Ultrahigh volatile iodine uptake by hollow microspheres formed from a heteropore covalent organic framework

Article abstract of DOI:10.1039/c7cc01045a

We herein report the construction of a new heteropore COF which consists of two different kinds of micropores with unprecedented shapes. It exists as hollow microspheres and exhibits an extremely high volatile iodine uptake (up to 481 wt%) by encapsulating iodine in the inner cavities and porous shells of the microspheres.

Full text of DOI:10.1039/c7cc01045a

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Reactivity differences of Sc
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Ultrahigh volatile iodine uptake by hollow microspheres formed
from a heteropore covalent organic framework
Received 00th January 20xx,
Accepted 00th January 20xx
a,b
a
a
a
b
a,*
Zhi-Jian Yin, Shun-Qi Xu, Tian-Guang Zhan, Qiao-Yan Qi, Zong-Quan Wu and Xin Zhao
DOI: 10.1039/x0xx00000x
www.rsc.org/
4
We herein report the construction of a new heteropore COF which 336 wt% was reported. Given their features of facile
consists of two different kinds of micropores with unprecedented syntheses, low densities, structural diversities, and
shapes. It exists as hollow microspheres and exhibits an extremely chemical/thermal stability, POPs are very promising candidates
high volatile iodine uptake (up to 481 wt %) by encapsulating for practical applications in capturing radioactive iodine from
iodine in the inner cavities and porous shells of the microspheres.
exhaust fumes of nuclear power plants. To reach this goal,
improving performance of POPs on iodine capture is highly
desired.
Global environmental problems resulted from combustion of
fossil fuels have become more and more serious over the past
decade. Compared with fossil fuels, nuclear power holds
ultrahigh energy density as well as emits fewer greenhouse
gases, and thus is gradually growing into one of the pillars of
energy sources around the world. However, disposal of the
inevitable nuclear waste generated from nuclear fission of
uranium still faces great challenges. In this regard, radionuclide
iodine-129 is one of the most dangerous waste products of
Among POPs, covalent organic frameworks (COFs)
distinguish themselves from the others by their highly ordered5
internal structures which endow them with crystallinities.
Compared to amorphous POPs, the pore shapes and sizes of
COFs can be precisely controlled through elaborate design of
building blocks, which makes them highly efficient for selective
6
7
8
storage, separation, sensing, or transportation of guest
9
molecules. However, to our surprise, while COFs have been
nuclear power plants because of its long radioactive half-life
extensively used for gas storage, so far the capacity of COFs on
iodine capture have not been examined yet. Very recently
7
(
1.57×10 years), high volatility, and adverse effects on human
1
10
11
metabolic processes and environment. In this context, great
efforts have long been focused on effective capture and
storage of radioactive iodine for safe utilization of nuclear
energy. The early adsorbents developed for iodine capture are
inorganic adsorbents, including silver-based zeolites and
we and others have developed a new class of COFs, that is,
heteropore COFs, which bear different kinds of pores in one
framework and thus endow them with hierarchical porosities.
Since hierarchical porous materials have been reported to be
12
favorable for transportation of guest molecules, heteropore
COFs, which combine the features of highly ordered internal
structures and hierarchical porosities, might be conducive to
iodine capture. We herein report a hollow spherical
heteropore COF (SIOC-COF-7) which greatly facilitates the
adsorption of volatile iodine. An iodine uptake of 481 wt % was
obtained. To the best of our knowledge, it is the first COF-base
iodine adsorbent and the highest iodine uptake value reported
to date.
2
aerogels. However, those inorganic adsorbents usually
exhibited low uptake capacities. In recent years, inorganic-
organic hybrid porous materials such as metal-organic
frameworks (MOFs) have also been exploited as iodine
capturing materials and moderate uptake capacities have been
3
achieved. More recently, porous organic polymers (POPs)
have been found to exhibit great potential for iodine capture
and storage, and among them a maximum iodine uptake up to
SIOC-COF-7 was synthesized as an orange powder by
condensation
1,1':4',1''-terphenyl]-2',5'-dicarbaldehyde (BFATD) and 1,4-
diaminobenzene in mixed solvent of
dioxane/mesitylene/acetic acid (aq., 6 M) (5:5:1 by volume) in
a sealed glass ampoule at 120 °C for 72 h (Scheme 1). The as-
of
4,4''-bis(bis(4-formylphenyl)amino)-
a.
CAS Key Laboratory of Synthetic and Self-Assembly Chemistry for Functional
[
Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences,
b.345 Lingling Road, Shanghai 200032, China. E-mail: xzhao@sioc.ac.cn
Department of Polymer Science and Engineering, School of Chemistry and
Chemical Engineering, Hefei University of Technology, Anhui Province, Hefei
a
2
30009, China.
†
Electronic Supplementary Information (ESI) available: Procedures for the prepared powder, which is insoluble in common organic
preparation of the monomer and COF, FTIR spectra, TGA profiles, additional TEM
images, photographs for iodine capture in solution, summary of iodine uptakes of
porous materials, and BET plot. See DOI: 10.1039/x0xx00000x
solvents and water, exhibits a high thermal stability. As
revealed by thermogravimetric analysis (TGA), less than 10%
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1
00
001
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DOI: 10.1039/C7CC01045A
a
b
2
-10
20 22 24 26
1
-20
1
-10 3-10
c
d
5
10
15
20
25
30
2
Theta
Fig. 1 Left: (a) Experimental (black) and refined (red) PXRD patterns of SIOC-COF-
. (b) Difference plot between the experimental and refined PXRD patterns. And
simulated PXRD patterns for (c) eclipsed AA model and (d) staggered AB model.
Right: Illustrations of AA and AB stackings.
7
a
300
Adsorption
Desorption
b 4000
11.8 Å
250
200
150
100
3
500
3000
2500
2000
1500
5.0 Å
Scheme 1. Synthesis and structure of the heteropore COF SIOC-COF-7
.
50
1000
500
0
0
weight loss was observed for the COF when the temperature
increased from 25 to 500 °C (Fig. S1, ESI). TEM investigation
indicated that the COF existed as hollow microspheres with
0.0
0.2
0.4
0.6
0.8
1.0
0
20
40
Relative Pressure (P/Po)
Pore Width (Angstrom)
2
Fig. 2 (a) N adsorption-desorption isotherm curve of SIOC-COF-7 at 77 K and (b)
diameters around one to two micrometers and shell its pore size distribution profile.
thicknesses being several hundred nanometers. Their hollow
plot (Fig. 1b), the experimental PXRD pattern is well
reproduced by the refined PXRD pattern.
To further confirm the as-prepared crystalline polymer
possessing the dual-pore COF structure as elucidated by PXRD
nature was strongly evidenced by the clear contrast between
the shells and the inner parts of the spheres (Fig. 4a, vide infra).
The as-prepared COF was firstly characterized by FTIR
spectroscopy. While nearly complete disappearance of the
analysis above, N adsorption-desorption measurements were
peaks corresponding to C=O and

NH indicates a high degree
2
2
carried out. The N adsorption curve of SIOC-COF-7 matched
of polymerization by consuming almost all the aldehydes and
amine groups of the monomers, a band assignable to the
2
the classical type I sorption model characterized by a steep
-1
nitrogen uptake in the low-pressure range (P/P = 0−0.01),
vibration of C=N was observed at 1619.8 cm , giving direct
evidence for the formation of imine linkages (Fig. S2, ESI). The
crystal structure of SIOC-COF-7 was elucidated by comparing
the experimental powder X-ray diffraction (PXRD) with the
simulated PXRD patterns which were generated by Accelrys
Materials Studio 7.0 software package. As illustrated in the
experimental PXRD profile (Fig. 1a), diffraction peaks at 2θ =
0
13
which is indicative of permanent microporosity (Fig. 2). Its
Brunauer-Emmett-Teller (BET) surface area was estimated
from the isotherm data in the range of P/P = 0.01−0.3, which
0
2
afforded a value of 618 m /g (Fig. S3, ESI). The total pore
volume was calculated to be 0.41 cm /g at P/P = 0.99. Its pore
3
0
size distribution was reflected by using non-local density
functional theory (NLDFT). It reveals that SIOC-COF-7 exhibits
two main pore size distributions at 5.0 and 11.8 Å, respectively
3
.24°, 5.94°, 10.03° and 23.16°, are observed, which are
assignable to the (100), (2-10), (1-20) and (001) facets,
respectively. In order to determine the packing manner of the
(Fig. 2b), which are almost same as the theoretical values of
5
.0 and 11.9 Å estimated by PM3 calculations. This result
2
D layers, two stacking models, eclipsed AA stacking (Fig. 1c)
corroborates again that SIOC-COF-7 possesses two different
kinds of micropores, with the one centered around 11.8 Å
being attributed to the deformed hexagonal pores and the
smaller one assignable to the parallelogram pores (Fig. S4, ESI).
After the structure of SIOC-COF-7 has been established, its
iodine capture capacity was then examined. The experiment
was carried out by exposing a certain amount of SIOC-COF-7 to
excess iodine vapor at 75 °C and ambient pressure, which is
close to the typical nuclear fuel reprocessing conditions. Upon
standing, the COF darkened gradually, indicating that iodine
diffused into the COF (Fig. 3a, inset). The performance for
iodine capture was investigated by gravimetric method (see
and staggered AB stacking (Fig. 1d), were constructed and
their theoretical PXRD patterns were simulated. It was found
that the simulated PXRD pattern of the AA stacking model
coincided with experimental PXRD data, strongly suggesting
that the as-prepared powder holds the dual-pore COF
structure as illustrated in Scheme 1 and the 2D layers adopt
eclipsed packing. The disappearance of (1-10) and (3-10) peaks
in the experimental PXRD pattern might be resulted from a
preferential orientation of the microcrystals. Pawley
refinement yielded unit cell parameters of a = 32.22 Å, b =
1
8.41 Å, c = 3.91 Å, α = β = 90°, and γ = 122.78°, with factors of
Rwp = 3.65% and Rp = 2.84%. As revealed by the difference
2
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a 500
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450
400
350
300
250
200
150
100
DOI: 10.1039/C7CC01045A
I2 vapor
5 oC
7
0
10
20
30
40
50
60
Time (h)
b
c
1400
C
d
1600
400
1200
000
Cu
N
1
1
200
000
I2
1
I
1
800
600
400
200
0
8
6
4
00
00
00
C
I
N
Cu
Cu
Cu
I
O
Cu
200
0
Cu
Fig. 3 (a) Gravimetric uptake of iodine as a function of time at 75 °C . (b) Cartoon
illustration for iodine capture in the spherical COF. Note: Some of iodine
molecules encapsulated in the shell were removed for clarity.
I
I
O
I
0
5
10
0
5
10
Energy (keV)
Energy (keV)
ESI for the procedure). On the basis of the data obtained, an
iodine loading curve of SIOC-COF-7 was plotted as a function
of time. As can be seen in Figure 3a, within the initial 15 hours
the amount of iodine uptake increases quickly and an uptake
of 391 wt % is observed after 15 hours. Along with the
extending of time, the rate of adsorption slows down and an
iodine uptake of 481 wt % (4.81 g iodine per 1.00 g SIOC-COF-7
is obtained after 48 hours. No obvious change in the iodine
loading amount is observed between 48 and 60 (486 wt %)
hours, implying that a saturated adsorption is achieved after
)
Fig. 4 TEM images of SIOC-COF-7 (a) before and (b) after the COF being exposed
4
8 hours. This value of iodine uptake is considerably higher to iodine vapor and EDX profiles of the COF (c) before and (d) after being
exposed to iodine vapour, and (e) EDX element mapping image of an iodine-
than those of all the previously reported solid porous loaded microsphere, and (f) TEM image of a sample fabricated by heating the
adsorbents including metal-based porous zeolitic materials, were generated from the copper support grids
iodine-loaded COF at 160 °C for 6 hours. Note: the copper peaks in EDX profiles
MOFs and amorphous POPs (see detailed comparisons in Table
S1), and the capturing rate of SIOC-COF-7 is comparable to capture by providing a large amount of storage space for
them, suggesting that SIOC-COF-7 is an excellent iodine iodine molecules. It is reasonable because the eclipsed
adsorbent. TGA analysis was also performed for the iodine- stacking of the layers of SIOC-COF-7 and its dual-pore feature
loaded COF under a nitrogen atmosphere. The TGA curve leads to the formation of two kinds of channels (dimeters ca. 5
revealed a significant weight loss of the iodine-loaded COF in and 12 Å, respectively) across the shells of the COF spheres,
the range of 90 to 350 °C. Since the pristine COF is stable which not only can accommodate iodine molecules but also
under this condition, the mass loss should be mainly attributed facilitate diffusion of iodine molecules into the inner cavities of
to the release of iodine from the iodine-loaded COF upon the microspheres due to the hierarchical porosity which can
being heated. The mass loss of iodine was thus estimated to be improve mass transport and decrease diffusion barriers (Fig.
4
93 wt % relative to the mass of SIOC-COF-7 (Fig. S5, ESI). The 3b). This assumption was proved by TEM investigations. As can
iodine uptake capacity derived from TGA analysis is fully in be seen in Figure 4a and 4b (also Fig. S6 in the ESI for
consistence with that obtained by gravimetric method above.
magnified TEM images), the hollow spheres exhibit clear
This record value promoted us to investigate why SIOC-COF- contrast between the shells and inner parts. However, the
7
has such high iodine uptake capacity. Since SIOC-COF-7 has a contrast completely disappears after exposing the COF to
3
total pore volume of 0.41 cm /g, a theoretical maximum iodine iodine vapor for 48 hours, which suggests that the inner
uptake of 202 wt % would be calculated from the product of cavities of the hollow microspheres are filled with iodine.
density of solid iodine and the total volume of the COF by
The spherical COF before and after being exposed to iodine
assuming all the pores were filled with iodine molecules. This vapor was also investigated by energy-dispersive X-ray (EDX)
value is still far lower than the experimental result 481 wt %, spectroscopy (Fig. 4c and 4d). For the pristine microspheres,
not to mention in the case of the pores just being partially strong peaks corresponding to carbon and nitrogen appear (a
filled. Therefore, there should be extra space accounting for weak peak corresponding to oxygen was also observed and it
the extraordinarily high iodine uptake of SIOC-COF-7. Since could be attributed to the residual C=O groups at the
SIOC- COF-7 exists as hollow microspheres, we envisioned that peripheral of the COF). In the case of iodine-loaded
the inner cavities of the COF microspheres as well as their microspheres, in addition to the peaks of carbon and nitrogen,
porous spherical shells should be responsible for the iodine
strong peaks corresponding to iodine are also observed. The
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iodine encapsulated in the microspheres was also visually
illustrated by EDX element mapping, from which uniform
dispersion of iodine in the whole microsphere could be
observed (Fig. 4e). The iodine encapsulated in the COF
microspheres can be released by heating the iodine-loaded
COF under vacuum. It is evidenced by the TEM image of a
sample fabricated by heating the iodine-loaded COF at 160 °C
for 6 hours at 0.01 MPa, for which clear contrast between the
shells and the inner parts was observed again (Fig. 4f). The
regenerated hollow COF spheres were further reused to
capture iodine by exposing it to iodine vapor again. It was
found that the iodine uptake still maintained at 96% of its
initial capacity after the COF was used five times (Fig. S7, ESI),
Notes and references
View Article Online
DOI: 10.1039/C7CC01045A
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,
solution of iodine (10.0 mmol L ) in a small sealed vial at
ambient temperature, the purple solution was found to fade
slowly and became colorless 9 hours later, accompanied with
the color of SIOC-COF-7 getting darker and darker (Fig. S8, ESI).
This result suggested that the iodine was encapsulated in the
COF. Its iodine capture capability in hexane was estimated to
be 127 wt % (Fig. S8, ESI). The lower iodine uptake in solution
than that of solid state could be attributed to the co-
encapsulation of solvent molecules. For the inner cavities of
the COF microspheres, in particular they should be filled with
iodine solution, instead of pure iodine, which significantly
decreases its iodine capture capacity. The captured iodine
could be readily released from the COF by immersing the
iodine-loaded material in ethanol at room temperature. The
color of the ethanol solution deepened from colorless to dark
brown as time went on, which clearly indicates that the iodine
guests were dissociating from the spherical COF (Fig. S10, ESI).
In summary, a novel heteropore 2D COF has been
synthesized. It exists as hollow microspheres and exhibits an
extremely high volatile iodine capture capacity. An iodine
uptake of 481 wt % has been obtained, which is the highest
value reported to date. While the abundant aromatic rings,
high nitrogen content and well-ordered network of the hetero
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Acknowledgements
We thank the National Natural Science Foundation of China 14 S. Kandambeth, V. Venkatesh, D. B. Shinde, S. Kumari, A.
Halder, S. Verma and R. Banerjee, Nat. Commun., 2015,
786.
6,
(No. 21472225, 21632004) and the Strategic Priority Research
6
Program of the Chinese Academy of Sciences (Grant No.
XDB20000000) for financial support.
4
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