3-fold-interpenetrated uranium-organic frameworks: New strategy for rationally constructing three-dimensional uranyl organic materials

Article abstract of DOI:10.1021/ic202577z

The first series of 3-fold-interpenetrated uranium-organic frameworks, UOF-1 and UOF-2, have been synthesized by hydrothermal reactions of flexible semirigid carboxylic acids and uranyl nitrate. Structure analyses indicate that UOF-1 and UOF-2 possess flu

Full text of DOI:10.1021/ic202577z

Article
pubs.acs.org/IC
3-Fold-Interpenetrated Uranium−Organic Frameworks:
New Strategy for Rationally Constructing Three-Dimensional
Uranyl Organic Materials
Hong-Yue Wu,†,‡ Run-Xue Wang,† Weiting Yang,† Jinlei Chen,† Zhong-Ming Sun,*,† Jun Li,§
and Hongjie Zhang†
†State Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences,
5625 Renmin Street, Changchun, Jilin 130022, China
‡School of Chemistry & Environmental Engineering, Changchun University of Science & Technology, Changchun 130022, China
§Department of Chemistry & Key Laboratory of Organic Optoelectronics and Molecular Engineering of Ministry of Education,
Tsinghua University, Beijing 100084, China
S
* Supporting Information
ABSTRACT: The first series of 3-fold-interpenetrated uranium−organic frameworks,
UOF-1 and UOF-2, have been synthesized by hydrothermal reactions of flexible semirigid
carboxylic acids and uranyl nitrate. Structure analyses indicate that UOF-1 and UOF-2
possess flu and pts topologies, respectively.
with a charge of 2+, namely, uranyl, leaving 4−6 coordination
sites in the equatorial plane, thus favoring the formation of 1D
or 2D structures. It is a challenging task to rationally design and
synthesize 3D UOFs, especially the interpenetrated structures.
One popular strategy to isolate 3D UOFs is introducing a
second functional group such as pyridine or a carboxylate-
containing moiety into the ligands, thus leaving the potential
for further incorporating heterometal ions as structure-directing
agents.11a,f Another approach is using soft aliphatic carboxylic
acids or arylcarboxylic acids with strong hindrance to cross-link
the inorganic uranyl moieties to form 3D networks.11g,12
In most cases, however, it is noteworthy that linear aliphatic
carboxylic acids usually form chains or sheets with uranyl
cations.13 Apart from the methods mentioned above, reaction
conditions such as temperature, concentration, pH values, etc.,
also play significant roles in the assembly of 3D uranyl
compounds.7,14 In this paper, we describe a new strategy using
semirigid carboxylic acids as organic building blocks to
rationally synthesize the first examples of 3D UOFs with 3-
fold-interpenetrated networks.
INTRODUCTION
■
Metal−organic frameworks (MOFs) have attracted increasing
attention because of their remarkable potential applications in
gas storage,1 adsorption and separation,2 catalysis,3 molecule
and ion sensing,4 nonlinear optics,5a biomedical imaging, and
drug delivery.5b Interpenetrated three-dimensional (3D)
MOFs, compared with those low-dimensional analogies, are
of particular interest because of their privilege properties,
intriguing versatile architectures, and new topologies.6 In
contrast to the huge amount of transition-metal organic frame-
works, 5f actinide compounds that adopt various topologies
and coordination geometries have been less investigated.7−11
Uranium, as the most representative actinide element, has been
mostly investigated owing to its advantages in synthetic
methods, structure diversities, and physicochemical properties
for elements involved in the nuclear fuel cycle. So far, a number
of typical uranium compounds with various structures have
been synthesized,9−11 such as clusters,9 chains, layers, and 3D
networks.10,11 Among these structures, of significance are the
3D uranium−organic frameworks (UOFs) because of their
superior thermal stability to one-dimensional (1D) or two-
dimensional (2D) structures and outstanding properties such as
photoelectronic effects,11a nonlinear optical properties,11d and
porous adsorption.11f
EXPERIMENTAL SECTION
■
Caution! Standard procedures for handling radioactive material should be
followed, although the uranyl nitrate hexahydrate UO2(NO3)2·6H2O used
in the laboratory contained depleted uranium.
In contrast to the low-dimensional compounds, even
including cage clusters, the formation of 3D UOFs has proven
to be less successful.7,11 To the best of our knowledge, inter-
penetrated 3D UOFs have never been documented. The reason
is that UVI usually exists in the form of a linear OUO chain
Received: November 30, 2011
Published: February 10, 2012
© 2012 American Chemical Society
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Materials and Synthesis. All chemicals were purchased
commercially and used without further purification: uranyl nitrate
(99.8%, Sinpharm Chemical Reagent Co. Ltd.), K2CO3, and N,N-
dimethylformamide (DMF; 99.5%, Jinan Henghua Sci. & Tech. Co. Ltd.).
Trimethylolpropane tosylate (C3-OTs) and dipentaerythrityl hexato-
sylate (C6-OTs) were synthesized according to the literature.15 1H and
13C NMR spectra were carried out in a dimethyl sulfoxide (DMSO)-d6
initial pH 3.0; final pH 2.3. Yield: 102 mg (56% based on uranium).
Energy-dispersive X-ray analysis of several crystals showed the
presence of uranium. Elem anal. Obsd (calcd): C, 34.65 (34.49); H,
2.31 (2.23).
X-ray Crystal Structure Determination. Suitable single crystals
with dimensions of 0.24 × 0.32 × 0.08 mm3 for 1 and 0.18 × 0.26 ×
0.06 mm3 for 2 were selected for single-crystal X-ray diffraction
analyses. Crystallographic data were collected at 293 K on a Bruker
Apex II CCD diffractometer with graphite-monochromated Mo Kα
radiation (λ = 0.710 73 Å). Data processing was accomplished with the
SAINT program. The structures were solved by direct methods and
refined on F2 by full-matrix least squares using SHELXTL-97.17 Non-
hydrogen atoms were refined with anisotropic displacement
parameters during the final cycles. All hydrogen atoms of the organic
molecule were placed by geometrical considerations and were added
to the structure factor calculation. A summary of the crystallographic
data for these two complexes is listed in Table 1. Selected bond
distances and angles are given in Tables 2 and 3.
solvent on a Bruker 400 or 300 MHz spectrometer at 298 K.
The chemical shifts are given in dimensionless δ values and are
referenced relative to tetramethylsilane in 1H and 13C NMR
spectroscopy. Elemental analyses of carbon, hydrogen, and nitrogen
in the solid samples were performed with a VarioEL analyzer. Energy-
dispersive spectroscopy spectra were obtained by using a scanning
electron microscope (Hitachi S-4800) equipped with a Bruker AXS
XFlash detector 4010. All IR measurements were obtained using a
Bruker TENSOR 27 Fourier transform infrared spectrometer. Samples
were diluted with spectroscopic KBr and pressed into a pellet. Scans
were run over the range 400−4000 cm−1. The fluorescence spectra
were performed on a Horiba-Jobin Yvon Fluorolog-3 fluorescence
spectrophotometer, equipped with a 450 W xenon lamp as the
excitation source and a monochromator iHR320 equipped with a
liquid-nitrogen-cooled R5509-72 photomultiplier tube as the detector.
Synthesis of 4,4′-[[2-[(4-Carboxyphenoxy)ethyl]-2-methylpro-
pane-1,3-diyl]dioxy]dibenzoic Acid (H3L1). The ligand was synthe-
sized by a modified procedure.15,16 A mixture of C3-OTs (2.00 g, 3.35
mmol), ethylparaben (2.30 g, 13.74 mmol), K2CO3 (1.18 g, 8.60
mmol), and 20 mL of DMF was placed in a 100-mL round-bottomed
flask equipped with a magnetic stirbar. The reaction mixture was
refluxed for 16 h and then cooled to room temperature. After
quenching of H2O (100 mL), the product was extracted by ethyl
acetate (15 mL × 3). The volatile solvent was removed under vacuum;
after chromatographic separation, to the residue was added KOH
(3.85 g, 68.7 mmol), acetone (15 mL), and H2O (25 mL), and the
resulting misxture was then refluxed for 12 h. The mixture was diluted
with H2O (200 mL) and acidified by a 6 M HCl solution to pH ∼ 2.0.
A white solid was precipitated and filtered. The solid was dried under
vacuum. Yield: 1.21 g (2.45 mmol, 73%). 1H NMR (400 MHz,
DMSO-d6): δ 12.61 (br s, 3H), 8.87 (d, J = 8.8 Hz, 6H), 7.04 (d, J =
8.8 Hz, 6H), 4.17 (s, 6H), 1.75 (m, 2H), 0.934 (t, J = 7.2 Hz, 3H). 13C
NMR (100 MHz, DMSO-d6): 166.9, 162.1, 131.3, 123.2, 114.4, 67.7,
42.2, 22.6, 7.5. Elem anal. Obsd (calcd): C, 65.16 (65.58); H, 5.41
(5.30).
RESULTS AND DISCUSSION
■
In our understanding, ligands with flexible backbones com-
bining rigid multicoordination sites are good building blocks to
Table 1. Crystallographic Data for UOF-1 and UOF-2
UOF-1
762.49
UOF-2
1810.93
C2/c (No. 15)
fw
space group
a/Å
26.1023(19)
9.6889(7)
23.6885(17)
93.1170(10)
5982.0(7)
8
35.621(3)
9.2925(8)
20.4260(17)
114.6560(10)
6144.7(9)
4
b/Å
c/Å
β/deg
V/Å3
Z
T/K
293(2)
λ(Mo Kα)/Å
ρcalcd/(g cm−3
0.710 73
)
1.693
1.958
μ(Mo Kα)/mm−1
5.481
7.968
GOF
1.015
1.047
a
R1/wR2 [I > 2σ(I)]
R1/wR2 (all data)
0.0347/0.0687
0.0600/0.0758
0.0468/0.1275
0.0799/0.1496
Synthesis of Hexakis[4-(carboxyphenyl)oxamethyl]-3-oxapen-
tane (H6L2). Following a procedure similar to that of H3L1, C6-OTs
(2.00 g, 1.70 mmol), ethylparaben (2.26 g, 13.6 mmol), and K2CO3
(0.94 g, 6.80 mmol) in 20 mL of DMF were refluxed for 12 h. KOH
(3.81 g, 68.0 mmol), acetone (15 mL), and H2O (25 mL) were added,
and the resulting mixture was refluxed for 12 h in the second step.
Workup gave H6L2 as a white solid. Yield: 1.16 g (1.19 mmol, 70%).
1H NMR (300 MHz, DMSO-d6): δ 12.40 (br s, 6H), 7.84 (d, J = 9.0
a
R1 = ∑||Fo| − |Fc||/∑|Fo|, wR2 = {∑w[(Fo)2 − (Fc)2]2/
∑w[(Fo)2]2}1/2
.
Table 2. Selected Bond Lengths and Bond Angles for
a
UOF-1
Hz, 12H), 6.95 (d, J = 9.0 Hz, 12H), 4.21 (s, 12H), 3.75 (s, 4H). 13C
NMR (75 MHz, DMSO-d6): 167.4, 162.4, 131.7, 123.9, 114.7, 69.8,
67.1, 40.0 (m). Elem anal. Obsd (calcd): C, 64.39 (64.06); H, 4.37
(4.76).
U1−O1
1.722(4)
2.283(3)
2.428(4)
2.468(3)
U1−O2
U1−O3
U1−O8#3
1.741(4)
2.310(3)
2.443(4)
U1−O4#1
U1−O5#2
U1−O7#3
UO2(HL1) (UOF-1). The title compound was prepared by a
hydrothermal method. A mixture of 0.1 M UO2(NO3)3 aqueous
solution (1.0 mL, 0.100 mmol), H3L1 (57 mg, 0.1 mmol), and
deionized water (5 mL, 278 mmol) was loaded into a 20-mL Teflon-
lined stainless steel autoclave. The autoclave was sealed and heated at
180 °C for 3 days and then cooled to room temperature. Yellow
crystals were isolated: initial pH 3.0; final pH 2.5. Yield: 42 mg (63%
based on uranium). Energy-dispersive X-ray analysis of several crystals
showed the presence of uranium. Elem anal. Obsd (calcd): C, 42.78
(42.53); H, 3.35 (3.17).
O1−U1−O2
179.24(17)
90.56(15)
89.85(16)
89.08(15)
91.58(16)
85.35(12)
88.72(16)
91.08(17)
162.12(12)
76.77(12)
90.31(16)
O2−U1−O8#3
O4#1−U1−O8#3
O3−U1−O8#3
O5#2−U1−O8#3
O1−U1−O7#3
O2−U1−O7#3
O4#1−U1−O7#3
O3−U1−O7#3
O5#2−U1−O7#3
O8#3−U1−O7#3
88.94(17)
128.94(12)
145.71(12)
68.94(12)
88.58(15)
90.90(16)
76.54(12)
161.71(12)
121.30(12)
52.45(12)
O1−U1−O4#1
O2−U1−O4#1
O1−U1−O3
O2−U1−O3
O4#1−U1−O3
O1−U1−O5#2
O2−U1−O5#2
O4#1−U1−O5#2
O3−U1−O5#2
O1−U1−O8#3
(UO2)3(H2O)2L2 (UOF-2). To a 20-mL Teflon-lined stainless steel
autoclave was added 0.1 M UO2(NO3)3 aqueous solution (1.0 mL,
0.10 mmol), H6L2 (60 mg, 0.062 mmol), and deionized water (5 mL,
278 mmol). The mixture was heated at 180 °C for 7 days and then
cooled to room temperature. Yellow platelets of the title compound
suitable for single-crystal X-ray diffraction studies were isolated:
a
Symmetry code: #1, −x + 1, −y − 1, −z; #2, −x + 1, y, −z + 1/2; #3,
1
3
x − /2, y − /2, z.
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Table 3. Selected Bond Lengths and Bond Angles for
a
UOF-2
U1−O12
U1−O8
U1−O6#2
U1−O1W
U2−O10#1
1.689(10)
2.297(7)
2.426(8)
2.462(9)
2.276(8)
U1−O11
U1−O9#1
U1−O5#2
U2−O13
U2−O7
1.746(8)
2.317(7)
2.427(8)
1.739(8)
2.287(7)
O12−U1−O11
O12−U1−O8
O11−U1−O8
178.8(5)
90.2(4)
91.0(3)
90.9(4)
89.4(3)
84.9(3)
90.6(4)
89.5(4)
77.2(3)
162.0(3)
89.3(4)
89.8(4)
130.2(3)
144.9(3)
53.0(3)
O12−U1−O1W
O11−U1−O1W
O8−U1−O1W
O9#1−U1−O1W
O6#2−U1−O1W
O5#2−U1−O1W
O13−U2−O13#3
O13−U2−O10#1
O10#1−U2−O10#4
O13−U2−O7
89.1(5)
89.8(4)
161.0(3)
76.2(3)
121.8(3)
68.8(3)
180.0
O12−U1−O9#1
O11−U1−O9#1
O8−U1−O9#1
O12−U1−O6#2
O11−U1−O6#2
O8−U1−O6#2
O9#1−U1−O6#2
O12−U1−O5#2
O11−U1−O5#2
O8−U1−O5#2
O9#1−U1−O5#2
O6#2−U1−O5#2
90.0(4)
180.0
88.3(4)
91.7(4)
89.0(3)
91.0(3)
180.0(2)
O13#3−U2−O7
O10#1−U2−O7
O10#4−U2−O7
O7−U2−O7#3
a
Symmetry code: #1, x, −y, z + 1/2; #2, −x + 1/2, −y + 3/2, −z + 2; #3,
−x, −y, −z + 2; #4, −x, y, −z + /2.
3
Figure 1. ORTEP representation of the asymmetric units of UOF-1
(a) and UOF-2 (b). Thermal ellipsoids are drawn at the 30%
probability level, and the hydrogen atoms are omitted for clarity.
Symmetry codes for UOF-1: A, 0.5 − x, 0.5 + y, 0.5 − z. Symmetry
codes for UOF-2: A, 0.5 + x, 0.5 + y, z; B, 0.5 − x, 0.5 + y, 0.5 − z; C,
0.5 + x, 0.5 − y, −0.5 + z.
construct new 3D uranyl coordination polymers. On the basis
of this point, semirigid carboxylic acids H3L1 and H6L2
(Scheme 1) are adopted in this work, clearly their versatile
Scheme 1. Structures of Ligands H3L1 and H6L2
and 1.746(8) Å], four planar μ2-oxygen atoms from three L2
ligands [U−O, 2.297(7)−2.427(8) Å], and one aqua ligand
[U−O, 2.462(9) Å], while the U2 atom is octahedrally
coordinated to four μ2-oxygen atoms shared with four adjacent
carboxylate groups from four L2 ligands [U−O, 2.276(8)−
2.287(7) Å], leaving two axial oxygen atoms to form a uranyl
unit [OUO, 180°; UO, 1.739(8) Å]. These values are
within the typical bond length ranges reported for uranium-
containing materials. Selected bond lengths and angles are
listed in Tables 2 and 3.
The most striking features of UOF-1 and UOF-2 are the
connections between UO2 and the ligands to form 3D inter-
coordination directions in space make the design and pre-
diction of the 3D networks possible. Hydrothermal reactions of
H3L1, H6L2, and UO2(NO3)2·6H2O at 180 °C resulted in
compounds UOF-1 and UOF-2, respectively. Single-crystal
X-ray diffraction studies indicate that both compounds adopt
the same monoclinic space group C2/c but are not isostructural
(Table 1).
As shown in Figure 1a, the asymmetric unit of UOF-1
consists of one uranyl unit and one protonated L1 ligand. The
uranium atom is seven-coordinated by oxygen atoms, resulting
in a pentagonal bipyramid as the primary building unit. Axially,
the OUO angle is 179.24(17)°, and the UO lengths are
1.722(4) and 1.741(4) Å. Equatorially, the uranium atom is
five-coordinated to μ2-oxygen atoms from the carboxylate
groups of three L1 ligands [U−O, 2.283(3)−2.468(3) Å]. In
order to keep a charge balance, L1 is protonated at the O6 site
[C14−O6, 1.320(6) Å]. The asymmetric unit of UOF-2
(Figure 1b) contains one and a half crystallographically inde-
pendent uranyl units and half of a L2 ligand. The U1 atom exists
in the form of a UO7 pentagonal bipyramid including two linear
uranyl oxygen atoms [OUO, 178.8(5)°; UO, 1.689(10)
2+
penetrated networks. In UOF-1, the structure adopts a dimeric
uranyl unit as its secondary building unit (SBU; Figure 2a), which
is further linked by L1 to form a 3D network with large
parallelogram channels along the ⟨111⟩ direction, in which the
diagonal lengths are around 20.2 and 35.5 Å and the bent angle
is 58.5°. Similarly, the single net in UOF-2 also exhibits a
porous 3D framework with large channels but adopts trimeric
uranyl units (including one square bipyramid and two
pentagonal bipyramids) as its SBUs (Figure 2b). The diagonal
lengths within the channels are around 20.4 and 34.8 Å and the
bent angle is 60.5°. Because of the large void volume of the
single nets in UOF-1 and UOF-2, triple equivalent networks
interpenetrate each other to keep their stabilities of the whole
structure. The space-filling models in Figure 3 clearly display
this feature; each net is represented by a unique color, including
red, green, and blue. Simplified interpenetrating srtuctures are
shown in Figure 4. On the basis of the calculations using the
PLATON program,18 the total potential solvent-accessible void
volumes (pore volume ratio) per unit cell are ∼801.6 Å3
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Figure 4. Simplified 3-fold-interpenetrated networks of UOF-1 (a)
and UOF-2 (c) colored separately in red, green, and blue. Topological
presentations of UOF-1 (b) and UOF-2 (d).
form the framework. As a result, the underlying topology of the
compound is a 4-connected net with both the center of the
uranyl SBU and the center of the L2 unit as nodes. Topological
analysis indicates that UOF-2 adopts a pts net with a Schlfli
symbol of (42.84) (Figure 4d).
The IR spectra of UOF-1, UOF-2, H3L1, and H6L2 are
shown in Figure 5. The spectra of UOF-1 and UOF-2 exhibit
Figure 2. Single net views of UOF-1 (a) and UOF-2 (b). The SBUs
are shown on the bottom left.
Figure 3. Space-filling model of 3D networks in UOF-1 (a) and UOF-2
(b). The nets are depicted by different colors: red, green, and blue.
Figure 5. IR spectra of UOF-1, UOF-2, and the ligands H3L1 and
H6L2.
(13.4%) and 1020.0 Å3 (16.6%) for UOF-1 and UOF-2,
respectively.
additional vibrational peaks around 950 and 880 cm−1 com-
pared to the ligands, which are attributed to the asymmetric and
symmetric UO vibrations, respectively (934 and 878 cm−1
for UOF-1; 954 and 878 cm−1 for UOF-2). In UOF-2, the
stretching vibration of the coordinated H2O molecule is clearly
indicated on a broad band centered at 3448 cm−1.
The photoluminescent properties of UOF-1 and UOF-2
were characterized, and only emission of the ligands was
observed instead of the characteristic emission features of
UO22+. This implies that the UO22+-centered luminescence is
poorly sensitized by the ligands.
To further understand the complicated structures, topo-
logical analyses were employed.19 In UOF-1, every uranyl SBU
is surrounded by six L1 units, and each L1 linker connects three
uranyl SBUs to form a 3D framework. The uranyl
SBU and L1 ligand can be considered as 6- and 3-connected
nodes, respectively. Thus, UOF-1 can be represented as a 3,6-
connected 3-fold-interpenetrating net with a Schlafli symbol of
(42.6)2(44.62.87.102) and flu-3,6-C2/c topology (Figure 4b).
Accordingly, every uranyl SBU in UOF-2 is surrounded by four
L2 ligands, and each L2 linker also connects four uranyl SBUs to
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In conclusion, two new 3D uranium organic frameworks
have been hydrothermally synthesized using uranyl cations and
semirigid carboxylic acids with flexible backbones; both
compounds feature 3-fold-interpenetrated structures. This
method provides a new strategy to rationally design and
synthesize new uranium−organic compounds. Future work will
be focused on the syntheses of further extended structures of 3D
UOFs using secondary ligands, which may result in micro/
mesoporous materials with potential applications in gas
separation or absorption.
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ASSOCIATED CONTENT
* Supporting Information
X-ray crystallographic CIF file. This material is available free of
charge via the Internet at http://pubs.acs.org.
■
S
(15) Keegstra, E. M. D.; Zwikker, J. W.; Roest, M. R.; Jenneskens,
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AUTHOR INFORMATION
Corresponding Author
*E-mail: szm@ciac.jl.cn.
Notes
■
(16) (a) Wang, Y. W.; Zhang, Y. L.; Dou, W.; Zhang, A. J.; Qin,
W. W.; Liu, W. S. Dalton Trans. 2010, 39, 9013. (b) Laliberte, D.;
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The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(18) Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.
This work was supported by the National Nature Science
Foundation of China (Grant 21171662) and CIAC startup
fund. W.Y. is thankful for support of the China Postdoctoral
Science Foundation (CPSF No. 20110491327).
(19) (a) Blatov, V. A.; Shevchenko, A. P.; Serezhkin, V. N. Acta
Crystallogr., Sect. A 1995, 51, 909. (b) Blatov, V. A.; Carlucci, L.; Ciani,
G.; Proserpio, D. M. CrystEngComm 2004, 6, 378.
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