Molecular design of new magnetically active copper complexes with heteroaromatic schiff bases and azo compounds

Article abstract of DOI:10.1134/S1070363208060224

Copper chelates with tridentate ligands containing pyridine or pyrazole ring at the azomethine or azo fragment were synthesized by chemical electrochemical methods, and their structure was characterized by the EXAFS spectra. Thermal magnetochemical analys

Full text of DOI:10.1134/S1070363208060224

ISSN 1070-3632, Russian Journal of General Chemistry, 2008, Vol. 78, No. 6, pp. 1230–1235. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © A.S. Burlov, A.I. Uraev, V.N. Ikorskii, S.A. Nikolaevskii, Yu.V. Koshchienko, I.S. Vasil’chenko, D.A. Garnovskii, V.G. Vlasenko,
Ya.V. Zubavichus, L.N. Divaeva, G.S. Borodkin, A.D. Garnovskii, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 6, pp. 1002–1007.
Molecular Design of New Magnetically Active Copper Complexes
with Heteroaromatic Schiff Bases and Azo Compounds
A. S. Burlova, A. I. Uraeva, V. N. Ikorskii†b, S. A. Nikolaevskiia, Yu. V. Koshchienkoa,
I. S. Vasil’chenkoa, D. A. Garnovskiic, V. G. Vlasenkod, Ya. V. Zubavichuse, L. N. Divaevaa,
G. S. Borodkina, and A. D. Garnovskiia
a Research Institute of Physical and Organic Chemistry, Southern Federal University,
pr. Stachki 194/2, Rostov-on-Don, 344090, Russia
e-mail: garn@ipoc.rsu.ru
b International Tomographic Center, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russia
c Southern Research Center, Russian Academy of Sciences, Rostov-on-Don, Russia
d Research Institute of Physics, Southern Federal University, Rostov-on-Don, Russia
e “Kurchatovskii institute” Russian Research Center, Moscow, Russia
Received August 30, 2007
Abstract—Copper chelates with tridentate ligands containing pyridine or pyrazole ring at the azomethine or
azo fragment were synthesized by chemical electrochemical methods, and their structure was characterized by
the EXAFS spectra. Thermal magnetochemical analysis of the complexes revealed antiferromagnetic exchange
interaction in all complexes. The exchange interaction parameter of the complex containing an N-tosylamino
group in the ortho position with respect to the azomethine group is much lesser than that of the corresponding
complex having an oxygen atom in the same position. The copper chelate derived from azopyrazole ligand
shows low-temperature ferromagnetic phase transition.
DOI: 10.1134/S1070363208060224
Molecular design principles [1–5] are widely used
in the creation of magnetically active metal complexes
of Schiff bases and their analogs [6–10]. Such
complexes are usually [4, 5] synthesized from ligands
of general structure I where aldehyde (R) and amine
(R') components, donor atoms X, and fragments Y are
varied. In continuation of our previous studies [11–15]
we synthesized and characterized tridentate hetero-
cyclic ligands, Schiff base II and azo pyrazole III.
Ligands II and III were used to obtain dinuclear
complexes IV and V, and the structure and magnetic
properties of the latter were examined.
OH
N
N
N
OH
Me
H
OH
N
O
N
N
Ph
II
III
Schiff base II exists mainly in the enol form [4, 5],
while hydrazone tautomer III is typical of the azo
pyrazole ligand [5, 16]. The corresponding coordina-
tion copper compounds have the composition Cu2L2
(where LH2 is ligand II or III) and chelate structure
with almost equivalent metal–ligand bonds, which
excludes (cf. [5, 17, 18]) consideration of tautomeric
anionic ligand systems. The chelate structure follows
from the IR spectra of complexes IV and V, which
lack OH and NH stretching vibration bands in the
region 3100–3400 cm–1; the frequency of stretching
vibrations of the C=N group in the complexes
R
X
H
Y N
R
R'
I
I, R = Alk, Ar, Ht; R′ = Alk, Ar, Ht; X = NR2, O, S, Se; Y = CR3,
N; R2 = H, Alk, Ar, Ts; R3 = H, Alk, Ar; Ts = p-MeC6H4SO2.
† Deceased.
1230

MOLECULAR DESIGN OF NEW MAGNETICALLY ACTIVE COPPER COMPLEXES
1231
N
Ph
N
O
O
N
X
X
N
N
N
N
O
O
O
Me
N
Cu
Cu
Cu
Cu
N
Me
O
N
N
N
Ph
IV
V
IV, X = O (a); X = NTs (b).
decreased by 10–15 cm–1, while the Ph–O vibration
frequency increases by 50 cm–1, as compared to the
corresponding free ligands [19, 20]. The complexes
synthesized by chemical and electrochemical methods
had identical spectral parameters.
nearest environment of the copper ion in complexes
IVb and V are collected in table. They were obtained
by fitting the χ(k) values calculated for the
corresponding model structures to the exsperimental
EXAFS spectra. As model structure we used bis[4-(5-
chloro-2-hydroxyphenylimino)pent-2-en-2-olato]dicop-
per(II) [21] with the distances Cu–O 1.94 and 1.95 Å
and Cu–Cu 2.994 Å.
The dinuclear structure and coordination mode
were determined by analysis of the EXAFS spectra of
complexes IVb and V. The CuK-edge XANES spectra
of V and IVb (Fig. 1) displayed very weak near-edge
peaks A at 8977.5 eV, a well resolved shoulder B at
8987 eV, and the main absorption maximum C at
8998 eV. This pattern results from electron transitions
1s → 3d, 1s → 4s, and 1s → 4p+ligand orbitals,
respectively. The first derivatives of the CuK-edges for
compounds IVb and V are characterized by distinctly
split maxima, which is typical of planar coordination
of copper ion.
The Fourier transforms of both samples (Fig. 2)
consist of the main peak at r = 1.55 Å and a peak with
a lower amplitude at r = 2.66 Å (IVb) or 2.36 Å (V).
The main peak corresponds to photoelectron scattering
at the nearest coordination spheres of nitrogen and
oxygen, whose radii were determined by fitting (see
table). The radii of the first coordination sphere are
typical of structurally related copper complexes. The
second peak, in keeping with the proposed dinuclear
structure, can be assigned to the Cu–Cu distance. It
should be noted that the Cu–Cu distance in complex V
Figure 2 shows Fourier transforms of the CuK-edge
EXAFS spectra of IVb and V. Parameters of the
Cu–N/O
28
C
Cu–Cu
24
μ
B
2.5
2.0
1.5
1.0
0.5
0.0
20
2
A
2
16
12
8
1
4
1
0
0
1
2
3
4
5
6
7
8
8900 8950
9000
9050
9100 9150
E, eV
r, Å
Fig. 2. Fourier transforms (circled lines) of the CuK-edge
EXAFS spectra (solid lines) of complexes (1) IVb and (2) V.
Fig. 1. CuK-edge XANES spectra (solid lines) and their first
derivatives (dotted lines) of complexes (1) IVb and (2) V.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 78 No. 6 2008

1232
BURLOV et al.
χ, cm3 mol–1
2.4
2.2
0.025
0.020
0.015
0.010
0.005
0.000
2.0
2.5
2.0
1.5
1.0
1.8
1.6
1.4
1.2
1.0
0.8
0
100
200 300
T, K
0
50 100 150 200 250 300
T, K
0
50 100 150 200
250 300
T, K
Fig. 3. Temperature dependence of the effective magnetic
moment of complex IVa.
Fig. 4. Temperature dependence of the effective magnetic
moment of complex IVb.
χ = χ'(1 – p) + [Nβ2g2S(S + 1)/3k(T – θ)]p.
is shorter than in IVb by 0.26 Å. Thus the EXAFS
spectra of copper complexes IVb and V confirmed
their dimeric structure.
Here, N, Nα, k, β, J, g, and θ are respectively the
Avogadro number, van Vleck paramagnetism,
Boltzmann constant, Bohr magneton, exchange
interaction parameter, Landé g-factor, and Weiss
constant. The calculated optimal parameters are given
below.
Magnetochemical studies revealed antiferro-
magnetic exchange interactions in complexes IV and
V. Figures 3–5 show the experimental and calculated
temperature dependences of the effective magnetic
moments and magnetic susceptibilities of complexes
IV and V. Assuming binuclear structure of the
complexes, the dependences were simulated using the
Bleany–Bowers equation for magnetic susceptibility of
the dimer [7]:
Comp. no.
IVа
1.92
–42
0.13
IVb
2.14
–9.7
0.22
V
g
2.11
–210
0.002
J, cm–1
p
Complexes IV are characterized by antiferro-
magnetic exchange [22] which is considerably stronger
in IVa (J = –42 cm–1) than in IVb (J = –9.7 cm–1). This
means that replacement of the donor group X in IVa
(X = O) by N-tosyl fragment (IVb, X = NTs)
considerably weakens antiferromagnetic exchange
interaction between the paramagnetic centers. Figure 5
shows that antiferromagnetic exchange between the
paramagnetic centers is also characteristic of metal
complex V. However, in the low-temperature region
(~20 K), the complex undergoes ferromagnetic phase
transition, and its unusual behavior attracts essential
interest.
χ(Cu–Cu) = (Nβ2g2/3kT)[1 + 1/3exp(–2J/kT)]–1 + Nα
with account taken of exchange interaction between
dimers zJ′:
χ(Cu–Cu)
1 – (2zJ'/Ng2β2)χ(Cu–Cu)
χ' =
and possible impurity p of monomeric species with a
spin S = 1/2:
Structural parameters determined by multisphere fitting of
the EXAFS spectra (R stands for interatomic distances, N is
the coordination number, σ2 is the Debye–Waller factor, and
Q is the goodness of fit function
EXPERIMENTAL
Comp. no.
N
R, Å
σ2, Å2
Atom
Q, %
The IR spectra were recorded on a Nicolet Impact-
400 instrument from samples dispersed in mineral oil.
The H NMR spectra were measured on a Varian
4
1
1.93
2.96
0.0035
0.0039
N
5.3
IVb
Cu
1
Unity-300 spectrometer at (300 MHz) using internal
5
1
1.94
2.70
0.0027
0.0037
O/N
Cu
2.7
V
stabilization with respect to 2H in CDCl3 or DMSO-d6.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 78 No. 6 2008

MOLECULAR DESIGN OF NEW MAGNETICALLY ACTIVE COPPER COMPLEXES
1233
χ, cm3mol–1
The CuK-edge X-ray absorption spectra were
recorded in the transmission mode on an EXAFS
spectrometer at the Structural Material Science Station,
Kurchatov Synchrotron Center (Moscow, Russia). The
energy of electron beam used as source of X-ray
synchrotron radiation was 2.5 GeV at a current of 80–
100 mA. The X-ray radiation was monochromatized
using a two-crystal Si(111) monochromator. The
spectra were processed by standard procedures for
background removal, normalization by the magnitude
of K-edge jump, and isolation of atomic absorption μ0
[23]; the EXAFS (χ) spectra were then subjected to
Fourier transform in the range of photoelectron wave
vectors k from 2.6 to 13 Å–1 with weight function k2.
The threshold ionization energy E0 was assumed to be
equal to the maximum of the first derivative of K-edge
and was then adjusted by fitting. The exact structural
parameters of the nearest environment of copper atoms
were determined by nonlinear fitting of parameters of
the corresponding coordination spheres via comparison
of the calculated EXAFS signal with that isolated from
the total EXAFS spectrum by filtration of the Fourier
transform. Nonlinear fitting was performed using
IFFEFIT-1.2.5 software package [24]. The photoelec-
tron scattering phases and amplitudes required for
simulation of the EXAFS spectrum were calculated
using FEFF7 program [25]; X-ray diffraction data for a
single crystal of bis[4-(5-chloro-2-hydroxyphenyl-
imino)pent-2-en-2-olato]dicopper(II) [21] (C22H20Cl2Cu2·
N2O4, TEKYIR [26]) were used as initial coordinates
of atoms for the calculation of scattering phases and
amplitudes and subsequent fitting. The goodness of fit
function Q was calculated by the formula
0.0012
0.0010
0.0008
0.0006
0.0004
0.0002
0.0000
0
50 100 150 200 250 300
T, K
Fig. 5. Temperature dependence of the specific magnetic
susceptibility of complex V.
aminopyridin-3-ol
with
2-hydroxybenzaldehyde.
Ligand III was synthesized as described for other azo
pyrazole derivatives [16, 28], by diazo coupling of o-
hydroxybenzenediazonium salt with 1-phenyl-3-
methyl-4,5-dihydro-1H-pyrazol-5-one.
2-{[(2-Hydroxyphenyl)methylidene]amino}pyri-
din-3-ol (II). Salicylaldehyde, 10 mmol, was added to
a solution of 10 mmol of 2-aminopyridin-3-ol in 50 ml
of ethanol, and the mixture was heated for 2 h under
reflux. After cooling, the precipitate was filtered off
and dried on exposure to air. Yellow–orange crystals,
mp 168–170°C (decomp.) IR spectrum, ν, cm–1: 3387
1
(OH), 1615 (C=N), 1274 (Ph–O). H NMR spectrum
(DMSO-d6), δ, ppm: 6.86–7.93 m (7H, Harom), 9.40 s
(1H, CH=N), 9.91 s (1H, OH), 13.69 s (1H, OH).
Found, %: C 67.38; H 4.61; N 13.18. C12H10N2O2.
Calculated, %: C 67.28; H 4.71; N 13.08.
Σ[kχexp(k) – kχth(k)]2
Q(%) =
×100%.
Σ[kχexp(k)]2
4-(2-Hydroxyphenylhydrazono)-3-methyl-1-phe-
nyl-4,5-dihydro-1H-pyrazol-5-one
(III).
Finely
powdered sodium nitrite, 22 mmol, was added in
portions to a solution of 20 mmol of o-aminophenol in
a mixture of 10 ml of acetic acid and 10 ml of
methanol under stirring at 10°C so that to avoid
evolution of nitrogen oxides. The mixture was kept on
cooling for 30 min, and 20 ml of water was added in
portions. The resulting diazonium salt solution was
slowly added under stirring to a mixture of 20 mmol of
3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one, 20 ml
of acetic acid, and 30 ml of methanol, the mixture was
kept for 10 h at room temperature and adjusted to pH
6–7 by adding a solution of sodium carbonate, and the
precipitate was filtered off, washed with 4–6 portions
of water, and dried in air. Yield 88%. mp 238–239°C
Minimization of
determining structural parameters of the nearest
environment of copper ions.
Q
was performed while
Magnetic properties of complexes IV and V were
studied on a Quantum Design SQUID magnetometer
in the temperature range from 300 to 2 K; magnetic
field strength 5 kOe. The effective magnetic moments
at different temperatures were calculated by the
formula
μef(T) = [(3k/Nβ2)χT]1/2 ≈ (8χT)1/2.
Schiff base II was synthesized according to the
procedure described in [22, 27] by reaction of 2-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 78 No. 6 2008

1234
BURLOV et al.
(from ethanol). IR spectrum, ν, cm–1: 3100 (N–H),
1660 (C=O), 1621 (C=N), 1233 (Ph–O). H NMR
> 250°C. IR spectrum, ν, cm–1: 1593 (C=N), 1300 (Ph–
O). Found, %: 54.14; 3.30; N 15.86.
1
C
H
spectrum (CDCl3), δ, ppm: 2.38 s (3H, CH3), 6.93–
7.97 m (9H, Harom), 12.25 s (1H, OH), 13.59 s (1H,
NH). Found, %: C 65.43; H 4.85; N 18.97.
C16H14N4O2. Calculated, %: C 65.30; H 4.79; N 19.03.
C32H12N4O2Cu2. Calculated, %: C 54.01; H 3.40; N
15.76.
Electrochemical syntheses of complexes IVa and
V were carried out according to the standard procedure
[32] by reaction of compound II or III, respectively,
with copper cations generated from the anode which
dissolved during the electrolysis. The electrochemical
cell may be represented as follows: Pt(–)/CH3CN//H2L
(II or III)/Cu(+). The acetonitrile solution (25 ml)
contained 1 mmol of ligand II or III and 0.01 g
Et4NClO4 as supporting electrolyte. The syntheses
were performed at a constant current of 40 mA and
voltage of 15 V; reaction time 2 h. The precipitate was
filtered off, washed with hot ethanol (3×10 ml), and
dried at 150°C under reduced pressure.
Complex IVa. Yield 68%. IR spectrum, ν, cm–1:
1606 (C=N), 1324 (Ph–O). Found, %: C 52.35; H
2.84; N 10.27.
Complex V. Yield 85%. IR spectrum, ν, cm–1: 1590
(C=N), 1290 (Ph–O). Found, %: C 54.15; H 3.28; N
15.85.
Copper complexes IV and V were synthesized by
direct reaction of copper(II) acetate with the
corresponding ligands, as well as by electrochemical
method (IVa, V) or template synthesis (IVb) [29–30].
Bis[2-{[2-hydroxyphenyl)methylidene]amino}pyri-
din-3-olato]dicopper(II) (IVa). A solution of 1 mmol
of copper(II) acetate monohydrate in 20 ml of ethanol
was added to a hot solution of 1 mmol of Schiff base II
in 50 ml of the same solvent, and the mixture was
heated for 4 h under reflux in an argon atmosphere..
After cooling, the precipitate was filtered off, washed
with hot ethanol (3×5 ml), and dried at 100°C under
reduced pressure. Yield 75%, brown powder, mp >
250°C. IR spectrum, ν, cm–1: 1605 (C=N), 1324 (Ph–
O). Found, %:
C
52.37; H 2.85;
N
10.27.
C24H16N4O4Cu2. Calculated, %: C 52.27; H 2.92; N
10.16.
Bis[2-{[(2-tosylaminophenyl)methylidene]amino}-
pyridin-3-olato]dicopper(II) (IVb). A solution of
1 mmol of 2-aminopyridin-3-ol in 20 ml of ethanol
was added to a hot solution of 1 mmol of 2-
tosylaminobenzaldehyde [31] in 30 ml of ethanol, and
the mixture was heated for 2 h under reflux in an argon
atmosphere. A solution of 1 mmol of copper(II) acetate
monohydrate in 20 ml of the same solvent was added,
and the mixture was heated under reflux for 2 h. The
mixture was cooled to room temperature, and the
precipitate was filtered off, washed with boiling
ethanol (3×5 ml), and dried at 150°C under reduced
pressure. Yield 70%, brown powder, mp > 250°C. IR
spectrum, ν, cm–1: 1608 (C=N), 1290 (νasSO2), 1090
(νsSO2). Found, %: C 53.25; H 3.61; N 9.76.
C38H30N6O6S2Cu2. Calculated, %: C 53.20; H 3.52; N
9.80.
ACKNOWLEDGMENTS
This study was performed under financial support
by the Presidium of the Russian Academy of Sciences
(program “Molecular Design of Magnetically Active
Substances and Materials”), by the Ministry of
Education and Science of the Russian Federation
(program “Development of Scientific Potential in
2006–2008,” project no. RNP.2.1.1.1875), by the
Russian Foundation for Basic Research (project nos.
07-03-00256, 07-03-00710, 08-03-00154), by the
President of the Russian Federation (program for
support of leading scientific schools, project no. NSh-
4849.2006.3), and by the Southern Federal University
(project no. 05/6-129).
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with hot methanol (3×10 ml), and dried at 150°C
under reduced pressure. Yield 90%, brown powder, mp
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