Polyhedron 144 (2018) 1–5

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

Syntheses, crystal structures, luminescence and thermal properties of

three lanthanide complexes with 2-bromine-5-methoxybenzoate and
2,2:60 ,200 -terpyridine
Zhao Qing-Qing a,b, Ren Ning c,⇑, Zhang Jian-Jun a,b,⇑
a
Testing and Analysis Center, Hebei Normal University, Shijiazhuang 050024, PR China
b
College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024, PR China
c
College of Chemical Engineering & Material, Handan University, Handan 056005, Hebei Province, PR China

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

Article history: Three new mononuclear lanthanide complexes [Ln(2-Br-5-MOBA)3(terpy)(H2O)] (Ln = Gd (1), Tb (2), Er
Received 5 December 2017 (3); 2-Br-5-MOBA = 2-bromine-5-methoxybenzoate; terpy = 2,2:60 ,200 -terpyridine) have been success-
Accepted 29 December 2017 fully synthesized and characterized by single-crystal X-ray diffraction. The complexes 1–3 were isostruc-
Available online 8 January 2018
tural and eight-coordinated, which is different from the binuclear structure of the previously reported
complexes. The molecular structure of complexes 1–3 is very interesting: two adjacent mononuclear
Keywords: units are connected through hydrogen bonding giving rise to a pseudo binuclear structure. These pseudo
Lanthanide complexes
binuclear units are further linked via O–H  Br hydrogen bonds and slightly offset p–p stacking interac-
Crystal structure
Thermal analysis
tions to from 1D and 2D supramolecular structures. The thermal decomposition mechanism of complexes
Luminescence 1–3 was studied by TG analysis and further authenticated by TG/DSC-FTIR techniques. The solid-state
2,2:60 ,200 -Terpyridine luminescent property of complex 2 was investigated at room temperature. The result indicates that Tb
(III) complex appear to be promising candidate for the application as green luminescent material.
Ó 2018 Elsevier Ltd. All rights reserved.

1. Introduction
In recent years, the search of lanthanide complexes has
attracted great interest for their potential applications in light-
emitting diodes [1], luminescent probes [2,3], magnetic materials
[4,5], catalysts [6,7], thermodynamics [8,9] and antibacterial [10].
Due to the high coordination number and flexible coordination
geometry, more and more lanthanide complexes with novel struc-
ture have been synthesized [11]. Aromatic carboxylic acid ligands
exhibit high affinity for lanthanide cations because of the presence
of the hard donor oxygen atoms [12], making them become a bet-
ter choice for the construction of lanthanide complexes. And the
carboxylic acid ligands have many coordination modes, which
makes the lanthanide complex containing aromatic-carboxylic
acids produce a considerable number of structures [12,13].
Due to the intense emission of lanthanide ions over narrow
wavelength ranges, fluorescence has been extensively discussed
in all applications of lanthanide complexes [11]. In particular, those
containing Eu (III) and Tb (III) have long-lived emission and have
⇑ Corresponding authors at: Testing and Analysis Center, Hebei Normal Univer-
sity, Shijiazhuang 050024, PR China (J.-J. Zhang). Fax: +86 31180786457.
E-mail addresses: ningren9@163.com (N. Ren), jjzhang6@126.com (J.-J. Zhang).
been candidates for red and green materials. However, the parity
inhibition of f–f transitions leads to the low absorption coefficients
of Ln (III). Therefore, a suitable chromophore (antenna) is helpful to
trigger their emission through efficiently energy transfer from the
ligand to the rare earth ions [14–17]. Recently, many researchers
have introduced auxiliary organic ligands in the preparation of
complexes, since N-containing heterocyclic auxiliary ligands usu-
ally make lanthanide complexes exhibit higher thermal stability
and stronger luminescence [18].
Herein, we report the synthesis of three coordination complexes
[(Ln(2-Br-5-MOBA)3(terpy)(H2O)] (Ln = Gd (1), Tb (2), Er (3);
2-Br-5-MOBA = 2-bromine-5-methoxybenzoate; terpy = 2,2:60 ,
00
2 -terpyridine), which are characterized by elemental analysis, IR
spectra, single crystal X-ray diffraction, and thermal stability.
Furthermore, the solid-state luminescent property of complex 2
is also studied.
2. Experimental
2.1. Materials and general methods
LnCl36H2O was prepared via the reaction of Ln2O3 (Ln = Gd, Tb,
Er, Beijing Lanthanide Innovation Technology Co., Ltd, solid, 99.9%)

https://doi.org/10.1016/j.poly.2017.12.036
0277-5387/Ó 2018 Elsevier Ltd. All rights reserved.
2 Q.-Q. Zhao et al. / Polyhedron 144 (2018) 1–5
and hydrochloric acid in aqueous solution, then the liquid was
evaporated by water bath heating at a constant temperature of
353.15 K. Other analytically pure chemicals were purchased and
used without further purification.
2.2. Experimental equipment and conditions
Elemental analysis of the complexes was carried out using the
Vario-EL II element analyzer and the Ln content was assayed by
EDTA chelatometric titration method. The IR spectra were recorded
in the range of 4000–400 cm1 on a Bruker TENSOR 27 spectrom-
eter using the KBr medium pellets at room temperature. The single
crystal X-ray diffraction data of complexes 1–3 were obtained on a
Smart-1000 diffractometer with graphite-monochromated Mo Ka
radiation (k = 0.71073 Å) at 298(2) K. The structure was resolved
by direct methods using the SHELXS-97 program and refined with
full-matrix least-squares on F2 using the SHELXL-97 program.
The thermogravimetric (TG), differential thermogravimetric
(DTG) and Fourier transform infrared (FTIR) analysis of the com-
plexes 1–3 were conducted at a heating rate of 10 K min1 (simu-
lated air atmosphere) on a TG/DSC-FTIR system, which was a
NETZSCH STA 449 F3 instrument with a Bruker TENSOR27 Fourier
transform infrared spectrometer. The NETZSCH STA 449 F3 instru-
ment was linked to the heated gas cell of the FTIR instrument by
means of a heated transfer line kept at 473.15 K.
In addition, the fluorescent spectra of complex 2 was measured
on an F-4600 Hitachi spectrophotometer at room temperature and
the solid fluorescence quantum yield of the complex 2 was mea-
sured using C9920-02G Hamamatsu test system, which was con-
stituted by integrating sphere of 10-inch diameter and connected
to a CCD detector.
2.3. Preparation of complexes
A mixture of 2-Br-5-MOHBA (0.6 mmol) and terpy (0.2 mmol)
was dissolved in 6 mL 95% ethanol solution and adjust the pH of
the mixture solution to 6–7 with 1 mol L1 NaOH solution. Then
add dropwise the mixture to the aqueous solution of LnCl36H2O
(0.2 mmol) under stirring and continually stir about 7 h. The pow-
ders of title complexes were obtained after depositing overnight,
filtering and drying. The single crystals were collected from the
mother liquor after two weeks at room temperature. Elemental
analyses for C39H31Br3N3O10Gd (%), Calcd: C, 42.64; H, 2.84; N,
3.82; Gd, 14.31. Found: C, 42.55; H, 2.81; N, 3.79; Gd, 14.23 (yield:
58.86%). For C39H31Br3N3O10Tb (%), Calcd: C, 42.57; H, 2.84; N,
3.82; Tb, 14.44. Found: C, 42.46; H, 2.82; N, 3.78; Tb, 14.37 (yield:
56.44%). For C39H31Br3N3O10Er (%), Calcd: C, 42.25; H, 2.82; N, 3.79;
Er, 15.09. Found: C, 42.20; H, 2.82; N, 3.73; Er, 15.01 (yield:
59.83%).
3. Results and discussion
3.1. Infrared spectroscopy
As we all know, the IR spectra can provide valuable information
regarding the functional group attached to the center metal ions.
The result of infrared spectra for title complexes and ligands indi-
cates that complexes 1–3 are isostructural, which is verified by sin-
gle crystal X-ray diffraction analysis. The main characteristic
absorption bands of the ligands and their complexes 1–3 are pre-
sented in Table 1. The IR spectrum of the free organic carboxylic
ligand 2-Br-5-MOHBA has a strong absorption at 1703 cm1, which
was assigned to the stretch vibration of the carboxylate group
(mC@O). The band disappear in the IR spectrum of all complexes
and appear two new absorbing bands at 1621–1623 cm1 and
1419–1420 cm1, belonging to the asymmetric (masðCOO Þ ) and sym-
metric (msðCOO Þ ) stretching vibrations, respectively. At the same
time, the bands at 417–421 cm1 in the complexes correspond to
the vibrations of LnAO. These changes show that oxygen atom of
the carboxylate groups coordinate to the Ln (III) ion [19]. What’s
more, the peaks of mC@N for terpy are observed at 1559 cm1 take
place red shift to 1522–1523 cm1, which suggests that three
nitrogen atoms of terpy participate in the coordination to the Ln
(III) ions [20].
3.2. Description of crystal structures
The single-crystal X-ray structures of three complexes were
determined. The most important crystallographic data and data
collection parameters are shown in Table S1, indicating the three
complexes are isostructural and crystallize in the triclinic with
space group P1.  Therefore, as a representative example, the crystal
structure of the complex 1 will be discussed in detail.
The asymmetric unit of 1 consists of one Gd (III) ion, three 2-Br-
5-MOBA ligands, one terpy ligand and one coordination water
molecule. As shown in Fig. 1a, Gd1 ion is eight-coordinated by four
carboxylate oxygenatoms (O1, O4, O7, and O8) from three 2-Br-5-
MOBA ligands, one oxygen atoms (O10) from the coordination
water molecule, and three nitrogen atoms from the terpy ligand.
Three 2-Br-5-MOBA ligands have two different coordination
modes: chelating monodentate and chelating bidentate. The coor-
dination environment around the Gd (III) ion can be described as a
slightly distorted square antiprismatic molecular geometry struc-
ture (Fig. 1b). The GdAO bond distances range from 2.269(5) to
2.586(5) Å for 2 and the average GdAN bond distance is 2.546 Å
(Table 2), which are comparable to those reported complexes.
The average lengths of GdAO and GdAN are 2.388 Å and 2.513 Å
in {[Gd2(HL)3(H2O)3]3H2O}n, respectively [11]. It can be seen that
the bond lengths of the LnAO and LnAN slightly decrease as the
increase of atomic numbers, which is consistent with lanthanide
contraction rule. In addition, the average bond length for LnAN is
longer than that of LnAO. The result is consistent with the first loss
of 2,20 -bipy molecule in the first thermal decomposition process.
Two adjacent units of complex 1 are connected through hydro-
gen bonding interactions involving oxygen atoms (O10) from coor-
dinated water molecules and oxygen atoms (O2 and O5) from
carboxylate groups (d (O10  O2) = 2.874 Å; d (O10  O5) = 2.774
Å) giving rise to a pseudo binuclear structure, as shown in
Fig. 2a. The O–H  Br hydrogen bonds further link these pseudo
binuclear units into a 1D supramolecular chain structure along
the  direction (d (O5  Br) = 3.120) (Fig. 2b). At the same time,
the slightly offset p–p stacking interactions between terpy ligands
on neighboring units induce the 1D chains into a 2D supramolecu-
lar framework viewed along the xy plane (Fig. 2c). These non-
covalent interactions are between the centroid of the terpy ring
on one unit and the edge of the terpy ring on the neighboring unit
with the relevant distances and angles: Cg  Cg  3.3344(88) Å;
Cg\  Cg\  3.5899(2) Å; b = 68.227(399)°.
At 2015, Zong et al. have reported the structure of [Er2(2-Br-5-
MOBA)6(phen)2] (2-Br-5-MOBA = 2-bromine-5-methoxybenzoate,
phen = 1,10-phenanthroline) [21]. It is binuclear with a coordina-
tion number of nine and crystallizes in the triclinic space group
 The carboxylic acid ligands adopt three different coordination
P1.
modes: bridging, bidentate chelating, and tridentate chelating
bridging. The difference of auxiliary ligands may affect the coordi-
nation mode of the carboxylic acid ligands so that generate differ-
ent molecular structure. The average bond length of the Er–N is
2.533(19) Å for [Er2 (2-Br-5-MOBA)6(phen)2], while the length is
2.497 Å for complex 3. The shorter bond length indicates that the
terpy ligand has a stronger affinity to the Ln3+ ions than the phen
 Q.-Q. Zhao et al. / Polyhedron 144 (2018) 1–5 3

Table 1
The main IR absorption bands of the ligands and title complexes.

ligands/complexes mC@N dCAH mC@O masðCOO Þ msðCOO Þ mLnAO

Terpy 1559 762 661 – – – –
2-Br-5-MOHBA – – – 1703 – – –
1 1522 779 653 – 1621 1419 417
2 1522 779 651 – 1622 1420 420
3 1523 779 652 – 1622 1419 419

3.3. Thermal analysis

The thermal stability of complexes 1–3 was examined by ther-

Fig. 1. (a) Crystal structure of complex 1, all H atoms omitted for clarity. (b)
Coordination geometry of Gd3+ ion.
mogravimetric analysis (TGA) in the temperature range of 300–
1050 K in a simulated air atmosphere at a heating rate of 10 K
min1. The profiles of the TGA, DTG and DSC of the complex 2
are shown in Fig. 3 and the date of thermal analysis for the title
complexes are listed in Table S2. Complexes 1–3 are isomorphous
and exhibit similar TGA curves, thus only the thermal decomposi-
tion process of 2 will be discussed in detail. At least five main
degradation steps can be observed in the TGA curve of 2 (Fig. 3).
The first stage of weight loss about 1.65% from 355.15 to 404.15
K could be attributed to the loss of one coordinated water mole-
cules (Calcd: 1.64%), and there is a small endothermic peak in
DSC curve (Tp = 388.85 K; DH = 62.4 kJ mol1). The second stage
of weight loss 37.12% between 404.15 and 689.15 K corresponds
to the release of one terpy ligand and part 2-Br-5-MOBA ligand
(Calcd: 21.20%), which is an exothermic process observed from
the DSC curve (Tp = 600.65 K; DH = 101.9 kJ mol1). Then the
weight losses of 2 are divided into three steps at 689.15–
1019.15 K, corresponding to the loss of 2-Br-5-MOBA. There are
three exothermic peaks on the DSC curve (Tp = 775.15 K, DH =
260.1 kJ mol1; Tp = 885.75 K, DH = 2057 kJ mol1; Tp =
922.25 K, DH = 259.7 kJ mol1). The remaining weight of 17.39%
corresponds to the metallic oxide Tb4O7, which is agreement well
with the calculated value of 16.99%. It can be seen from the data
that the thermal stability of the three complexes is not very good,
which may be the result of existing coordination water molecule.

3.4. Evolved gas analysis during thermal decomposition

ligand. At 2016, Wang et al. reported the complex [Tb(2,4-
DClBA)3(terpy)(H2O)]H2O[22]. The complex has the same crystal
system and mononuclear structure with complex 2, but the coordi-
nation number is nine. The mononuclear units are stitched
together via O–H  O, C–HO hydrogen bonding and Cl-p interac-
tions to form supramolecular 1D chain, 2D sheet and 3D network
structures, which is different from the pseudo binuclear structure
of 2. The binuclear structures of [Ln(2,3-DClBA)3(terpy)(H2O)]2
(2,3-DClBA = 2,3-dichlorobenzoate) were synthesized by Wu
et al. in 2015 [23] are completely different from the mononuclear
structures in this paper. Thus, the acid ligands also play an impor-
tant role in the formation of different molecular structures.
Fig. 4 displays the TG-FTIR spectra of the evolved gas products
of thermal decomposition processes for complex 2, which are
recorded under simulated air atmosphere with a heating rate of
10 K/min by TG/DSC-FTIR system. Complexes 1–3 have similar
thermal decomposition process, thus only the complex 2 will be
discussed in detail. And the IR spectra of the evolved gases for 2
at different temperature are shown in Fig. S3.
The spectrum at T = 391.71 K shown in Fig. 5 corresponds to the
IR spectrum of the evolved gas in the first thermal decomposition
process. The absorption band at 1508 cm1 is attributed to the
bending mode in gaseous H2O and the bands at 3735 and

Table 2
The selected bond lengths (Å) for complexes 1–3.

Complex 1 Complex 2 Complex 3

Bond length (Å) Bond length (Å) Bond length (Å)
Gd(1)–O(4) 2.269(5) Tb(1)–O(1) 2.250(5) Er(1)–O(1) 2.214(5)
Gd(1)–O(1) 2.381(6) Tb(1)–O(7) 2.350(6) Er(1)–O(7) 2.300(5)
Gd(1)–O(10) 2.406(5) Tb(1)–O(10) 2.392(5) Er(1)–O(10) 2.345(5)
Gd(1)–O(7) 2.421(5) Tb(1)–O(5) 2.409(5) Er(1)–O(5) 2.375(5)
Gd(1)–N(1) 2.532(6) Tb(1)–N(1) 2.506(7) Er(1)–N(1) 2.482(6)
Gd(1)–N(3) 2.532(7) Tb(1)–N(3) 2.523(7) Er(1)–N(3) 2.490(7)
Gd(1)–N(2) 2.573(6) Tb(1)–N(2) 2.537(6) Er(1)–N(2) 2.504(6)
Gd(1)–O(8) 2.586(5) Tb(1)–O(4) 2.564(5) Er(1)–O(4) 2.525(5)
4 Q.-Q. Zhao et al. / Polyhedron 144 (2018) 1–5

Fig. 3. TG-DTG/DSC curves of the complex 2.

Fig. 4. Stacked plot of the FTIR spectra of evolved gases for complex 2.

Fig. 2. (a) The pseudo binuclear structure of complex 1. (b) 1D chain structure along
x-axis. (c) 2D sheet in about the xy plane via slightly offset p–p stacking
interactions.

3649 cm1 are attributed to the asymmetric and symmetric

stretches of H2O. The mainly evolved gases in the second stage
(T = 601.77 K) can be identified by these characteristic absorption
bands: the CO2 (2300–2385, 667 cm1), the H2O (3562–3941
cm1), the terpy (the mC@N (1578 cm1), the mCAN (1236, 1293
cm1), in-plane c@CAH (771 cm1) and out-of-plane c@CAH (1055, Fig. 5. Solid-state emission (a) and excitation (b) spectra of complex 2.

1113 cm1)) [24], and the 2-Br-5-MOBA (the mCAH, masOCH3 and ms-
1
OCH3 (2812–3106 cm ), the mC@C (1179–1341 cm1) and the mC@O
1
(1749 cm )). Thus, we can draw conclusions that terpy had been 773.62, 881.94 and 941.53 K except that the difference of intensity
dissociated in the first stage and the gaseous products also contain of absorption band of CO2. The mainly evolved gases are identified
dissociated and not dissociated 2-Br-5-MOBA ligands [25]. As by the characteristic absorption: the CO2 (2252–2385, 667 cm1),
shown in Fig. 5, there is the similar absorption at temperature of the CO (2109, 2186 cm1) and the H2O (3552–3799 cm1).
 Q.-Q. Zhao et al. / Polyhedron 144 (2018) 1–5
3.5. Luminescent properties
The fluorescent property of the complex 2 was investigated. The
solid-state luminescent spectra of Tb (III) complex at room
temperature were shown in the Fig. 5. The excitation spectrum
was obtained by monitoring the emission of the Tb (III) complex
at 542 nm, and the excitation maxima was observed at 349 nm.
Four expected peaks are observed in the emission spectrum.
They are assigned to 5D4 ? 7F6 (488 nm), 5D4 ? 7F5 (542 nm),
5
D4 ? 7F4(584 nm), and 5D4 ? 7F3 (621 nm) [26]. The electric
dipole transition 5D4 ? 7F5 at 542 nm dominates the whole
emission spectrum, which is responsible for the green emission
from Tb (III) complex. There is a broad band between 234 and
398 nm in the excitation spectrum of Tb (III) complex, which
corresponds to the p ? p⁄ electronic transition of the organic
ligand. What’s more, the quantum yield of the Tb (III) complex is
78.3%. We can draw a conclusion that the 2-Br-5-MOHBA ligand
can effective sensitize the luminescence of rare earth ions
(‘‘antenna effect”), according to the emission spectra. In addition,
the Tb (III) complex appears to be promising candidates for the
application as green luminescent material.
4. Conclusions
In summary, three new mononuclear complexes have been
successfully synthesized and characterized. The complexes 1–3
are isostructural and eight-coordinated, which is different from
the binuclear structure of the previously reported complexes.
The pseudo binuclear units constituted by the mononuclear
molecular are stitched together via slightly offset p–p stacking
and O–H  Br hydrogen bonding interactions to form the 1D, 2D
supramolecular structures. The thermal decomposition mecha-
nism for title complexes was obtained by TG and TG/DSC-FTIR
technology. The thermal stability of the three complexes is not
very good due to the presence of coordination water molecules.
The fluorescent spectra indicate that Tb (III) complex appears to
be promising candidate for the application as green luminescent
material.
Acknowledgements
The research work was supported by the National Natura
Science Foundation of China (no. 21473049) and the Natural
Science Foundation of Hebei Province (no. B2016205207).
5
Appendix A. Supplementary data
CCDC 1542527, 1542529 and 1542530 contains the supplemen-
tary crystallographic data for 1–3. These data can be obtained free
of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, or
from the Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail:
deposit@ccdc.cam.ac.uk. Supplementary data associated with this
article can be found, in the online version, at https://doi.org/10.
1016/j.poly.2017.12.036.
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