A new 3D supramolecular array assembled by leftand righthanded helical Ni(II) coordination polymer chains based on 3,5-dinitrobenzoate and a flexible double imidazole derivative

Article abstract of DOI:10.1134/S0036023611120382

A new nickel(II) coordination polymer with leftand right-handed helical chains [Ni(dmbbbi)(DNBA)₂(H₂O)] (1) has been obtained from hydrothermal reaction of nickel(II) nitrate with a flexible double imidazole derivative 1,1-(1,4-butanediyl)bis(5,6-dimethylbenzimidazole) (dmbbbi) and 3,5dinitrobenzoic acid (HDNBA). Single-crystal X-ray diffraction analysis reveals that the crystal is triclinic: a = 9.821(5) ?, b = 13.084(5) ?, c = 14.705(5) ?, α = 105.249(5)°, β = 95.688(5)°, γ = 94.273(5)°, Z = 2, V = 1804.1(13) ?3, ρ_calc = 1.553 mg/m³, GOOF = 1.064, the final R = 0.0360 and wR = 0.0999. The crystal structure analysis indicates that the nickel atom is six coordinated by three oxygen atoms from two DNBA with two kinds of coordination modes, two nitrogen atoms from different dmbbbi and a coordination water molecule forming a [NiN₂O₄] subunit. The subunits are linked by dmbbbi to form a one dimensional (1D) helical coordination polymer chain and the adjacent chains are further connected by hydrogen bonding interactions to form a novel leftand right-handed helical double-chain structure. The double-chains are ultimately extended into 3D supramolecular structure through π-π stacking interactions. Moreover, thermal stability of title compound and the cyclic voltammetry behavior of compound 1 modified carbon paste electrode (1-CPE) in 1 M H₂SO₄ solution are investigated. Pleiades Publishing, Ltd., 2011.

Full text of DOI:10.1134/S0036023611120382

ISSN 0036ꢀ0236, Russian Journal of Inorganic Chemistry, 2011, Vol. 56, No. 12, pp. 1918–1923. © Pleiades Publishing, Ltd., 2011.
COORDINATION COMPOUNDS
A New 3D Supramolecular Array Assembled by Leftꢀ and Rightꢀ
Handed Helical Ni(II) Coordination Polymer Chains Based
on 3,5ꢀDinitrobenzoate and a Flexible Double Imidazole Derivative1
G. C. Liu, S. Yang, X. L. Wang, Y. F. Wang, H. Y. Lin, and J. X. Zhang
Faculty of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121000, P. R. China
eꢀmail: wangxiuli@bhu.edu.cn
Received July 28, 2010
Abstract—A new nickel(II) coordination polymer with leftꢀ and rightꢀhanded helical chains
[Ni(dmbbbi)(DNBA)2(H2O)] (1) has been obtained from hydrothermal reaction of nickel(II) nitrate with a
flexible double imidazole derivative 1,1ꢀ(1,4ꢀbutanediyl)bis(5,6ꢀdimethylbenzimidazole) (dmbbbi) and 3,5ꢀ
dinitrobenzoic acid (HDNBA). Singleꢀcrystal Xꢀray diffraction analysis reveals that the crystal is triclinic:
= 9.821(5) = 13.084(5) = 14.705(5) = 105.249(5) = 95.688(5) = 94.273(5) = 2,
= 1804.1(13) Å3 calc = 1.553 mg/m3, GOOF = 1.064, the final
= 0.0360 and wR = 0.0999. The crystal
a
V
Å,
b
Å,
c
Å,
α
°
R
,
β
°,
γ
°, Z
,
ρ
structure analysis indicates that the nickel atom is six coordinated by three oxygen atoms from two DNBA
with two kinds of coordination modes, two nitrogen atoms from different dmbbbi and a coordination water
molecule forming a [NiN2O4] subunit. The subunits are linked by dmbbbi to form a one dimensional (1D)
helical coordination polymer chain and the adjacent chains are further connected by hydrogen bonding interꢀ
actions to form a novel leftꢀ and rightꢀhanded helical doubleꢀchain structure. The doubleꢀchains are ultiꢀ
mately extended into 3D supramolecular structure through
stability of title compound and the cyclic voltammetry behavior of compound
trode ( ꢀCPE) in 1 M H2SO4 solution are investigated.
π
–
π
stacking interactions. Moreover, thermal
1
modified carbon paste elecꢀ
1
DOI: 10.1134/S0036023611120382
1
Helical structures, the foundation of the genetic as the supramolecular recognition sites may induce the
code, have received much attention in coordination
chemistry and materials chemistry over the past
decade, because helicity is an essential ellement of life
and is also important in advanced materials such as
biomimetic chemistry and asymmetric catalysis [1, 2].
Many chemists have made great contributions to this
field and some singleꢀ, doubleꢀand multiꢀstranded
helical metalꢀorganic coordination polymer have been
metalꢀorganic coordination polymer to form multiꢀ
stranded helix [4].
On the basis of the aforementioned points, we
chose 1,1ꢀ(1,4ꢀbutanediyl)bis(5,6ꢀdimethylbenzimiꢀ
dazole) (dmbbbi) and 3,5ꢀdinitrobenzoic acid
(HDNBA) as the mixed ligands because of their
remarkable advantages: (i) Comparing to double imiꢀ
obtained by selfꢀassembly processes [3, 4]. However, dazole derivative ligands, dmbbbi not only possesses
one of the obvious challenges to chemists is the ratioꢀ
nal and controllable preparation of the target metal
organic compound in this area [5], the formation of
which is greatly affected by the ligand nature, counteꢀ
rions and other factors [6–9]. As an important family
of multidentate Nꢀdonor ligands, double imidazole
groups modified aromatic and fatty hydrocarbon as
bridging ligand seem to be excellent building block
with versatile coordination modes as well as the
remarkable coordination ability and stability [10, 11].
On the other hand, noncovalent supramolecular interꢀ
muiti –CH2– groups for freely twisty, but also has the
larger aromaticꢀring system and may provide potential
supramolecular recognition sites for
π
–
π
stacking
interactions, (ii) As a multifunctional Oꢀdonor ligand,
DNBA has remarkable coordination ability and many
potential Hꢀbonding acceptors to extend the helical
structure constructed by dmbbbi ligands and metal
cations. Fortunately, a novel nickel(II) coordination
polymer with leftꢀ and rightꢀhanded helical chains
[Ni(dmbbbi)(DNBA)2(H2O)] (1) has been obtained
from hydrothermal reaction and the elemental analyꢀ
sis, IR spectrum, thermal stable and electrochemistry
properties of title compound are studied in this report.
actions (hydrogen bonds,
π
– stacking interactions)
π
1
The article is published in the original.
1918

A NEW 3D SUPRAMOLECULAR ARRAY
N
1919
Ni
N
2
N
N
O
N
C
O4
Ni1
N4
O2
dmbbbi
(a)
N1
O1
O3
O2N
NO2 O2N
NO2
C
C
Fig. 1. View of the coordination environment of Ni atom
in compound 1.
O
O
O
O
Ni
DNBAb
Ni
DNBAa
(b)
(a)
Scheme 1. (a) The Nꢀligand used in this report; (b) monoꢀ
dentate (left) and chelating (right) coordination modes of
DNBA.
L
b
a
O2
O1
O2
O1
O2
O2
O1
O1
O2
O1
O2
c
O1
O2
O1
O1
EXPRIMENTAL
O2
All chemicals purchased were of reagent grade and
used without further purification, dmbbbi was syntheꢀ
sized by the method of the literature [12] and characꢀ
terized by 1H NMR spectrometer analyses and FTꢀIR
spectra. 1H NMR analyses were performed on a Varian
(b)
Mercury V
×
300 spectrometer Analyzer and FTꢀIR
spectra (KBr pellets) were taken on a Magna FTꢀIR
560 spectrometer. A CHI 440 Electrochemical Quartz
Crystal Microbalance was used for the electrochemiꢀ
cal experiments and elemental analyses (C, H and N)
were performed on a PerkinꢀElmer 240C analyzer.
Thermogravimetric data for the title compound was
collected on a Pyris Diamond thermal analyzer.
Synthesis of [Ni(dmbbbi)(DNBA)2(H2O)] (1)
mixture of Ni(NO3)2 4H2O (0.1 mmol), dmbbbi
(0.1 mmol), HDNBA (0.2 mmol), NaOH (0.2 mmol),
H2O (10 mL), stirred for 20 min, was sealed to a
Teflonꢀlined stainless steel autoclave (25 mL) and kept
. A
c
b
a
⋅
(c)
at 150
cooled to room temperature, green block crystals suitꢀ
able for Xꢀray diffraction of were isolated by
°C for 3 days. After the mixture was slowly
1
mechanical separation from a green amorphous solid
in 42% yield (based on NiII salt).
For C36H34N8NiO13 anal. calcd. (%): C, 51.14; H,
4.05; N, 13.25.
Found (%): C, 51.18; H, 4.02; N, 13.21.
1
IR (KBr)
(
ν
, cm– ): 3400 w, 3105 m, 2943 m, 1658 s,
Fig. 2. (a) View of the 1D doubleꢀchain structure conꢀ
structed by single handed helical chains through hydrogen
bonding interactions between coordination water moleꢀ
cules (O1) and carboxyl groups (O2) (dotted blue lines),
DNBA were omitted for clarity; (b) view of 2D supramoꢀ
1618 s, 1581 m, 1537 s, 1454 m, 1386 m, 1344 s, 1205 m,
1074 m, 916 m, 727 s.
Preparation of complex 1 modified carbon paste
electrode. The modified carbon paste electrode
lecular network extended by the
π
– stacking interactions
π
(1ꢀCPE) was fabricated as follows: 0.50 g graphite
between the aromatic rings of dmbbbi (dotted sky blue
powder and 0.030 g compound
1 were mixed and
a
lines); (c) view of the
with a monoꢀdentate coordination mode (dotted pink
lines) in compound
π
–
π
stacking interactions of DNBA
ground together by agate mortar and pestle for approxꢀ
imately 20 min to achieve an even, dry mixture; to the
1
.
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 56 No. 12 2011

1920
LIU et al.
Table 1. Crystal data and structure refinement for complex
1
Table 2. Selected bond lengths (
d
) and bond angles (
, Å
ω
) for
complex
1
Formula wt.
Crystal system
Space group
845.42
Triclinic
P1
Bond
d
Ni(1)–N(1)
Ni(1)–O(1)
Ni(1)–O(2)
Ni(1)–O(4)
Ni(1)–N(4)#1
Ni(1)–O(3)
Angle
2.0641(19)
2.087(2)
a
b
(Å)
(Å)
(Å)
9.821(5)
13.084(5)
14.705(5)
105.249(5)
95.688(5)
94.273(5)
1804.1(13)
2
2.1185(17)
2.0522(16)
2.0989(19)
2.2267(17)
c
α
β
γ
(°
)
(
°)
(°)
(Å3)
ω
, deg
V
Z
O(4)Ni(1)N(1)
N(1)Ni(1)O(1)
92.75(7)
86.62(8)
96.64(7)
104.04(6)
88.80(7)
164.08(6)
86.64(7)
89.04(8)
93.32(7)
175.87(7)
162.51(7)
87.34(7)
102.28(6)
90.18(6)
60.58(5)
D
μ
F
(g cm–3)
(mm–1)
(000)
1.553
N(1)Ni(1)N(4)#1
O(4)Ni(1)O(2)
0.619
872
O(1)Ni(1)O(2)
θmax (deg)
2.45–25.00
O(4)Ni(1)O(3)
Index ranges
–11
–15
–17
≤
≤
≤
h
k
l
≤
11
15
17
≤
O(1)Ni(1)O(3)
≤
O(4)Ni(1)O(1)
Reflections collected
Unique reflections
Rint
14350
6325
O(4)Ni(1)N(4)#1
O(1)Ni(1)N(4)#1
N(1)Ni(1)O(2)
0.0161
0.0360
Ra
[I
> 2σ(I
)]
N(4)#1Ni(1)O(2)
N(1)Ni(1)O(3)
1
b
0.0999
w
(all data)
R2
GOOF on F 2
Δρmax (e Å–3)
Δρmin (e Å–3)
1.064
1.047
N(4)#1Ni(1)O(3)
O(2)Ni(1)O(3)
Note: Symmetry codes: #1 x – 1, y, z.
–0.744
ses. The final
R
= 0.0360 and wR = 0.0999 (
w
=
+
mixture 0.15 mL paraffin oil was added and stirred
with a glass rod; then the homogenized mixture was
used to pack 3 mm inner diameter glass tubes to a
length of 0.7 cm, the surface of the modified CPE was
wiped with weighing paper, and the electrical contact
was established with the copper stick. The same proceꢀ
dure was used for preparation of bare CPE without Ni
complex [13].
2
1/[
σ
(
2) + (0.0536
P
)2 + 1.1179
P], where
P
= (
2
Fo
Fo
2
2)/3;
S
= 1.064. The crystal data and structure
are given in Table 1. Selected
Fc
refinement details for
1
bond lengths and angles are listed in Table 2. Crystalꢀ
lographic data for the structure reported in this paper
has been deposited in the Cambridge Crystallographic
Data Center with CCDC reference number 783731.
Xꢀray crystallography. A green single crystal with
dimensions of 0.22 mm
×
0.28 mm
×
0.36 mm was
RESULTS AND DISCUSSION
selected for Xꢀray structure analysis. Data were colꢀ
lected on a Bruker Smart Apex II CCD diffractometer
Singleꢀcrystal Xꢀray analysis shows that compound
is a 3D supramolecular network derived from 1D leftꢀ
and rightꢀhanded helical chains extended by hydrogen
1
with Mo
K
(
λ
= 0.71073
Å)
at 293 K by using an
ω
–2
θ
α
scan mode. 5867 reflections were used in the succeedꢀ
ing refinement. The structures were solved by the
direct method and refined by the Fullꢀmatrix leastꢀ
bond and
π
ꢀ
π
stacking interactions. The crystal strucꢀ
ture analysis indicates that the nickel atom is six coorꢀ
squares on F2 using the SHELXLꢀ97 software [14, 15]. dinated with three oxygen atoms from different
All the nonꢀhydrogen atoms were refined anisotropiꢀ DNBA [Ni–O 2.1185(17), 2.2267(17) Å], two nitroꢀ
cally. The hydrogen atoms of the ligands were generꢀ gen atoms with a cis coordination mode from different
ated theoretically onto the specific atoms and the dmbbbi [Ni–N 2.0641(19)–2.0989(19) Å] and a oxyꢀ
hydrogen atoms of the coordination water molecule gen atom from coordination water molecule [Ni–O
were located in successive difference Fourier syntheꢀ 2.087(2) Å] showing a octahedral coordination geomꢀ
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 56 No. 12 2011

A NEW 3D SUPRAMOLECULAR ARRAY
1921
etry (Fig. 1). The Ni octahedron is slightly distorted,
(a)
which may be caused by the steric effects of the
ligands.
It is worth mentioning that the Ni atoms are linked
by dmbbbi to form a 1D helical coordination polymer
due to the twisty configuration of the dmbbbi, with a
Ni⋅⋅⋅Ni separation of 9.821 Å and the dihedral angel of
the aromatic rings from dmbbbi is 73.08 . Furtherꢀ
°
more, the adjacent single handed helical chains are
connected by hydrogen bond interactions between the
coordination water molecules and chelating carboxyꢀ
late oxygen atoms to form a interesting leftꢀand rightꢀ
handed helical doubleꢀchain structure [O(1)–
b
a
c
H(1A)⋅⋅⋅O(2), 2.801(3)
ble chains are extended into 2D supramolecular layer
through stacking interactions between the aroꢀ
Å, 160(4)
°
] (Fig. 2a). The douꢀ
π π
–
(b)
matic rings of dmbbbi (Fig. 2b). The Cg–Cg (Disꢀ
tance between ring Centroids) distance between benꢀ
zyl ring and the imidazole ring of dmbbbi ligands from
the adjacent double chains is 3.651(2) Å, and the diheꢀ
dral angels is 1.17
°
. The adjacent layers are ultimately
extended into a 3D supramolecular network by
π π
–
stacking interactions between the aromatic rings of
DNBAa with the monoꢀdentate coordination mode
[Cg–Cg is 3.653(2) Å, and the dihedral angels is
(Fig. 2c).
0°]
To best understand the structure of compound 1, it
is necessary to simplify the building blocks from the
3D supramolecular network. Considering the binuꢀ
clear Ni cluster linked by hydrogen bonds as a six conꢀ
nected node, the two dmbbbi as the covalent double
spacers and the two kinds of supramolecular actions as
b
c
the nonꢀcovalent spacers, the whole structure of
1
can
be considered to be a distorted
(Figs. 2b, 2c, 3) [16].
aꢀPo topology network
To our knowledge, three kinds of interactions are
unusually used to link the leftꢀ and rightꢀhanded heliꢀ
cal metalꢀorganic coordination polymer chains,
Fig. 3. (a) aꢀPo network of compound 1; (b) view of the
arrangement of the 3D supramolecular network.
namely: covalence bond,
π
– stacking interaction and
π
hydrogen bond. For example, Du and coworkers have
obtained a series of doubleꢀstrand helical chains
100
80
60
40
20
0
[M(pya)2(H2O)2] (M = Cu, Co, Ni, pya = 4ꢀpyridylꢀ
acetic acid) extended by covalence bonds [17]. Chen
and coworkers have obtained the first zipperꢀlike douꢀ
bleꢀstrand helical chain [Cu2(ipa)2(phen)2H2O] (ipa =
isophthalate, phen = 1,10ꢀphenanthroline) extended
by
π
– stacking interaction from phen [18]. Hu and
π
our group have prepared two Co(II) metalꢀorganic
coordination polymers with leftꢀ and rightꢀhanded
helical chains such as [Co2(phen)2(1,4ꢀchdc)2(H2O)2
(chdc = cyclohexanedicarboxylate) and [Co(1,3ꢀ
BDC)(Dpdq)H2O] (H2O) (Dpdq = 2,3ꢀdiꢀ2ꢀ
]
·
pyridylquinoxaline) linked by hydrogen bonds [19,
20]. However, most of these helical coordination polyꢀ
mers are derived from the corresponding organic
dicarboxylates with the specific coordination angles.
The helical character of the title compound is due to
the twisty configuration of the dmbbbi and ultimately
the 1D chains are extended into doubleꢀstranded heliꢀ
100 200 300 400 500 600 700
Temperature ( C)
°
Fig. 4. The TG curve of compound 1.
RUSSIAN JOURNAL OF INORGANIC CHEMISTRY Vol. 56 No. 12 2011

1922
LIU et al.
optimal choice to study its cyclic voltammetry behavꢀ
ior, which is inexpensive and easy to prepare. Figure 5
shows the cyclic voltammograms at a bare CPE and
the 1ꢀCPE in 1 M H2SO4 solution at room temperaꢀ
ture. It can be seen from Fig. 5 that in the potential
range +100 to +800 mV, there is no redox peak at the
40
30
20
10
0
bare CPE. While
redox peak and the mean peak potential
pc)/2 is approximately 394 mV (100 mVs–1), which
1
ꢀCPE exhibits one quasiꢀreversible
E1/2 = (Epa
+
(a) bare CPE
E
could be attributed to the redox of Ni(II)/Ni(I) [25].
A new 3D supramolecular network derived from
leftꢀ and rightꢀhanded helical coordination polymers
has been obtained from a flexible double imidazole
derivative and 3,5ꢀdinitrobenzoate. The preparation
of the title compound demonstrates that the rational
design and select of organic ligands is the valid method
for the construction of metalꢀorganic coordination
polymer with helical structure. Moreover, the comꢀ
pound exhibits the remarkable thermal stability and
electrochemistry properties and may be a useful elecꢀ
trochemistry material.
–10
–20
–30
(b) 1ꢀCPE
100 200 300 400 500 600 700
(mV)
E
Fig. 5. Cyclic voltammograms of (a) the bare CPE, (b)
ꢀCPE in 1 M H SO solution in the potential range of
1
2
4
–1
100–750 mV. Scan rate: 100 mVs
.
cal chains by hydrogen bonds, which is structurally
different from that of the reported compounds.
ACKNOWLEDGMENTS
The main features in the IR spectrum of the title
compound concern the coordination water molecule,
the Nꢀligands, methylꢀ, the nitroꢀ and carboxyl
groups. The broad band at around 3400 cm–1 was
This work was supported by the NCETꢀ09ꢀ0853,
the National Natural Science Foundation of China
(no. 20871022) and the Foundation of Liaoning Provꢀ
ince (nos. 2009R03 and 2009A028).
assigned to the (O–H) vibration of coordinated water
ν
molecule [21]. The strong absorption peak at about
727 cm–1 and the weak absorptions at about 2943 and
ν
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