Polyhedron 29 (2010) 801806

Contents lists available at ScienceDirect

Polyhedron
journal homepage: www.elsevier.com/locate/poly

Syntheses and characterization of different zinc(II) oxide nano-structures

from direct thermal decomposition of 1D coordination polymers
Fahime Bigdeli a, Ali Morsali b,*, Pascal Retailleau c
a
Department of Chemistry, Payame Noor University, Abhar, Zanjan, Islamic Republic of Iran
b
Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14155-4838, Tehran, Islamic Republic of Iran
c
Service de Cristallochimie, Institut de Chimie des Substances Naturelles-CNRS, Bt 27, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France

a r t i c l e i n f o a b s t r a c t

Article history: Three zinc(II) nitrite coordination polymers, [Zn(4-bpdb)(NO2)2]n (1), {[Zn(3-bpdb)(NO2)]0.5H2O}n (2)
Received 31 May 2009 and [Zn(3-bpdh)(NO2)2]n (3), 4-bpdb = 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene, 3-bpdb = 1,4-bis(3-
Accepted 29 October 2009 pyridyl)-2,3-diaza-1,3-butadiene and 3-bpdh = 2,5-bis(3-pyridyl)-3,4-diaza-2,4-hexadiene} were pre-
Available online 4 November 2009
pared and characterized by elemental analyses and IR spectroscopy. Compound 3 was structurally char-
acterized by single-crystal X-ray diffraction and is one-dimensional polymer with coordination
Keywords: environments of distorted octahedral, ZnN2O4. The thermal stabilities of compounds 13 were studied
Zinc(II) oxide
by thermal gravimetric (TG) and differential thermal analyses (DTA). Direct calcination of the compounds
Nano-structure
Coordination polymer
13 at 600 C under air atmospheres yields different morphologies of nano-sized ZnO.
Zinc(II) nitrite 2009 Elsevier Ltd. All rights reserved.

1. Introduction ZnO is a polar inorganic crystalline material with many applica-

During the last two decades, the rational design and syntheses
of novel coordination polymers have made considerable progress
in the eld of supramolecular chemistry and crystal engineering
[16], not only because of the intriguing structural motifs of the
coordination polymers, but also because of their potential applica-
tions in catalysis, molecular adsorption, magnetism, nonlinear op-
tics, luminescence, and molecular sensing. In the design and
construction of these frameworks organic ligands play crucial roles
as even small changes in exibility, length, or symmetry of the li-
gands can result in a remarkable diversity of architectures and
functions [113].
The d10 metal ion Zn2+ is particularly suited for the construction
of coordination polymers and networks. The spherical d10 congu-
ration is associated with a exible coordination environment so
that geometries of these complexes can vary from tetrahedral to
octahedral and severe distortions in the ideal polyhedron occur
easily.
In this paper we describe the preparation of three zinc(II) nitrite
with ligands 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene (4-bpdb),
1,4-bis(3-pyridyl)-2,3-diaza-1,3-butadiene (3-bpdb) and 2,5-
bis(3-pyridyl)-3,4-diaza-2,4-hexadiene (3-bpdh) (Scheme 1),
[Zn(4-bpdb)(NO2)2]n (1) {[Zn(3-bpdb)(NO2)]0.5H2O}n (2) and
[Zn(3-bpdh)(NO2)2]n (3), and its use for preparation of different
morphologies of nano-sized ZnO.
* Corresponding author. Tel.: +98 9122420568; fax: +98 2188009730.
E-mail addresses: morsali_a@yahoo.com, morsali_a@modares.ac.ir (A. Morsali).
tions due to its unique combination of interesting properties such
as non-toxicity, good electrical, optical and piezoelectric behavior,
stability in a hydrogen plasma atmosphere and low price [1423].
ZnO is a well-known semiconductor with a wide direct band gap
(3.37 eV) and a large exciton binding energy of 60 meV at room
temperature [18,19] and it has a wide range of applications such
as solar cells, luminescent, electrical and acoustic devices, gas
and chemical sensors, coatings, catalysts, micro lasers, memory ar-
rays and biomedical applications [17,20]. Till now, many methods
have been developed to synthesize zinc oxide nanocrystals includ-
ing vapor phase growth [21], vaporliquidsolid process [15], soft
chemical method [23], electrophoretic deposition [24], solgel pro-
cess [25,26], homogeneous precipitation [27], etc. The use of orga-
nometallic supramolecular compounds as precursors for the
preparation of inorganic nano-materials such as zinc(II) oxide has
not yet been investigated thoroughly [2831].
The powders were characterized by means of powder X-ray dif-
fraction (XRD), scanning electron microscopy (SEM), IR spectros-
copy, thermal gravimetry analysis and differential thermal
analysis (TGA/DTA).
2. Experimental
2.1. Materials and physical techniques
With the exception of the ligands 4-bpdb, 3-bpdb and 3-bpdh
which were prepared according to the literature procedures [32
34], all reagents and solvents for the synthesis and analysis were

0277-5387/$ - see front matter 2009 Elsevier Ltd. All rights reserved.
doi:10.1016/j.poly.2009.10.027
802 F. Bigdeli et al. / Polyhedron 29 (2010) 801806

N
N N N N N N N
N N N
N

4-bpdb 3-bpdb 3-bpdh

Scheme 1. Flexible organic nitrogen donor-based ligands used in the construction of zinc(II) nitrite coordination polymer frameworks.

commercially available and used as received. IR spectra were re-
corded using PerkinElmer 597 and Nicolet 510P spectrophotome-
ters. Microanalyses were carried out using a Heraeus CHN-O-Rapid
analyzer. Melting points were measured on an Electrothermal
9100 apparatus and are uncorrected. X-ray powder diffraction
(XRD) measurements were performed using an Xpert diffractome-
ter of Philips Company with monochromatized Cu Ka radiation.
The crystallite sizes of selected samples were estimated using the
Scherrer method. TGA and DTA curves were recorded using a PL-
STA 1500 device manufactured by Thermal Sciences. The samples
were characterized with a scanning electron microscope (SEM)
(Philips XL 30) with gold coating. IR spectra were recorded on a
SHIMADZU-IR460 spectrometer in a KBr matrix.
Crystallographic measurements of compound 3 were made at
293(2) K using a Nonius kappa-CCD diffractometer. The intensity
data were collected within the range 2.56  h  27.48 using
graphite monochromated Mo Ka radiation (k = 0.71073 ). Accu-
rate unit cell parameters and orientation matrices were obtained
from least-squares renement. The structure has been solved by
direct methods and rened by full-matrix least-squares techniques
on F2. Crystallographic data and details of the data collection and
structure renement are listed in Table 1. The observed anisotropic
thermal parameters, the calculated structure factors, and full lists
of bond distances, bond angles and torsion angles are given in
the supplementary data. X-ray crystal structure is shown in Fig. 1.
2.2. Synthesis [Zn(4-bpdb)(NO2)2]n (1) and {[Zn(3-
bpdb)(NO2)]0.5H2O}n (2)
Compounds 12 were prepared using the reported method
[35].
Compound 1: reactant materials: 4-bpdb, Zn(CH3COO)2.2H2O,
NaNO2.
Product: yellow crystals, m.p. 283 C. (Anal. Calc. for
C12H10N6O4Zn: C, 39.23; H, 2.72; N, 22.88. Found: C, 39.50; H,
2.50; N, 22.55%). IR (cm1) selected bands: m = 666(s), 814(s),
1015(s), 1054(m), 1164(vs), 1264(vs), 1305(m), 1416(s), 1445(w),
1604(vs), 2923(w), and 3064(w).
Compound 2: reactant materials: 3-bpdb, Zn(CH3COO)2.2H2O,
NaNO2.
Product: yellow crystals, m.p. 185 C. (Anal. Calc. for
C24H22N12O9Zn2: C, 38.23; H, 2.92; N, 22.30. Found: C, 38.40; H,
2.50; N, 22.60%). IR (cm1) selected bands: m = 665(s), 862(m),
1023(s), 1044(m), 1185(vs), 1266(vs), 1307(m), 1415(vs),
1454(m), 1623(s), 2913(w), and 3042(w).

Table 1
2.3. Synthesis of [Zn(3-bpdh)(NO2)2]n (3)
Crystal data and structure renement for compound 1.

Identication code 1 To a magnetically stirred methanolic solution of 1 mmol

Empirical formula C14H14N6O4Zn
(0.214 g) Zn(CH3COO)22H2O was added dropwise a mixture of
Formula weight 395.68
Temperature 293(2)
1 mmol (0.230 g) of 2,5-bis(3-pyridyl)-3,4-diaza-2,4-hexadiene
Wavelength 0.71073 (4-bpdh) and 2 mmol (0.138 g) of NaNO2 in methanol and a little
Crystal system monoclinic water at room temperature over 30 min. The reaction mixture
Space group P21/c was stirred for 1 h at room temperature. Single crystals suitable
Unit cell dimensions
for X-ray analysis were obtained by slow evaporation of this solu-
a () 8.382(3)
b () 12.170(5) tion at room temperature (m.p > 320 C), which were ltered off,
c () 17.876(5) washed with acetone and dried in air. Yield: 0.198 g, 50%. Anal.
b () 116.98(2) Calc. for C14H14N6O4Zn: C, 42.45; H, 3.53; N, 21.23. Found: C,
Volume (3) 1625.0(10) 42.50; H, 3.50; N, 31.50%. IR (cm1) selected bonds: m = 630(m),
Z 4
Density (calculated) (g cm3) 1.617
721(m), 1262(s), 1382(M), 1624(m), 2040.
Absorption coefcient (mm1) 1.545
Crystal size (mm3) 0.32  0.24  0.18
h Range for data collection () 2.5627.48
3. Results and discussion
Index ranges 10  h  10
15  k  14 3.1. Synthesis and spectroscopy
23  l  23
Reections collected 16 861
Reaction between three exible organic nitrogen donor-based
Independent reections 3670
Absorption correction multi-scan ligands {4-bpdb, 3-bpdb and 3-bpdh} and mixtures of zinc(II) ace-
Max. and min. transmission 0.757 and 0.641 tate with sodium nitrite yielded crystalline materials formulated as
Renement method full-matrix [Zn(4-bpdb)(NO2)2]n (1), {[Zn(3-bpdb)(NO2)]0.5H2O}n (2) and
least-squares on F2 [Zn(3-bpdh)(NO2)2]n (3), respectively. The IR spectra display char-
Data/restraints/parameters 3670/0/228
Goodness-of-t (GOF) on F2 1.062
acteristic absorption bands for the ligands {4-bpdb, 3-bpdb and 3-
Final R indices [I > 2r(I)] R1 = 0.0398 bpdh} and the nitrite anions. The relatively weak absorption bands
wR2 = 0.0926 at around 3080 cm1 are due to the CH modes involving the aro-
R indices (all data) R1 = 0.0610 matic ring hydrogen atoms. The CH modes involving the aliphatic
wR2 = 0.1026
hydrogen atoms of ligands 4-bpdb, 3-bpdb and 3-bpdh in com-
Largest differences in peak and hole (e 3) 0.947 and 0.314
pounds 13 reveal around 2920 cm1. The absorption bands with
 F. Bigdeli et al. / Polyhedron 29 (2010) 801806 803

Fig. 1. (a) ORTEP diagram and showing a fragment of one-dimensional helix chain of compound 3, (b) showing the NHC and OHC weak hydrogen bonds and (c) schematic
representation of ZnII environment in the helix structure of compound 3. (i) x, y + 1/2, z + 1/2.

variable intensity in the frequency range 14001580 cm1 corre-
spond to ring vibrations of the py moiety of the ligands. The char-
acteristic bands of the nitrite groups appear at ca. 1174 and
1236 cm1. These values indicate that the nitrite anions coordinate
to the ZnII center in bidentate modes from only oxygen atoms [36].
3.2. Structure description
The structure of compounds 12 were previously analyzed and
reported [35] and are one-dimensional polymers with distorted
octahedral ZnN2O4 coordination environments with two N-donor
804 F. Bigdeli et al. / Polyhedron 29 (2010) 801806

ligands and the nitrite ligands being in cis-position to each other, 120 50
thus generating angular nodes of metal moieties and the structural
supramolecular isomers are of the 1D zigzag chain type. 100 40

Weight of loss(%)
Single X-ray crystal analysis reveals that compound 3 (Tables 1
80 30
and 2) crystallize in the monoclinic space group P21/c. Similar to

t(C)
the previously reported compounds 12, it also consists of one- TG
60 20
dimensional polymeric units of [Zn(3-bpdh)(NO2)2] (Fig. 1). The DTA
terminal nitrogen atoms of the 3-bpdh ligands are each linked to 40 10
two different zinc atoms, resulting in one-dimensional polymeric
20 0
units in the solid state. The coordination environments of the Zn
ions have very sever distorted octahedrons or similar to distorted 0 -10
trigonal prism (Fig. 1c) with the 3-bpdh ligands and the nitrite an- 0 200 400 600 800
ions, thus generating angular nodes at the metal moieties resulting
Temperature(C)
in 1D helix chains, which propagate around the glide planes.
In 3 there are also close intermolecular contacts between the Fig. 2. Thermal behavior of [Zn(l-4-bpdb)(NO2)2]n (1).
nitrogen atoms of the nitrite anions and the pyridyl hydrogen
atoms of neighboring molecules and the individual one-dimen-
sional units in 3 are almost parallel to each other and are further 120 30

Weight of loss(%)
linked by OHCmethyl and NHCpy interactions (Fig. 1b) with 100 25
OnitriteHC distances of 2.421 and 2.706 as well as with 80 20
TG

t(C)
NnitriteHC distances of 2.628 , resulting in a two-dimensional 15
60 10
framework (Fig. 1b). However, the structural determination of 40 DTA
5
compound 3 and its comparison with compounds 1 and 2 show 20 0
that the compounds are structurally similar featuring one-dimen- 0 -5
sional coordination but in contrast of zigzag chains in compounds 0 200 400 600 800
12 the compound 3 is helix type. This point underscores the sub- Temperature(C)
tle difference made by the displacement of hydrogen atoms of dia-
za group by methyl groups enabling the change from zigzag chain Fig. 3. Thermal behavior of {[Zn(3-bpdb)(NO2)]0.5H2O}n (2).
to helix type, probably due to strict effect of methyl groups.

3.3. Thermogravimetric analysis

In order to examine the thermal stability of the three com-

pounds, thermal gravimetric (TG) and differential thermal analyses
(DTA) were carried out for compounds 13 between 30 and 700 C
(Figs. 24).
The TG curve of compound 1 indicates that the compound does
not melt and is stable up to 240 C at which temperature it begins
to decompose (Fig. 2). Removal of the ligand 4-bpdb and decompo-
sition of the nitrite anions takes place in the range between 240
and 500 C with three exothermic effects at 245, 450 and 490 C,
ultimately giving a brown, amorphous solid that appears to be Fig. 4. Thermal behavior of [Zn(3-bpdh)(NO2)2]n (3).
ZnO (observed 21.70, calcd: 22.15%). Compound 2 is stable up to
125 C at which temperature the water molecule begins to be re-
brown, amorphous solid that appears to be ZnO (observed 21.70,
moved (Fig. 3). The solid residue formed at around 280 C is sug-
calcd: 21.50%).
gested to be the water-free compound, [Zn2(l-3-bpdb)2(NO2)4]n.
The TG curve of compound 3 indicates that the compound does
At higher temperatures, the release of the ligand 3-bpdb and the
not melt and is stable up to 240 C at which temperature it begins
decomposition of the nitrite anions occur to ultimately give a
to decompose (Fig. 4). Removal of the ligand 3-bpdh and decompo-
sition of the nitrite anions takes place in the range between 220
Table 2 and 500 C with three exothermic effects at 235, 370 and 490 C,
Selected bond lengths () and angles () for compound 1. ultimately giving a brown, amorphous solid that appears to be
Zn1O10 2.005(3) ZnO (observed 20.70, calcd: 20.47%).
Zn1N2 2.063(2)
Zn1N1 2.067(2) 3.4. Thermal decomposition of compounds 13
Zn1O30 2.170(3)
Zn1O40 2.318(3)
Zn1O20 2.710(3) Nano-structures of ZnO have been generated by thermal
O10 Zn1N2 119.76(10) decomposition of compounds 13. The nal product upon calcina-
O10 Zn1N1 113.40(10) tions of compounds 13 at 600 C, based on their IR, XRD patterns
N2Zn1N1 103.53(9) and TGA/DTA analyses, in three cases is ZnO.
O10 Zn1O30 92.18(11)
N2Zn1O30 133.47(11)
The IR spectrum of ZnO nanoparticles after calcination of com-
N1Zn1O30 91.58(10) pounds 13 shows the absorption bands at about 500 cm1 that
O10 Zn1O40 92.20(11) can be attributed to the stretching modes of ZnO and the weak
N2Zn1O40 89.37(10) bands in the range of 13803425 cm1 are probably attributed to
N1Zn1O40 138.70(10)
the presence of water in the KBr matrix. Fig. 5 shows X-ray powder
O30 Zn1O40 54.00(11)
diffraction pattern of ZnO nanoparticles after calcination of
 F. Bigdeli et al. / Polyhedron 29 (2010) 801806 805

Fig. 5. X-ray powder diffraction pattern of ZnO nanoparticles after calcination of compounds 13.

compounds 13. The XRD patterns for compounds 13 are quite
the same and are in agreement with the typical wurtzite structure
ZnO diffraction (hexagonal phase, space group P63mc, with lattice
constants a = 3.24982(9) , c = 1.6021 , Z = 2, JCPDS No. 36-
1451). Sharp diffraction peaks indicate good crystallinity of ZnO
nanoparticles. No characteristic peak related to any impurity was
observed. The broadening of the peaks indicated that the particles
were of nanometer scale which is in agreement with that observed
from SEM images (Figs. 68). For further demonstration, the EDAX
was performed for ZnO nanoparticles after calcination of com-

Fig. 6. SEM photographs of ZnO nanostructure (produced by calcinations of

compound 1). Fig. 8. SEM photographs of ZnO nanostructure (produced by calcinations of
compound 3).

Fig. 7. SEM photographs of ZnO nanostructure (produced by calcinations of

compound 2). Fig. 9. EDAX analysis of ZnO after calcination of compounds 13.
806 F. Bigdeli et al. / Polyhedron 29 (2010) 801806

110 30 Supplementary data

loss of weight(%)

100 20
CCDC 730691 contains the supplementary crystallographic data
90 10 for compound 3. These data can be obtained free of charge via

t(C)
TGA
80 0 http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the
DTA
70 -10 Cambridge Crystallographic Data Centre, 12 Union Road, Cam-
bridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail:
60 -20 deposit@ccdc.cam.ac.uk.
50 -30
0 200 400 600 800 Acknowledgements
Temperature(C)
This work was supported by the Payame Noor and Tarbiat Mod-
Fig. 10. TGDTA curves of the ZnO nanostructure after calcination of compounds ares Universities.
13.

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