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Instituto de Fsica de Sao Carlos, Universidade de Sao Paulo, CP 369, 13560-970 Sao Carlos, Sao Paulo, Brasil
Laboratorio de Modelagem ComputacionalLaModel, Instituto de Ciencias Exatas, Universidade Federal de AlfenasUnifal-MG,
37130-000 Alfenas, Minas Gerais, Brazil
S Supporting Information
*
INTRODUCTION
Since the appearance of metalorganic frameworks
(MOFs),13 several types of connectors (metallic centers)
and linkers (organic ligands) have been used in their design, in
search of new compounds with new architectures, topologies,
and interesting properties.410 Lanthanide metals exhibit
properties that make them excellent candidates for the
synthesis of new MOFs. Lanthanides have electrons in f
orbital, which enables them to generate ff transitions when
interacting with the appropriated radiation.6 Due to the
electronic nature of these metals and high positive charge,
they show high Lewis acidity.1113 The lanthanide inuence on
MOF structure can be applied to the manufacture of materials
with luminescent or electroluminescent properties, materials for
telecommunications, and light-emitting diodes, heterogeneous
catalysis, magnetic devices, sensors, and contrast agents.1421
Moreover, the selection of linkers in the MOF design depends
on two types of factors: (i) structural factors, such as exibility
or stiness, coordination modes, connectivity, and size, among
others, and (ii) functional factors, such as aromatic rings,
functional groups, and electronic delocalization. Succinic acid is
a exible linker that has the ability to have dierent
coordination modes. Therefore, dierent phases or structural
isomers of general formula [Ho2(C4H4O4)3(H2O)n](H2O)m
have been synthesized.2232
This paper reports a synthetic study of the Ln/succinate
system for obtaining Ln-based MOFs using organic templates
as reaction drivers.33 Also, the formation equilibrium and the
thermodynamical stability of the crystal phases and its eect on
XXXX American Chemical Society
EXPERIMENTAL SECTION
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
Table 1. Crystallographic and Renement Data for Compounds [La2(Succ)3(H2O)3]2H2O and [Ln2(Succ)3(H2O)2] Obtained
by Two Dierent Methodologies
Methodology 1
[La2(Succ)3(H2O)3]2H2O
emp formula
FW (g/mol)
temp (K)
()
cryst. syst.
space group
unit cell
a ()
b ()
c ()
(deg)
(deg)
(deg)
vol (3)
Z
calcd (mg/m3)
abs coe (mm1)
F(000)
range (deg)
rens collected/unique [R(int)]
completeness (%)
Data/restraints/params
GOF on F2
R1 [I > 2(I)]
wR2[I > 2(I)]
[La2(Succ)3(H2O)2]
C12H22O17La2
716.12
298
0.71073
orthorhombic
Pbnm
emp formula
FW (g/mol)
temp (K)
()
cryst syst
space group
unit cell
a ()
b ()
c ()
(deg)
(deg)
(deg)
vol (3)
Z
calcd (mg/m3)
abs coe (mm1)
F(000)
range (deg)
rens collected/unique [R(int)]
completeness (%)
data/restraints/params
GOF on F2
R1 [I > 2(I)]
wR2 [I > 2(I)]
C12H16O14La2
662.07
298
0.71073
triclinic
P1
10.2108(5)
13.7312(7)
14.7406(9)
90
90
90
2066.7(2)
4
2.302
4.162
1376
2.926.4
4020/2197 [0.034]
99.9
2197/0/154
1.079
0.0412
0.0927
Methodology 2
7.976(8)
12.006(1)
12.284(1)
112.01(2)
90.05(3)
100.58(5)
1068.9(2)
2
2.057
4.005
628
2.926.4
14114/5027 [0.076]
98.4
5027/0/255
0.944
0.0532
0.1674
[La2(Succ)3(H2O)2]
[Pr2(Succ)3(H2O)2]
[Nd2(Succ)3(H2O)2]
298
0.71073
triclinic
P1
7.979(2)
12.095(3)
12.297(4)
111.68(1)
89.93(2)
100.16(2)
1082.8(5)
2
2.018
3.953
620
3.026.4
31102/4384 [0.097]
99.3
4384/0/255
0.82
0.0393
0.0991
7.877(1)
12.060(3)
12.275(1)
112.12(4)
89.98(3)
99.95(5)
1061.0(3)
2
2.7079
4.600
632
2.926.3
30410/4310 [0.137]
99.7
4310/0/250
1.501
0.1219
0.3637
7.8354(7)
12.0496(2)
12.2524(2)
112.015(5)
89.967(7)
99.921(7)
1053.8(2)
2
2.107
4.935
632
3.026.6
26997/4179 [0.214]
94.8
4179/0/243
0.969
0.0844
0.2392
7.7050(3)
11.9893(7)
12.1828(6)
112.143(2)
89.979(3)
99.580(3)
1025.48(9)
2
2.263
6.592
656
3.026.2
7825/4063 [0.053]
98.9
4063/0/232
1.12
0.1365
0.3801
[Gd2(Succ)3(H2O)2]
C12 H16 O14 Gd2
room temperature for 30 min. The mixture was then placed into
Teon-lined stainless steel autoclaves for reaction under hydrothermal
conditions. After cooling to room temperature, the crystalline products
were ltered and washed with water and acetone.
[La2(Succ)3(H2O)3]2H2O (phase 1) was obtained as a mixture
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
Figure 1. ORTEP diagram with 50% probability for compounds (a) [La2(Succ)3(H2O)2] and (b) [La2(Succ)3(H2O)3]2H2O. Hydrogen atoms were
removed for clarity, and only the atoms present in the asymmetric unit were labeled.
with a small amount of [La2(Succ)3(H2O)2] (phase 2) when the
reaction was heated to 160 C for 18 h. When the temperature was
increased to 170200 C, compound [La2(Succ)3(H2O)2] appeared
as the main reaction product (yield 42.38%), with small amounts of
the previously reported compounds [La2(Succ)3(H2O)2]2H2O
(phase 3)29 and [Ln2(Succ)2(SO4)(H2O)2] (phase 4 = RPF-16La). 3 4 Elemental Anal. Calcd for [La 2 (Succ) 3 (H 2 O) 2 ]
(C12H16O17La2): C, 21.7; H, 2.4. Found: C, 21.22; H, 3.1.
Methodology 2. The molar composition of the initial reaction
mixture in all cases was set as succinate2/Ln3+/1474H2O/250toluene.
Succinic acid (0.013 g, 0.115 mmol) was added to a solution of
La(NO3)36H2O (0.05 g, 0.115 mmol) in 3 mL of water; the reaction
mixture was adjusted to pH 4.4 by the addition of NaOH (1 M)
under constant stirring at room temperature for 30 min. Finally, 3 mL
of toluene was added to the reaction mixture, and the mixture was
placed into Teon-lined stainless steel autoclaves for reaction under
hydrothermal conditions at 200 C. After cooling to room temperature, the crystalline products were ltered and washed with water and
acetone, and product was obtained in 78.01% yield. The same
procedure was followed for the synthesis of all compounds
[Ln2(Succ)3(H2O)2], where Ln = La, Pr, Nd, Sm, Eu, Gd, and Tb.
Elemental Anal. Calcd for [La2 (Succ) 3 (H2 O) 2 ]0.33(toluene)
[(C12H16O17La2)0.33(toluene)]: C, 22.84; H, 2.46. Found: C,
23.56; H, 2.93. Anal. Calcd for (C12H16O17Pr2)0.33(toluene): C,
22.72; H, 2.45. Found: C, 23.31; H, 2.82. Anal. Calcd for
(C12H16O17Nd2)0.33(toluene): C, 22.52 ; H, 2.43. Found: C, 23.90;
H, 3.17. Anal. Calcd for (C12H16O17Gd2)0.5(toluene): C, 22.93; H,
2.44; found: C, 23.46; H, 3.05.
Single-Crystal Structure Determination. Single-crystal X-ray
data for all the compounds were collected at room temperature (298
K) on an Enraf-Nonius Kappa-CCD diractometer using Mo K
radiation (0.71073 ) monochromated by graphite. The cell was
rened by Collect and Scalepack software, and the nal cell parameters
were obtained on all reections. A data reduction was carried out using
Denzo-SMN and Scalepack software.35 The structure was solved by
SHELXS-2013 software and then rened by SHELXL-2013,36
included in WinGX37 and Olex2.38 Non-hydrogen atoms of the
molecules were clearly resolved, and the full-matrix least-squares
renement of these atoms, with anisotropic thermal parameters, was
carried out. All hydrogen atoms were stereochemically positioned and
rened with the riding model.36 Hydrogen atoms of the water
molecules were localized in the density map and xed (with Uiso(H) =
1.5Ueq). ORTEP diagram was prepared with Diamond.39 TOPOS,40
Mercury,41 and Diamond39 programs were used in the preparation of
the artwork of the polyhedral and topological representations.
X-ray Powder Diraction. PXRD patterns were measured with a
Rigaku Ultima IV diractometer of 0.02 step size and 2 s/step
exposure time. PXRD measurements were used to prove the
isostructurality of the series and check the purity of the obtained
microcrystalline products through the comparison of the experimental
results with the simulated pattern obtained from single crystal X-ray
diraction data.
Computational Details. To study the structural and electronic
properties of the solid phase, the calculations were performed
considering the density functional theory (DFT) for periodical
systems methodology.42,43 DFT was used as implemented in the
SIESTA code,44 and the generalized gradient approximation (GGA)
was employed for the exchange-correlation potential using the PBE
scheme.45 To avoid the need for explicit treatment of the core
electrons, the norm-conserving TroullierMartins pseudopotentials46
were used. For the valence electrons, we used a split-valence double-
basis set with polarization functions (DZP).47 To obtain results
suciently accurate, convergence studies were done for the mesh
cuto energy and the number of k-points. The total energy
convergence for the systems was obtained for a mesh cuto of 600
Ry and for a k-point set of 8 8 8. In the case of the La atom, we
used the nonlinear core corrections48 and the 5s2 and 5p6 semicore
states explicitly included in the calculations. The structure
optimizations were done until the HellmanFeynman forces were
below 0.01 eV/ and the energy convergence criterion was equal to
106. To calculate the lattice formation energy (Eform) of each phase,
we have to calculate the energy of the reagents (ER) and the energy of
the nal product (EP), that is, of the crystals. From these calculations,
the lattice formation energy is obtained as Eform = EP ER.49
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
Study of the Eect of Synthesis Conditions on the LnSuccinate Formation. Methodology 1. In order to study the
system succinate2/La3+/5-SSA3, the reaction stoichiometry
was xed as is shown in the Experimental Section. Several
experiments were conducted to nd the optimal reaction pH:
with pH values <4 no reaction product was observed. At pH
4, the new compounds (phases 1 and 2) were obtained as a
function of the temperature and reaction time, while with pH
values >5, the previously reported compounds (phases 3 and 4)
were observed as main reaction products. Once we found and
set up the reaction stoichiometry and pH, several variable
studies were performed: (i) First, it was found that with long
reaction time the reported phases 3 and 4 are obtained; for this
reason, the reaction time used ranged between 18 and 24 h. (ii)
Heating the reaction mixture between 140 and 160 C for 18 h
produced the compound [La2(Succ)3(H2O)3]2H2O (phase 1)
always as a mixture with phase 2 (Figure 8). (iii) When the
temperature was increased to values between 170 and 190 C
for 18 h of reaction, the compound [La2(Succ)3(H2O)2] (phase
2) was obtained with a small amount of phase 3. (iv) As
mentioned in the synthesis section, at temperatures above 190
C and long reaction times, mixtures of phase 4 with traces of
phase 2 are found (Figure 8).
Methodology 2. The next step of the synthetic study was to
test what happened when the organic molecule changed in the
reaction. Dierent aromatic molecules, namely, benzoic acid,
acetylsalycilic acid, aniline, toluene, 6-hydroxypicolinic acid, and
sulfate anion, were tested (Table 3). The template eect has
been extensively studied and demonstrated in several works.33
Templating by guests (TBG) consists of a guest molecule that
act as a template;33 this could be the case for the selected
molecules for this test (Table 3).
According to Table 3, in three cases the main product is
phase 3, which is thermodynamically more stable and whose
formation is favored. The presence of water molecules in the
cavities stabilize the structure through interactions with the
coordinated water molecules. In this case, the water acts as a
template to give rise to small channels.
Using 6-hydroxypicolinic acid, acetylsalycilic acid, and aniline
resulted in the formation of the compound [Ln(succ)(Oxal)0.5(H2O)2]H2O.55 This occurs possibly due to the
total decomposition of these molecules at high temperature
(200 C), which allows the formation of oxalate anion.
Finally, in the presence of toluene, the formation of phase 2
is almost total, which suggests that toluene can be a template
giving structural support to the MOF formation. The toluene
template shifts the formation equilibrium to phase 2 and acts as
a support changing the formation energy and mechanism.
Theoretical Stability Studies. The crystal structural
stability study was performed through the lattice geometry
optimization calculations of the reaction products obtained
under synthesis methodology 1 (phases 1, 2, 3, and 4). These
calculations were carried out in three dierent approaches using
as the initial geometry the single-crystal X-ray structures (see
Experimental Section for details). In the rst approach, only the
atom positions were optimized. In the second approach, the cell
parameters together with the atoms positions were optimized at
a xed volume. Finally, in the third approach, a full cell
optimization was performed without any constraints. Our
results are summarized in Table 4.
The results in Table 4 indicate that the crystal structures
correspond to the more stable structures. This is based on the
fact that the calculated crystal energies are very similar, even
Figure 6. Crystal void and void surface (0.002 au) for compound
[La2(Succ)3(H2O)2] (crystal voids calculate with CrystalExplorer).53
space
group
[La2(Succ)3(H2O)2]
[La2(Succ)3(H2O)2]b
[Pr2(Succ)3(H2O)2]b
[Nd2(Succ)3(H2O)2]b
[Gd2(Succ)3(H2O)2]b
[La2(Succ)3(H2O)3]2H2O
[Ce2(Succ)3(H2O)2]54
[La2(Succ)3(H2O)2]H2O
(phase 3)29
[Ho2(Succ)3(H2O)2]24
[Ho2(Succ)3(H2O)2]
0.33(C7H6O3)24
[Sm2(2,2dimethylSucc)3(H2O)2]21
[Ln2(Succ)2(SO4)(H2O)2]
(phase 4)34
P1
P1
P1
C2/c
P1
P1
P1
P21/n
(20.6%)
(23.5%)
(22.2%)
(23.5%)
(20.0%)
(10.3%)
(8.5%)
102.9 (12.0%)
215 (21.5%)
topology
bnn
sql
3,4T1
fsc
pcu
bnn
52.5(4.6%)
bnn
125.6 (8.2%)
pcu
a
Synthesized under methodology 1. bSynthesized under methodology
2. cNo void space.
(solvent accessible volume) of dierent lanthanide/succinatebased compounds, and the synthesized [Ln2(Succ)3(H2O)2]
MOF shows the largest solvent accessibility relative value found
until now (Section S6, Supporting Information, shows a wide
search in CCDC of Ln/succinate compounds).
Making a simplied model of the 3D network is made
possible by rod-packing construction.51 It could be observed
that the intermetallic centroid may act as a 5-connected node
(Figure 7), while the succinate anions link this node give rise to
a 5-connected network type bnn with point symbol (4664).40
E
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
Figure 7. Polyhedral representation and topological simplication of the bnn network of compound [Ln2(Succ)3(H2O)2].
Figure 8. (a) Scheme of the reaction and crystalline products and (b)
scanning reaction conditions for the succinate2/LaIII/5-SSA3 system.
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
Table 3. Summary of the Templates and Reaction Conditions Studied in This Work
Reference 55.
1
2
3
4
energya
energyb
energyc
10337.883504
12353.424257
5750.462236
47824.996056
10337.817257
12353.492220
5750.654977
47824.703158
10337.848130
12354.506532
5750.654977
47824.564723
Figure 10. IR spectra for the dierent phases found in the La/succ/5SSA3 reaction.
CONCLUSION
This study has addressed the synthesis and characterization of a
new La/succinate-based 2D compound named phase 1, whose
G
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
Figure 11. Room-temperature emission spectra of compounds (a) [Eu2(Succ)3(H2O)2], (b) [Tb2(Succ)3(H2O)2], and (c) [Sm2(Succ)3(H2O)2]
excited to 280 nm.
AUTHOR INFORMATION
Corresponding Author
ACKNOWLEDGMENTS
R.D. acknowledges Coordenacao de Aperfeicoamento de
Pessoal de Nivel Superior for the CAPES/PNPD scholarship
from the Brazilian Ministry of Education, the Crystallography
Group of IFSC-USP, and M.J. Davila from UFSCAR and E.C.
Muniz from UNESP for the spectroscopic analysis. I.C.
acknowledges Brazilian agency FAPEMIG for the nancial
support. J.E. thanks CNPq for research fellowships.
ASSOCIATED CONTENT
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S Supporting Information
*
DOI: 10.1021/acs.cgd.5b00426
Cryst. Growth Des. XXXX, XXX, XXXXXX
Article
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DOI: 10.1021/acs.cgd.5b00426
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