Triclinic structural and magnetic properties of praseodymium(III) picrate triethylene glycol complex

Article abstract of DOI:10.1016/j.ica.2010.04.047

A study on the structure and magnetic properties of |Pr(NO ₃)(Pic)(H₂O)₂(EO3)](Pic) complex, where EO3 - triethylene glycol and Pic-picrate anion was conducted and characterized by single crystal X-ray structure analysis. Magnetic susceptibility χ/M) was carried out from 2 to 300 K under both field-cooled (FC) and zero-field-cooled (ZFC) measurements with an applied magnetic field of 2000 Oe. The complex is crystallized in triclinic with space group Pi. The coordination geometry around the Pr(IIl) ion was a tetradecahedron with a ten-coordination number. In the crystal, the molecular structure was stabilized by moderate and weak hydrogen bonding interactions between the cation [Pr(NO₃) (Pic)(H ₂O)₂(EO3)]₊ moiety and [Pic] as counter-anion that led to the formation of a one-dimensional network. The temperature dependence of the magnetic susceptibility of [Pr(NO ₃)(Pic)(H₂O)₂(EO3)](Pic) shows the presence of weak antiferromagnetic interactions between the Pr(III) centers. The magnetic susceptibility for complex also obeys the Curie-Weiss law and is effective at high temperatures. Some factors that influence the photoluminescence intensity were also reported.

Full text of DOI:10.1016/j.ica.2010.04.047

Inorganica Chimica Acta 363 (2010) 2533–2538
Contents lists available at ScienceDirect
Inorganica Chimica Acta
journal homepage: www.elsevier.com/locate/ica
Triclinic structural and magnetic properties of praseodymium(III) picrate
triethylene glycol complex
*
Eny Kusrini
Department of Chemical Engineering, Faculty of Engineering, University of Indonesia, 16424 Depok, Indonesia
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 22 June 2009
Received in revised form 9 April 2010
Accepted 16 April 2010
Available online 13 May 2010
A study on the structure and magnetic properties of [Pr(NO3)(Pic)(H2O)2(EO3)](Pic) complex, where
EO3 = triethylene glycol and Pic = picrate anion was conducted and characterized by single crystal
X-ray structure analysis. Magnetic susceptibility (vM) was carried out from 2 to 300 K under both
field-cooled (FC) and zero-field-cooled (ZFC) measurements with an applied magnetic field of 2000 Oe.
ꢀ
The complex is crystallized in triclinic with space group P1. The coordination geometry around the Pr(III)
ion was a tetradecahedron with a ten-coordination number. In the crystal, the molecular structure was
stabilized by moderate and weak hydrogen bonding interactions between the cation [Pr(NO3)
(Pic)(H2O)2(EO3)]+ moiety and [Pic]ꢀ as counter-anion that led to the formation of a one-dimensional net-
work. The temperature dependence of the magnetic susceptibility of [Pr(NO3)(Pic)(H2O)2(EO3)](Pic)
shows the presence of weak antiferromagnetic interactions between the Pr(III) centers. The magnetic
susceptibility for complex also obeys the Curie–Weiss law and is effective at high temperatures. Some
factors that influence the photoluminescence intensity were also reported.
Keywords:
Antiferromagnetic
Magnetic property
Picrate complex
Pr(III)
Triethylene glycol
Ó 2010 Elsevier B.V. All rights reserved.
1. Introduction
2. Experimental
Investigations on the Ln(III) complexes continue to be an active
research area due to the special and versatile physical properties of
these complexes and their possible applications as magnetic func-
tional materials [1–6] and electroluminescence devices [7–9]. Our
earlier findings of the antiferromagnetic Gd(III)–Gd(III) interac-
tions in the [Gd(Pic)2(H2O)(EO3)](Pic)ꢁCH3OH complex, where
EO3 = triethylene glycol and Pic = picrate anion, has been recently
reported [10]. The lanthanum analog was also observed and give
evidence as a diamagnetic ordering [10]. Its molecular structure
has been reported by Saleh et al. [11]. With the aim to support
our first result, we undertook the synthesis and magnetic studies
of Pr(III) complex with chelating EO3 and Pic ligands, varying the
donor strength, the number of oxygen donor atoms and/or the
coordination geometry around the central metal ion.
2.1. Materials
Triethylene glycol [C6H14O4, 99%] was purchased from Acros
(New Jersey, USA). Picric acid (Pic) [(NO2)3C6H2OH], >98% was pur-
chased from BDH (Poole, England). Pr(NO3)3ꢁ6H2O (99.9% purity)
was purchased from Johnson Matthey Electronics (New Jersey,
USA). Other chemicals were of analar grade and were used without
further purification.
2.2. Preparation of the Pr-EO3-Pic complex
The Pr-EO3-Pic complex was prepared by a procedure similar to
that of the Ln-EO3-Pic complexes as previously described [10–14].
To 0.434 g (1 mmol) of Pr(NO3)3ꢁ6H2O dissolved in 10 mL of aceto-
nitrile:methanol:water (3:3:1, v/v) was added 0.454 g of EO3
(3.0 mmol) and 0.917 g of HPic (4 mmol) previously dissolved in
20 mL of acetonitrile:methanol:water (3:3:1, v/v). The resulting
solution was stirred for 10 min at room temperature. The resultant
yellow solution was left covered to allow slow evaporation at room
temperature. After a few weeks, block shaped crystals started to
form. To obtain single-crystals suitable for X-ray diffraction, the
crystals was recrystallized in CH3OH, CH3CN, CH3OH:CH3CN (1:1,
v/v) and CH3OH solvents, respectively. The green single-crystal
was collected by filtration from the CH3OH solvent after one month
with 24% yield (0.43 g). Anal. Calc. C, 25.56; H, 2.60; N, 11.61.
We report herein the crystal structure, magnetic and lumines-
cence properties of the [Pr(NO3)(Pic)(H2O)2(EO3)](Pic) complex.
The magnetic susceptibility under both field-cooled (FC) and
zero-field-cooled (ZFC) measurements were investigated.
* Tel.: +62 21 7863516x6207; fax: +62 21 7863515.
E-mail address: ekusrini@che.ui.ac.id
0020-1693/$ - see front matter Ó 2010 Elsevier B.V. All rights reserved.
doi:10.1016/j.ica.2010.04.047

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E. Kusrini / Inorganica Chimica Acta 363 (2010) 2533–2538
Found: C, 25.24; H, 2.90; N, 12.09%. Decomposition point: 407.1–
463.4 K. IR (
/cmꢀ1): 3412(s), 1579(s), 1566(s), 1370(s), 1335(s),
1082(s), 1062(s), 1274(s), 1484(s), 813(w), 937(s), 795(s).
Data was collected after cooling in the absence of an applied field
(ZFC) and after cooling in a magnetic field (FC). No blocking or
freezing of magnetic moments was observed down to 2 K for the
complex studied. Measurements for determining the field depen-
dence of the magnetizations were also performed in an applied
field in the sequence of ꢀ5020 and +5020 Oe.
m
2.3. Physical measurements
Elemental analyses were performed by using a Perkin–Elmer
2400II elemental analyzer. IR spectrum was recorded on a Perkin–El-
mer 2000 FTIR spectrophotometer in the region of 4000–400 cmꢀ1
by using the KBr pellets for solid sample. For liquid sample i.e. EO3
ligand, a thin layer of sample was applied to the surface of a KRS-5
(thallium bromoiodide). Photoluminescence (PL) measurement
was performed at room temperature by using a Jobin Yvon HR800UV
system, the data collected and processed using Labspec Version 4
software source. A HeCd laser was used for excitation at 325 nm
and the emission spectra were scanned from 330 to 1000 nm.
2.5. X-ray crystallography analyses
X-ray diffraction data was collected from single crystal by using
a Bruker APEX2 CCD diffractometer with a graphite monochro-
matic Mo K
a radiation at a detector distance of 5 cm with APEX2
software [15]. The collected data were reduced by using SAINT pro-
gram and the empirical absorption corrections were performed
with the SADABS program [15]. The structure was solved by direct
methods and refined by least-squares using the SHELXTL software
package [16]. All non-hydrogen atoms were refined anisotropi-
cally. The hydrogen atoms in the carbon atoms were added from
theory calculation and the hydrogen atoms in the oxygen atoms
were added from Fourier maps and were isotropically refined.
The final refinement converged well. Data for publications were
prepared by using SHELXTL [16] and PLATON [17]. Crystal structure
and refinement data for compound is summarized in Table 1.
Selected bond lengths, bond angles and torsion angles are listed
in Table 2.
2.4. Magnetic susceptibility measurements
Magnetic susceptibility measurements on crystalline sample of
the complex (1 mg) were performed in the temperature range
2–300 K and an applied magnetic field 2000 Oe with a Supercon-
ducting Quantum Interference Device (SQUID) magnetometer.
Table 1
Crystallographic data and structure refinement for complex.
3. Results and discussion
Parameter
Compound
18H22N7O23Pr
845.34
1426.13(9)
Triclinic
Empirical formula
Molecular weight
Volume (Å3)
Crystal system
Space group
Z
C
3.1. Synthesis and physical properties
A small amount of water solvent in the mixture solution helped
the complex to form more readily compared to the solution with-
out water molecule. This method is recommended to add a small
amount of water in solution because of the small chain length of
the acyclic EO3 ligand [10–14,18]. The found and calculated per-
centages of elemental analyses are of good agreement with each
other and prove the suggested molecular formula of the complex.
The complex is also stable to air and moisture for a long-period
although it contains water molecules.
ꢀ
P1
2
Unit cell dimensions
a (Å)
7.141(3)
b (Å)
8.3219(3)
c (Å)
24.4799(9)
a
(°)
b (°)
(°)
Dcalc (g/cm3)
(mmꢀ1
F(0 0 0)
95.372(2)
91.092(2)
99.8220(10)
1.969
1.824
844
c
l
)
3.2. X-ray studies
Crystal size (mm)
h (°)
h, k, l
Reflections collected/unique
Refinement method
Data/restraint/parameter
Goodness-of-fit on F2
0.50 ꢂ 0.24 ꢂ 0.16
0.84–25.00
The asymmetric unit of the Pr(III) complex contains two crystal-
lographic independent [Pr(NO3)(Pic)(H2O)2(EO3)]+ and Pic counter
anion (Fig. 1a). The Pr(III) was coordinated to ten oxygen atoms
from one EO3 ligand, one picrate anion, one nitrate anion and
two water molecules. Coordination geometry around the Pr1 atom
is a tetradecahedron (Fig. 1b). The Pr(III) complex is crystallized in
ꢀ8/8, ꢀ9/9, ꢀ29/29
25817/4999 [Rint = 0.0261]
Full-matrix least-squares on F2
4999/0/442
1.082
Final R indices [I > 2
R indices (all data)
r(I)]
R1 = 0.0525, wR2 = 0.1538
R1 = 0.0529, wR2 = 0.1552
4.684 and ꢀ0.955
ꢀ
triclinic with space group P1. The [Pr(NO3)(Pic)(H2O)2(EO3)](Pic)
complex is isostructural similar to the two other cerium complexes
Largest difference in peak and hole (e Åꢀ3
)
Table 2
Selected bond length, bond angle and torsion angle for complex.
Atom
Length (Å)
Atom
Angle (°)
Atom
Torsion angle (°)
Pr1–O1
Pr1–O2
Pr1–O3
Pr1–O4
Pr1–O5
Pr1–O6
Pr1–O12
Pr1–O14
Pr1–OW1
Pr1–OW2
Average C–O
Average C–C
2.575(4)
2.569(4)
2.546(4)
2.509(4)
2.385(4)
2.606(4)
2.623(4)
2.622(4)
2.450(4)
2.569(4)
1.444(8)
1.480(9)
O1–Pr1–O2
O2–Pr1–O3
O3–Pr1–O4
O4–Pr1–O1
Average O–C–C
Average C–O–C
63.3(1)
62.5(1)
63.0(1)
141.4(1)
107.6(5)
114.8(5)
O1–C1–C2–O2
O2–C1–C2–O3
O3–C1–C2–O4
C2–O2–C3–C4
C3–O2–C2–C1
C4–O3–C5–C6
C5–O3–C4–C3
ꢀ52.9(8)
ꢀ55.5(6)
54.9(6)
ꢀ173.2(5)
ꢀ114.6(7)
167.9(5)
ꢀ167.3(5)

E. Kusrini / Inorganica Chimica Acta 363 (2010) 2533–2538
2535
Fig. 1. Molecular structure of [Pr(NO3)(Pic)(H2O)2(EO3)](Pic) with atom numbering of 50% ellipsoid probability (a) and coordination geometry around Pr1 atom (b). The
hydrogen atoms in carbon atoms are omitted for clarity.
[12] and [Eu(NO3)(Pic)(H2O)2(EO3)](Pic)ꢁH2O [13]. Molecular
structure of the complex reported here are unique when compared
to the [La(Pic)2(EO3)2](Pic) [11], [Gd(Pic)2(H2O)(EO3)](Pic)ꢁCH3OH
[10] and [Tb(Pic)2(H2O)(EO3)](Pic)ꢁ0.5(EO3) [14] complexes. One
nitrate anion from the starting material of [Pr(NO3)3ꢁ6H2O] salt
was still coordinated to the Pr(III) ion in a bidentate mode and
helped to stabilize the complex. The water molecule was also
involved in the inner-coordination sphere of the Pr(III) complex
because lacking of the donor oxygen atoms from the EO3 ligand
to form a complex. A coordination number in the complex studied
is similar with the Ce(III) and Eu(III) analog complexes [12,13].
However, we evaluate the heavier lanthanide analog complexes
for Gd [10] and Tb [14] that led to the forming a nine coordination
number. This is due to the lanthanide contraction effect, the acyclic
polyether chain length and number of donor oxygen atoms. For
comparison purpose, the [Pr(NO3)3(EO3)] complex showed a ten-
coordination number without the presence of second bulky Pic
anion for charge balancing to the central metal ion. In this case,
the Pr(III) ion was coordinated to the EO3 ligand and completed
with three nitrate anions [19].
in the cerium analog complex [12]. However, these bond length
are larger than those found in the Gd(III) [10], Eu(III) [13] and
Tb(III) [14] analog complexes. Bond angle for O1–Pr–O4 between
Table 3
Hydrogen bonding in the complex.
D–Hꢁ ꢁ ꢁA
D–H (Å)
Hꢁ ꢁ ꢁA (Å)
Dꢁ ꢁ ꢁA (Å)
D–Hꢁ ꢁ ꢁA (°)
O4–H1Cꢁ ꢁ ꢁO12i
0.819
0.819
0.851
0.851
0.851
0.851
0.851
0.850
0.970
0.970
0.971
0.970
0.970
0.971
0.969
1.983
2.410
1.951
2.252
2.425
2.248
2.596
2.140
2.529
2.535
2.507
2.542
2.409
2.576
2.404
2.781(6)
2.816(6)
2.646(6)
2.942(7)
2.769(6)
3.083(6)
3.044(6)
2.763(6)
3.423(9)
3.173(7)
3.445(7)
3.419(7)
3.225(7)
3.118(7)
3.373(8)
164.5
111.5
138.2
138.3
104.9
166.9
114.1
130.0
153.3
123.4
162.6
150.4
141.5
115.3
177.8
O1–H4Cꢁ ꢁ ꢁO19ii
O1W–H11Wꢁ ꢁ ꢁO15
O1W–H11Wꢁ ꢁ ꢁO21
O2W–H12Wꢁ ꢁ ꢁO15
O2W–H12Wꢁ ꢁ ꢁO16
O2W–H12Wꢁ ꢁ ꢁO20iii
O1W–H21Wꢁ ꢁ ꢁO14iv
C2–H2Aꢁ ꢁ ꢁO18v
C3–H3Bꢁ ꢁ ꢁO13iii
C4–H4Aꢁ ꢁ ꢁO6b
C4–H4Bꢁ ꢁ ꢁO11iii
C5–H5Aꢁ ꢁ ꢁO14iv
C5–H5Bꢁ ꢁ ꢁO5b
C6–H6Aꢁ ꢁ ꢁO6i
The average Pr–Oalcohol, Pr–Ophenol, Pr–Oether, Pr–Onitro and
Pr–Onitrato bond lengths are 2.542(4), 2.385(4), 2.558(2), 2.606(4)
and 2.623(4) Å, respectively. These bond lengths are slightly
smaller relative to those found in the average Ce–O bond lengths
aSymmetry codes: (i) 1 + x, y, z; (ii) 1 ꢀ x, 1 ꢀ y, 1 ꢀ z; (iii) x, 1 + y, z; (iv) 1 + x, 1 + y,
z; (v) 1 ꢀ x, 2 ꢀ y, 1 ꢀ z.
bIntramolecular hydrogen bonding.

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E. Kusrini / Inorganica Chimica Acta 363 (2010) 2533–2538
the oxygen of the terminal alcohol groups was 141.4(1)°. Thus, the
inner-coordination sphere of the complex is opened and pseudo-
cyclic conformation was adopted. The O–C–C–O torsion angles
from the ring of the EO3 ligand use the conformation patterns of
gꢀ gꢀ g+. All the C–O–C–C torsion angles are anti, except C3–O2–
C2–C1 is close to the gauche conformation (gꢀ). The coordinated
picrato O5/C7/C8/O6 (maximum deviation 0.352(4) Å at the O6
atom) and nitrato O12/N4/O13/O14 fragments are planar with
the Pr1 atom displaced by 0.559(1) and ꢀ0.162(1) Å from both
fragments, respectively. Both fragments are inclined toward each
other by dihedral angle of about 84.3(3)° (Fig. 1a).
for the FC and ZFC data, respectively. The vMT values decrease in
the lower temperature region because of the saturation effects
and the crystal field effects as well [2]. This is in agreement with
the weak intermolecular interactions as expected from the crystal
structure studies which shows well synthesized [Pr(NO3)(Pi-
c)(H2O)2(EO3)]+ unit. From the structure of cations, the short dis-
tances between Prꢁ ꢁ ꢁPr is 7.141 Å (see Fig. 2). Thus, the Pr
complex is mononuclear with slightly antiferromagnetic exchange
interactions between the Pr(III) centers.
1
At least-squares analysis of the
vs. T curve yields the Currie
vM
constant C = 1.80 ꢂ 104 emu K molꢀ1 and h = ꢀ0.68 K, indicating a
The crystal structure of the complex is stabilized by intra- and
intermolecular hydrogen bonds that led to the forming a one-
dimensional layer with symmetry direction [1 0 0] (Table 3 and
Fig. 2). Short Oꢁ ꢁ ꢁO and Nꢁ ꢁ ꢁO contact between the nitro groups,
intramolecular C–Hꢁ ꢁ ꢁO, intermolecular O–Hꢁ ꢁ ꢁO and C–Hꢁ ꢁ ꢁO
weak antiferromagnetic coupling as confirmed by the
vMT curve,
which decrease on lowering the temperature. Both FC and ZFC data
follow the Curie–Weiss law and is effective at high temperatures
1
between 170 and 300 K in the equation,
¼
Tꢀh. The linear depen-
vM
C
1
dence of
at high temperatures is consistent with independence
vM
hydrogen bonds, and two p–p interactions between aromatic rings
spins, it extrapolates to negative Weiss h value for complex indicat-
ing that the dominant antiferromagnetic interactions are operative
between the Pr(III) centers. The small negative Weiss constant (h)
also suggests a weak antiferromagnetic interactions between the
metal ions [1,20].
in face to face modes [centroid–centroid distances = 4.024(4)–
4.402(3) Å] are observed.
3.3. Magnetic susceptibility
The field dependence of magnetizations measured at 2, 20 and
300 K and in the range ꢀ5020 to +5020 Oe and reached maximum
values of 1.18 ꢂ 102, 3.57 ꢂ 102 and 6.09 ꢂ 102 lB at 5020 Oe
(Fig. 4). The field dependence of the magnetization for complex re-
corded at 2, 20 and 300 K reveal hysteresis curve with coercive
filed (Hc) of 13, 12.5 and 38 Oe and remnant magnetization of
Magnetic susceptibility of this complex is investigated from 2 to
300 K at 2000 Oe and exhibits similar behavior throughout the
temperature range studied for both FC and ZFC measurements.
The Pr(III) complex shows a small divergence between the FC
and ZFC data near 12.2 K. The temperature dependence of the FC
4.67, 12.98 and 53.58
lB, respectively. Magnetic hysteresis is an
and ZFC magnetizations showed
a decrease gradually from
important phenomenon and refers to the irreversibility of the mag-
netization and demagnetization process. In this region the magne-
tization curve is irreversible. The field dependence of the
magnetization recorded at 2, 20 and 300 K suggested that the com-
plex reach saturation magnetization of 5.31, 16.56 and 127.87 lB
and in applied field at 99.5, 99.5 and 199.0 Oe. It was also observed
that the saturation magnetization decreases with increasing tem-
perature until it falls to 0.0715 emu gꢀ1 at 300 K.
3.81 ꢂ 102
l
B at 300 K to reach about 3.43 ꢂ 102
lB at 101 K. Below
this temperature, the magnetization abrupt rise with values of 72.9
and 73.1
lB at 2 K for FC and ZFC measurements, respectively. The
experimental effective magnetic moment (
room temperature, which is larger than those found in the corre-
l
eff) is 3.81 ꢂ 102 lB at
sponding of free Pr(III) ion (2.832 lB). The other possibility is due
to the presence of water molecules in the formation of complex.
The theoretical value of leff for the free Pr(III) ion was calculated
from S = 1 (2/2, two unpaired electron) and g = 2.0023.
Fig. 3 shows a the
v
MT value of 1.81 ꢂ 104 emu K molꢀ1 at 300 K
3.4. Photoluminescence (PL) studies
and decreases gradually to reach of 1.63 ꢂ 104 emu K molꢀ1 at
141 K, where
vM = magnetic susceptibility. Upon cooling, the
vMT
The emission spectra of the free EO3, HPic ligands and its com-
plex were evaluated in the solid state at room temperature based
on D2 filter measurement. The complex had broad emission peak
values decreases continuously and are faster. At low temperature
(2 K), the
v
MT values are 6.64 ꢂ 102 and 6.70 ꢂ 102 emu K molꢀ1
Fig. 2. A viewed crystal packing of complex along b-axis. Dashed (- - -) lines represent the O–Hꢁ ꢁ ꢁO and C–Hꢁ ꢁ ꢁO hydrogen bonding.

E. Kusrini / Inorganica Chimica Acta 363 (2010) 2533–2538
2537
2.00E+04
1.60E+04
1.20E+04
8.00E+03
4.00E+03
0.00E+00
FC
ZFC
0
50
100
150
200
250
300
T (K)
Fig. 3. Temperature dependence of magnetic susceptibility for complex.
6.00E+02
4.50E+02
3.00E+02
1.50E+02
0.00E+00
2K
20K
300K
0
1000
2000
3000
4000
5000
H
(Oe)
Fig. 4. Magnetic field dependence of the magnetization recorded at 2, 20 and 300 K for complex.
in the range 450–680 nm with the center peak at 537.2 nm and its
Acknowledgements
intensity about 869 ꢂ 102 a.u. The red-shift emission peak from
complex is compared to the EO3 ligand, probably due to the in-
tra-ligand phosphorescence emission [21,22]. It is noted that the
Pic anion and water molecules act a quencher in the complex.
The electron-withdrawing nitro (NO2) and hydroxyl (OH) groups
This study was supported by University of Indonesia. The mag-
netic susceptibility was performed at Department of Materials Sci-
ence and Engineering, National Chiao Tung University, Hsin Chu,
Taiwan. We deeply appreciate the assistance of Dato’ Prof. Muham-
mad Idiris Saleh and Prof. Bahruddin Saad (School of Chemical Sci-
ences, Universiti Sains Malaysia, Penang) and Prof. Dr. Yung-Jung
Hsu (Department of Materials Science and Engineering, National
Chiao Tung University, Hsin Chu, Taiwan) for a valuable discussion
and their encouragements.
in the Pic anion also influence the distribution of
density.
p-electronic
4. Conclusion
The single-crystals of [Pr(NO3)(Pic)(H2O)2(EO3)](Pic) complex
was successfully prepared. The EO3 ligand is able to bound the
Pr(III) ion in a pseudo-cyclic conformation in a ten-coordination
number. Both FC and ZFC data show very similar magnetic behav-
ior in the antiferromagnetic ordering. The fitting to the Curie–
Weiss law for the complex indicates that the effective magnetic
moment is significantly larger than those of the corresponding free
Pr(III) ion.
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