyanines [28].
1
butylphenol. Yield 2.66 g (79%), mp 148–150°C. H
NMR spectrum (DMSO-d6), δ, ppm (J, Hz): 7.67 s
(1H), 7.34 d (2H, J 8.3). 7.24 s (1H), 6.85 d (2H, J
8.3), 3.64 br.s (4H, CH2O), 3.33 br.s (4H, CH2N), 1.15
s (9H, t-Bu). Found, %: C 73.64. H 6.34, N 11.42.
C22H23N3O2. Calculated, %: C 73.11, H 6.41, N 11.63.
4-(Morpholin-4-yl)-5-{[3,4'-dimethyl(1,1'-biphe-
nyl)-4-yl]oxy}phthalodinitrile (IIIc). This compound
was obtained according to the general procedure from
1.98 g of 3,4'-dimethyl-(1,1'-biphenyl)-4-ol. Yield 3.19
Testing of complexes obtained as dyes soluble in
the organic media showed that they paint the polymers
and waxes in the intense green color.
1
g (78%), mp 221–223°C. H NMR spectrum (DMSO-
d6), δ, ppm (J,Hz): 7.69 c (1H, H3), 7.66 d (1H, H2, J
1.0), 7.57 d (2H, J 7.9), 7.51 d.d (1H, J 1.0, 8.5), 7.26
d (2H, J 7.9), 7.25 s (1H), 7.00 d (1H, J 8.5), 3.68 t
(4H, CH2O, J 4.2), 3.31 t (4H, CH2N, J 4.2), 2.35 s
(3H, Me), 2.24 s (3H, Me). Found, %: C 76.42, H
5.45, N 10.50. C26H23N3O2. Calculated, %: C 76.26, H
5.56, N 10.26.
EXPERIMENTAL
The electron absorption spectra were obtained on a
Hithachi U-2001 spectrophotometer in DMF, in
chloroform, and in the concentrated sulfuric acid at
room temperature in the range 325–900 nm. IR spectra
were registered on an Avatar 360 FT-IR ESP spec-
trometer in the range 400–4000 cm–1 in thin layer
(chloroform). 1H NMR spectra were taken on a
Brucker DPX-500 spectrometer (500.17 MHz) in
DMSO-d6. Chemical shifts are presented in the δ-scale
against TMS. Elemental analyses of the compounds
obtained were carried out on the CHNS–O FlashEA
1112 series analyzer.
4-(Morpholin-4-yl)-5-{[3,3-dimethyl(1,1'-biphe-
nyl)-4-yl]oxy}phthalodinitrile (IIId). This compound
was prepared according to the general procedure from
1.98 g of 3,3'-dimethyl-(1,1'-biphenyl)-4-ol. Yield 3.32 g
1
(81%), mp 207–209°C. H NMR spectrum (DMSO-
d6), δ, ppm: 7.69 s (1H), 7.67 d (1H, J 1.2), 7.52 d.d
(1H, J 1.2, 8.5), 7.49 s (1H), 7.45 d (1H, J 7.9), 7.38 t
(1H, J 7.9), 7.26 s (1H), 7.17 d (1H, J 7.9), 7.01 d (1H,
J 8.5), 3.68 t (4H, CH2O, J 4.3), 3.30 t (4H, CH2N, J
4.3), 2.38 s (3H), 2.25 s (3H). Found, %: C 76.35, H
5.72, N 10.52. C26H23N3O2. Calculated, %: C 76.26, H
5.66, N 10.26.
4-Bromo-5-nitro (I) and 4-(morpholin-4-yl)-5-
nitrophthalodinitrile (II) were obtained according to
[29] and [21] respectively.
4-(Morpholin-4-yl)-5-aryloxyphthalodinitriles (IIIa-
IIIf) (general procedure). A mixture of 0.01 mol of
compound II, 0.02 mol of the anhydrous potassium
4-(Morpholin-4-yl)-5-(1-naphthyloxy)phthalodi-
nitrile (IIIe). This compound was obtained according
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 5 2009

1022
FEDOTOVA et al.
to the general procedure from 1.98 g of 1-naphthol.
Yield 2.58 g (78%), mp 161–162°C. Found, %: C
72.78, H 5.21, N 12.60. C20H17N3O2. Calculated, %: C
72.49, H 5.17, N 12.68.
(IVd). This compound was prepared from 205 mg of
compound IIId. Yield 87.6 mg (41%). Found, %: C
73.69, H 5.56, N 10.90. C104H92N12O8Cu. Calculated,
%: C 73.41, H 5.45, N 9.88.
Copper tetra-4-(morpholin-4-yl)-tetra-5-(1-na-
phthyloxy)phthalocyanine (IVe). This compound was
prepared according to the general procedure from
118 mg of the compound IIIe Yield 60.1 mg (49%).
Found, %: C 68.98, H 5.01, N 11.89. C80H68N12O8Cu.
Calculated, %: C 69.18, H 4.93, N 12.10.
4-(Morpholin-4-yl)-5-(2-naphthyloxy)phthalodi-
nitrile (IIIf). This compound was obtained according
to the general procedure from 1.44 g of 2-naphthol.
Yield 2.74 (83%), mp 190–192°C. Found, %: C 72.70,
H 5.21, N 12.55. C20H17N3O2. Calculated, %: C 72.49,
H 5.17, N 12.68.
Copper tetra-4-(morpholin-4-yl)-tetra-5-(2-na-
phthyloxy)phthalocyanine (IVf). This compound was
prepared according to the general procedure from
118 mg of the compound IIIf. Yield 57.5 mg (47%).
Found, %: C 69.37, H 5.09, N 11.89. C80H68N12O8Cu.
Calculated, %: C 69.18, H 4.93, N 12.10.
Copper tetra-4-(morpholin-4-yl)-tetra-5-aryloxy-
phthalocyanines (IVa–IVe) (general procedure). A
batch of substituted phthalodinitrile, 0.5 mmol, was
thoroughly ground with 0.14 mmol of copper acetate
dihydrate and 1 mmol of carbamide. The mixture ob-
tained was heated to 180–185°C and kept for 2 h. The
reaction mixture was washed successively with 5%
hydrochloric acid until the decoloration of the filtrate,
and then with water until the neutral reaction of the
medium. The target products were extracted with
chloroform. Final purification was carried out by
column chromatography on Al2O3, elution with chloro-
form. Solvent was distilled off in a vacuum, and the
target product was dried at 80°C. The complexes
obtained are dark green powders insoluble in water and
soluble in the organic solvents.
ACKNOWLEDGMENTS
The work was carried out with the financial support
of the Ministry of Science and Education of the
Russian Federation (no. RNP 2.2.1.1.7280, no. RNP
2.1.1.1180).
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