Zn coordination polymers based on designed of tetrazole-yl acylamide: Syntheses, structures and luminescence property

Full text of DOI:10.1016/j.molstruc.2017.09.054

Accepted Manuscript
Zn coordination polymers based on designed of tetrazole-yl acylamide: Syntheses,
structures and luminescence property
Xiao-Lan Tong, Chen Xiong, Jian-Qiao Lin, Jian-Hua Xin, Yin-Chong Ge, Fen Liu
PII:
S0022-2860(17)31241-3
10.1016/j.molstruc.2017.09.054
MOLSTR 24303
DOI:
Reference:
To appear in: Journal of Molecular Structure
Received Date: 19 July 2017
Revised Date: 13 September 2017
Accepted Date: 18 September 2017
Please cite this article as: X.-L. Tong, C. Xiong, J.-Q. Lin, J.-H. Xin, Y.-C. Ge, F. Liu, Zn coordination
polymers based on designed of tetrazole-yl acylamide: Syntheses, structures and luminescence
property, Journal of Molecular Structure (2017), doi: 10.1016/j.molstruc.2017.09.054.
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ACCEPTED MANUSCRIPT
Zn Coordination polymers based on designed of tetrazole-yl acylamide: syntheses,
structures and luminescence property
a,b,*
b
b
b
b
b
Xiao-Lan Tong , Chen Xiong , Jian-Qiao Lin , Jian-Hua Xin , Yin-Chong Ge , Fen Liu
a
Key Laboratory for radioactive Geology and Exploration Technology, Fundamental Science for National
Defense, East China University of Technology, NanChang, JX 330013, China;
b
School of Chemistry, Biology and Material Science, East China University of Technology, NanChang, JX
3
30013, China

ACCEPTED MANUSCRIPT
Zn Coordination polymers based on designed of tetrazole-yl acylamide: syntheses,
structures and luminescence property
a,b,*
b
b
b
b
b
Xiao-Lan Tong , Chen Xiong , Jian-Qiao Lin , Jian-Hua Xin , Yin-Chong Ge , Fen Liu
a
Key Laboratory for radioactive Geology and Exploration Technology, Fundamental Science for
National Defense, East China University of Technology, NanChang, JX 330013, China;
b
School of Chemistry, Biology and Material Science, East China University of Technology,
NanChang, JX 330013, China
1
1
1
Three Zn(II) coordination polymers, [Zn(L ) ] (1), [Zn(L )(5-ATZ)] (2) (HL =
2
n
n
2
2
N-(1H-tetrazol-5-yl)benzamide),
and
[Zn(L ) (H O)]
(3)
(L =
2
2
4
-methyl-N-(1H-tetrazol-5-yl)benzamide) have been synthesized under hydrothermal
conditions and characterized by single-crystal X-ray diffraction. Single-crystal X-ray
diffraction analyses showed that 1 and 2 both display two-dimensional architectures
4
with diverse topologies. Compound 1 was a 4 network based on Zn center, while
3
compound 2 presents a 6 topology. Compound 3 exhibits mononuclear structure,
which was connected to three-dimensional architecture by hydrogen bonds. In
addition, the fluorescence property and thermal stability of compound 1 have been
studied.
Keywords: Zn(II) coordination polymers
Thermal stability
Topology
Fluorescence property

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In recent years, the design and synthesis of coordination polymers are gaining
much more interest for their interesting structural topologies and wide potential
applications as functional materials [1]. However, it is a long-standing challenge to
design and synthesize new coordination polymers because of the central metals, the
nature of the organic ligands as well as some external factors, such as solvent,
temperature, pH value and anion, etc [2-8]. Therefore, in order to obtain novel
structures with desirable functions, the selecting and designing reasonable organic
ligands are particularly important [9]. Among diverse organic ligands, the polydentate
N donor ligands have been employed extensively as chelating or bridging linkers [10].
5
-substitued 1H-tetrazoles have been extensively used in the synthesis of polymeric
transition metal complexes due to their diversified coordination modes and structures
11]. However, examples of frameworks with the amide ligand of organic acid
containing tetrazolate group have seldom been involved up to now [12]. Meanwhile,
[
1
0
d
metal ions present variable coordination numbers and geometries, and their
compounds generally exhibit luminescent properties [13]. In this article, we use the
1
2
amide ligand of benzoic acid containing tetrazolate group HL and HL successfully
1
presenting their three novel Zn Coordination polymers, [Zn(L ) ] (1),
2
n
1
2
[
Zn(L )(5-ATZ)] (2) and [Zn(L ) (H O)] (3), and their structures were determined by
n 2 2
single-crystal X-ray diffraction studies, also the fluorescence property and thermal
stability of 1 have been studied.
1
. Materials and method
All chemicals in the reactions were obtained from commercial sources without
further purification excepting the ligands. The ligands N-(1H-tetrazol-5-yl)benzamide)
1
2
(
HL ) and 4-methyl-N-(1H-tetrazol-5-yl)benzamide) (HL ) were synthesized
according to the literature method [14,15], see part of syntheses.
Elemental analyses (C, H, and N) were performed on a Perkin-Elmer 240C analyzer,
and IR spectra were measured on a Tensor 27 OPUS (Bruker) FT-IR spectrometer
with KBr pellets. Emission spectra were taken on an F-4500 spectrofluorometer.
Thermal stability (TG-DTA) studies were carried out on a Dupont thermal analyzer
from room temperature to 800 °C at a rate of 10 °C·min-1. The X-ray powder

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diffraction (XRPD) was recorded on a Rigaku D/Max-2500 diffractometer at 40 kV,
1
00 mA for a Cu-target tube and a graphite monochromator. Simulation of the XRPD
spectra was carried out by the single-crystal data and diffraction-crystal module of the
Mercury (Hg) program available free of charge via the Internet at http://www.iucr.org.
2
. X-ray crystallography
Compounds 1-3 were collected on a computer-controlled carried out on a
Scx-Mini diffractometer equipped with a graphite crystal monochromator situated in
the incident beam. The determinations of unit cell parameters and data collections
were performed with Mo-K
α radiation (λ = 0.71073 Å) at 293(2) K and unit cell
dimensions were obtained with least-squares refinements. The program SAINT [16a]
was used for integration of the diffraction profiles. All the structures were solved by
direct methods using the SHELXS program of the SHELXTL package and refined by
full-matrix least-squares methods with SHELXL [16b]. Metal atoms in the
compounds were located from the E-maps and other non-hydrogen atoms were
located in successive difference Fourier syntheses and refined with anisotropic
2
thermal parameters on F . The hydrogen atoms of the ligand were generated
geometrically. The detailed crystallographic data and selected bond dimensions for
1
-3 are listed in Table 1 and 2. CCDC numbers: 899262, 899264, 899265.
Table 1
Crystallographic data and structure refinement details for compounds 1-3.
1
2
3
Empirical formula
Formula weight
Crystal system
Space group
T/K
C H ZnN O
C H ZnN O
C H ZnN O
3
1
6
12
10
2
9
7
10
18 18
10
441.73
336.62
487.82
orthorhombic
Pbca
monoclinic
monoclinic
Cc
P2 /c
1
293(2)
8.4416(17)
9.5149(19)
20.268(4)
90
293(2)
10.270(2)
10.406(2)
13.206(3)
90
293(2)
9.809(2)
11.830(2)
17.643(3)
90
a/Å
b/Å
c/Å
α
β
/()
/deg
90
97.08(3)
90
95.12(3)
90
γ/deg
90

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3
V/Å
1628.0(6)
1400.2(5)
4
2.39.1(6)
4
Z
4
−3
D /g cm
1.802
1.597
1.589
c
−1
µ
/mm
1.551
1.770
1.250
F(000)
896
676
1000
Reflnsmessured
Obsd reflns
15743
11799
10335
1859
2467
2331
a
b
R /wR [I>2σ(I)]
0.0388/0.0920
0.0500/0.0969
2
0.0597/0.0892
0.0840/0.0952
2 1/2
0.0682/0.1334
0.1037/0.1479
1
2
R , wR (all data)
1
2
a
b
2 2
R = Σ(||F | – |F ||)/Σ|F |. wR = [Σ(|F | – |F | ) /Σ(F )]
o
c
o
o
c
o
Table 2
Selected bond distances (Å) and angles (deg) for 1-3
1
Zn(1)-N(2)
Zn(1)-O(1B)
Zn(1)-N(5C)
2.122(2)
2.0991(17)
2.265(2)
Zn(1)-O(1)
2.0991(17)
2.122(2)
2.265(2)
Zn(1)-N(2B)
Zn(1)-N(5D)
O(1)-Zn(1)-O(1B)
O(1B)-Zn(1)-N(2)
O(1B)-Zn(1)-N(2B)
O(1)-Zn(1)-N(5C)
N(2)-Zn(1)-N(5C)
O(1)-Zn(1)-N(5D)
N(2)-Zn(1)-N(5D)
N(5C)-Zn(1)-N(5D)
2
180.0
O(1)-Zn(1)-N(2)
85.58(7)
94.42(7)
180.00(11)
87.53(7)
100.22(7)
92.47(7)
79.78(7)
94.42(7)
85.58(7)
92.47(7)
79.78(7)
87.53(7)
100.22(7)
180.00(8)
O(1)-Zn(1)-N(2B)
N(2)-Zn(1)-N(2B)
O(1B)-Zn(1)-N(5C)
N(2B)-Zn(1)-N(5C)
O(1B)-Zn(1)-N(5D)
N(2B)-Zn(1)-N(5D)
Zn(1)-N(9A)
1.970(4)
1.991(3)
2.212(3)
Zn(1)-N(6)
1.977(4)
2.199(4)
Zn(1)-N(1)
Zn(1)-N(2B)
Zn(1)-O(1)
N(9A)-Zn(1)-N(6)
N(6)-Zn(1)-N(1)
N(6)-Zn(1)-N(2B)
N(9A)-Zn(1)-O(1)
N(1)-Zn(1)-O(1)
3
120.09(15)
119.56(15)
91.74(14)
86.77(14)
81.25(13)
N(9A)-Zn(1)-N(1)
N(9A)-Zn(1)-N(2B)
N(1)-Zn(1)-N(2B)
N(6)-Zn(1)-O(1)
118.77(14)
91.34(15)
99.48(13)
89.42(14)
178.09(14)
N(2B)-Zn(1)-O(1)

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Zn(1)-O(1W)
Zn(1)-N(5)
Zn(1)-O(1)
1.990(5)
Zn(1)-N(5A)
Zn(1)-O(1A)
2.010(3)
2.096(3)
2.010(3)
2.096(3)
O(1W)-Zn(1)-N(5A)
N(5A)-Zn(1)-N(5)
N(5A)-Zn(1)-O(1A)
O(1W)-Zn(1)-O(1)
N(5)-Zn(1)-O(1)
119.14(10)
121.72(19)
83.70(11)
88.21(8)
O(1W)-Zn(1)-N(5)
O(1W)-Zn(1)-O(1A)
N(5)-Zn(1)-O(1A)
N(5A)-Zn(1)-O(1)
O(1A)-Zn(1)-O(1)
119.14(10)
88.21(8)
98.07(11)
98.07(11)
176.41(16)
83.70(11)
Symmetry codes: For 1: A: x+1/2,-y+1/2,-z+1; B: -x,-y+1,-z+1; C: x-1/2,-y+1/2,-z+1; D:
x+1/2,y+1/2,z.; For 2: A: -x+1,y+1/2,-z+1/2; B: -x+1,-y+2,-z+1; C: -x+1,y-1/2,-z+1/2; For 3:
A:-x,y,-z+1/2.
-
3
. Syntheses of part
1
3
.1 N-(1H-tetrazol-5-yl)benzamide) (HL )
Anhydrous tetrahydrofuran (60 mL) containing 5-aminotetrazolate (0.1 mol) was
in an ice bath for 30 min, benzoyl chloride (0.1 mol) was slowly added to the above
solution, then the obtained solution was stirred overnight. The white solid was
collected, washed with water, and dried to give 13.65g of the ligand, see Chart 1. The
yield was ~70%。m.p. 270 °C. Anal. Calcd for C H N O: C, 50.79; H, 3.73; N, 37.02.
8
7
5
1
Found: C, 50.36; H, 3.81; N, 36.84. H NMR(DMSO-d )： 7.54~7.60 (m，2H，ArH)，
6
-1
8
.07~8.12 (m，2H，PyH)，12.44 (s，1H，N H)。IR (KBr pellet，cm )：3212m, 3069m,
4
1
669s, 1593s, 1547m, 1448w, 1228m, 1036s, 937w, 900s, 803m, 702s, 660m。
2
3
.2 4-methyl-N-(1H-tetrazol-5-yl)benzamide) (HL )
2
1
The preparation of HL was synthesized in a similar procedure as HL , by using
-methyl benzoyl chloride in place of benzoyl chloride, and the yield was 60%. m.p.
55 °C. Anal. Calcd for C H N O: C, 53.20; H, 4.46; N, 34.47. Found: C, 52.93; H,
4
1
4
7
9
9
5
1
.61; N, 34.22. H NMR(DMSO-d )：2.35 (m，3H，CH ，7.24 (m，2H，ArH)，
6
3)
.83(m，2H，ArH)，δ 8.0(s，H，Amide NH)，15.8(s，1H，N H)。IR (KBr pellet,
4
−1
cm ): 3413(s), 1639(s), 1617(s), 1400(m), 1274(w), 1059(w), 995(w), 619(m).

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O
N
H
N
N
N
Furan
Ice bath
N
N
H N
2
Cl
HN
N
HN
O
HL1
O
N
H
N
N
Furan
Ice bath
N
N
H N
2
N
Cl
HN
N
HN
O
HL2
1
2
Chart 1 Synthesis of HL and HL
1
3
.3 [Zn(L ) ] (1)
2
n
1
A mixture of ZnCl (81.6 mg, 0.6 mmol), HL (56.7 mg, 0.3 mmol ) and water
2
(12 mL) was sealed in a 25 mL Teflon-lined stainless steel vessel and heated at 140 °C
–
1
for 48 h, then cooled to room temperature at a rate of 10 °C·h . Colorless
prism-shaped crystals of 1 were isolated and washed with water and ethanol and dried
1
in air (ca. 36% yield based on HL ). Anal. Calcd for C H ZnN O : C, 43.50; H,
1
6
12
10
2
−
1
2
3
8
.74; N, 31.71. Found: C, 43.06; H, 2.91; N, 31.42. IR (KBr pellet, cm ): 3407(w),
237(w), 1650(s), 1566(m), 1584(s), 1445(m), 1248(w), 1021(m), 929(w), 896(s),
08(m), 731(s), 657(m).
1
3
.4 [Zn(L )(5-ATZ)] (2)
n
2
A mixture of ZnCl (68.0 mg, 0.5 mmol), HL (56.7 mg, 0.3 mmol ), NH VO
2
4
3
(70.2 mg, 0.6 mmol ) and water (12 mL) was sealed in a 25 mL Teflon-lined stainless
steel vessel and heated at 160 °C for 72 h, then cooled to room temperature at a rate of
–
1
5
°C·h . Colorless bulk crystals of 2 were isolated and washed with water and
−
1
ethanol and dried in air. IR (KBr pellet, cm ): 3430(w), 3239(w), 3026(w),1650(m),
1
566(m), 1445(w), 1209(s), 1157(s), 914(m), 698(m), 657(w).
2
3
.5 [Zn(L ) (H O)] (3)
2
2
2
A mixture of ZnCl (1.0 mmol), HL (0.5 mmol ), NaN (1.0 mmol ) and water
2
3
(12 mL) was sealed in a 25 mL Teflon-lined stainless steel vessel and heated at 160 °C
–1
for 72 h, then cooled to room temperature at a rate of 5 °C·h . Colorless
prism-shaped crystals of 1 were isolated and washed with water and ethanol and dried
−1
in air. IR (KBr pellet, cm ): 3423(w), 3227(w), 1630(s), 1475(m), 1410(w), 1025(m),
9
20(m), 750(s), 685(m).
Caution! Although we have met no problems in handling tetrazoles and their
compounds during this work, it should be treated with great caution owing to their
potential explosive nature.

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4
. Molecular structure
1
4
.1 [Zn(L ) ] (1)
2
n
Single-crystal X-ray diffraction analysis shows that compound 1 crystallizes in
Pcba space group, and the asymmetric unit contains half crystallographically
II
1
II
independent Zn center and one L ligand. Each Zn center shows a coordination
number of six, surrounded by four N atoms and two O atoms from four independent
1
II
1
L . The Zn center is chelated by two L through their O atoms and N atoms of
tetrazolate rings, forming the equatorial plane that contains two six-membered rings,
1
the N atoms of tetrazolate rings from other two L occupying the axial positions (Fig.
1
a). The Zn–N distances are 2.122(2) and 2.265(2) Å and Zn–O bonds are 2.0991(17)
II
Å, respectively, and coordination angles around Zn center vary from 79.78(7) to
II
1
80.00(7)°, which indicate the octahedral geometries around Zn center are slightly
distorted. All the Zn–N and Zn–O are within the ranges expected for such
17
II
complexes. The deprotonated L acts as tridentate bridging ligand linking two Zn
1
centers with distance of 6.360 Å, the tetrazolate rings of L in 1 adopt ꢀ bridging
1
,4
1
II
coordination mode and the whole L link Zn center into 2D structure in the ab plane.
4
The connectivity of the network of 1 can be simplified to a (4 ) topology with the
metal centers are simplied as 4-connecting nodes (Fig. 1b).
(
Insert Figure 1)
(a)

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(b)
II
4
Fig. 1. (a) The local coordination geometry around the Zn centers in 1; (b) The 2D (4 )
framework structure.
1
4
.2 [Zn(L )(5-ATZ)] (2)
n
When the ammonium metavanadate was added and the reaction temperature was
up to 160°C, a different structure of 2 was obtained. Single-crystal X-ray diffraction
II
1
analysis reveals that the asymmetric unit of 2 contains one Zn center, one L and one
II
5
-ATZ. The Zn center is five-coordinated by four nitrogen atoms and one oxygen
1
atom from two 5-ATZ ligands and two L ligands (Fig. 2a). The Zn–N bond lengths
vary from 1.970(4) to 2.199(4) Å and the Zn–O bond is 2.212(3) Å, the coordination
II
angles around Zn center vary from 86.77(14) to 178.09(14)°. The 5-ATZ adopts a
1
ꢀ1,4
bridging coordination fashion, while L takes tridentate coordination mode
II
linking two Zn centers with the distance of 4.068 Å, in which the tetrazole ring adopt
1
II
ꢀ1,2
bridging coordination mode. In this way, the 5-ATZ and L link the Zn centers to
II
form a 2D layer (Fig. 2b). Topologically, if the Zn ions are considered as
3
3
-connected node, the 2D layer can be simplified as a 3-connected net with the (6 )
topology (Fig. 2c).

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II
Fig. 2. (a) The local coordination geometry around the Zn centers in 2; (b) The 2D layer in the
3
bc plane; (c) The 2D (6 ) framework structure.
2
4
.3 [Zn(L ) (H O)] (3)
2
2
II
The structure of 3 contains one independent crystallographically Zn center, two
2
II
L ligands in general position and one coordination water molecular. Each Zn center
2
in the mononuclear motif is chelated by two L ligand through their oxygen atoms and
nitrogen atoms of tetrazolate rings as well as one oxygen atom of the coordinated
water molecular to complete a distorted trigonal biyramidal geometry (Fig. 3a). The
Zn1–O distances are 1.990(5) and 2.096(3) Å and Zn1–N bonds are 2.010(3) Å,
II
respectively, and the coordination angles around Zn center vary from 83.70(11) to
II
1
76.41(16)°. All the bond lengthes and bond angles around the Zn atom are in the
normal ranges for such complexes[17]. The 3D structure of 3 are linked by C-H···N,
C-H···O and O-H···N hydrogen bonds between the adjacent molecules (Table S1 and
Fig. 3b).

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II
Fig. 3. (a) The diagram of the coordination mode of Zn centers in 3; (b) The 3D supramolecular
structure of 3 connected by hydrogen bonds.
5
. Summary of the Structures
1
Compound 1 was obtained through lignad HL and ZnCl at the temperature of
2
1
40 °C, while compound 2 was obtained when ammonium metavanadate was added
and the reaction temperature was up to 160°C, and its structure is different from
compound 1, also the 5-ATZ existing in compound 2, which may be from the
1
2
decomposition of the L under higher temperature. When the HL and NaN was used,
3
2
compound 3 has been synthesized as mononuclear, where HL have one more methyl
1
1
2
than HL in its structure. H L and H L can act as either bidentate or tridentate
2
2
ligands when coordinating to Zn metal ions under different conditions, and three
coordination modes for tetrazolate rings have been observed in these three compounds
(Chart 2). The ligands are all deprotonated to form monovalent anionic derivatives.

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(a)
(b)
(c)
1
1
Chart 2 (a) the coordination modes of HL in complex 1; (b) the coordination modes of HL in
2
complex 2; (c) the coordination modes of HL in complex 3.
Because of the poor productivity of compound 2 and 3, their photoluminescent
property and thermal analyses have not been studied.
6
. Photoluminescent property
It is well known that luminescence compounds have attracted much attention
recently because of their potential applications in photochemistry, chemical sensors
and structure electroluminescence (EL) display[18], especially for the luminescent
10
properties of tetrazolate compounds with d metal ions[19]. Here we have been
exploring the luminescence property of compound 1 in the solid state at room
1
temperature (Fig.4). The free HL ligand displays a very weak emission centered at ca.
3
70 nm in the solid state at ambient temperature. For compound 1, its radiation
emission maxima at ca. 375 nm, which shifts to longer wavelength only several
*
nanometers, can likely be attributed to the π-π or π-n electronic transitions within
10
ligand-centered aromatic systems, by comparison with other luminescent d metal
coordination polymers[20].

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Fig. 4. Solid-state fluorescence spectra of compound 1 at room temperature.
7
. Thermal analyses
In order to determine the thermal stability of compound 1, thermogravimetric
analysis (TGA) for 1 was performed by heating the corresponding compound from 20
-1
to 800 °C in air at a rate of 10 °C·min . The TGA result of 1 indicates that compound
1
decomposed upon to 340 °C, with further heating, a rapid weight loss occurs, which
is due to the departure of organic ligand(Fig. S1). The thermal analysis indicates that
complex 1 has high thermal stability.
8
. XRPD Results
To confirm whether the analyzed crystal structures are truly representative of the
bulk materials, XRPD experiments were carried out for compound 1. The XRPD
experimental and computer-simulated patterns of the corresponding compound is
shown in Fig. S2. It is in good agreement with each other, which prove the phase
purity of the as-synthesized product and the properties of compound 1 were
believable.
9
. Conclusion
In summary, three compounds have been obtained by a hydrothermal method
1
2
II
using the tetrazole ligands HL and HL , as well as the corresponding Zn salts. The

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difference in the frameworks of the target compounds are due to the influences of the
nature of the reaction conditions and the different structures of the ligands. Also the
fluorescence property and thermal stability of compound 1 have been studied. It is
anticipated that more metal compounds containing our obtained ligands here with
charming structures as well as physical properties will be synthesized in future.
Acknowledgments
This work was financially supported by the Natural Science Foundation of China
(21461001), the Project of Jiangxi Provincial Department of Education (Grant No.
GJJ13448), the open fund of Fundamental Science on Radioactive Geology and
Exploration Technology Laboratory (REGT1212), the open fund of State Key
Laboratory for Nuclear Resources and Environment (NRE1510).

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Zn Coordination polymers based on designed of tetrazole-yl acylamide: syntheses,
structures and luminescence property
a,b,*
b
b
b
b
b
Xiao-Lan Tong , Chen Xiong , Jian-Qiao Lin , Jian-Hua Xin , Yin-Chong Ge , Fen Liu
a
Key Laboratory for radioactive Geology and Exploration Technology, Fundamental Science for National
Defense, East China University of Technology, NanChang, JX 330013, China;
b
School of Chemistry, Biology and Material Science, East China University of Technology, NanChang, JX
3
30013, China
4
3
ꢀ
ꢀ
ꢀ
Compound 1 and 2 are both 2D structures with 4 and 6 networks, respectively.
Compound 1 exhibits high thermal stability and intense fluorescence behavior.
The structural differences are owing to different reaction conditions and ligands.