A ribbon-like ultramicroporous conjugated polycarbazole network for gas storage and separation

Article abstract of DOI:10.1039/c5nj02567b

A new ultramicroporous conjugated network, P-TCzTAT, enriched with propeller-like carbazole building blocks was designed and synthesized by FeCl₃ oxidative coupling polymerization at room temperature. The adsorption isotherm of N₂ reveals that the polymer features a high Brunauer-Emmett-Teller (BET) specific surface area of 1028 m² g^-1 and a predominantly narrow pore width of 0.54 nm. The ultramicroporous polymer has strong affinity for CO₂, with high sorption abilities of 18.15% at 273 K and 1.1 bar and 10.69% at 273 K/1.1 bar and 298 K/1.1 bar, which can be ascribed to not only its optimal fraction of ultramicropores but also its high nitrogen content derived from the carbazole components. P-TCzTAT also exhibited potential application in gas storage and in CO₂/CH₄ and CO₂/N₂ gas separation.

Full text of DOI:10.1039/c5nj02567b

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Ribbon-like Ultramicroporous Conjugated Polycarbazole
Network for Gas Storage and Separation
Cite this: DOI: 10.1039/x0xx00000x
a,b
a
b
b
b
Shanlin Qiao‡ , Huan Wei‡ , Ting Wang , Wei Huang , Chunyang Gu, Renqiang
b
a
Yang * and Xiaoyun Li *
Received 00th January 2015,
Accepted 00th January 2015
A new ultramicroporous conjugated network P-TCzTAT enriched with propeller-like
configuration carbazole building block was designed and synthesized by FeCl3 oxidative
DOI: 10.1039/x0xx00000x
www.rsc.org/
coupling polymerization at room temperature. The adsorption isotherm of N
polymer features a high Brunauer-Emmett-Teller (BET) specific surface area of 1028 m g
reveals that the
2
2
-1
and predominant narrow pore width at 0.54 nm. The ultramicroporous polymer has strong
affinity for CO , with high sorption abilities of 18.15% and 10.69% at 273 K/1.1 bar and 298
2
K/1.1 bar, respectively, which can be ascribed to not only their optimal fraction of
ultramicropores but also the high nitrogen-contents derived from carbazole components. P-
TCzTAT also exhibited potential applications in gas storage and CO /CH4 and CO /N
2
2
2
separation.
Introduction
of most pore organic polymers (POPs) such as hyper-
2
3
In recent years, global warming has been emerging as an crosslinked polymers (HCPs),
international issue, which was attributed to the increasing microporosity (PIMs), and it is hard to get a pore with unique
emissions of greenhouse gas such as CO , CH and so on, distribution like inorganic porous materials. For example, most
polymers of intrinsic
2
4
2
4
because of the rapid consumption of hydrocarbon fuels. The CMP materials with superior surface areas exhibit broad pore
2
5,26
environmental agencies encourage the development of new width distribution from microporous to 10 nm,
suggesting
2
6
cost-effective technologies to cope the climate-changing the presence of both micropores and mesopores. Efficient gas
1
issues. In particular, CO capture and sequestration (CCS) in adsorption and separation of the CMPs depend on the high
2
physical process cooperating with clean energy source such as surface areas, narrow pore distribution and chemical
2
7
hydrogen, are of interest to meet the energy and environmental functionality. Both the initial building blocks and the
2
demands. To date, extensive efforts have been devoted to polymerization approaches show great influence on the above
developing CO capture and storage technologies and various three parameters. Among various starting materials, the unique
2
3
adsorbents were prepared and employed for this purpose.
structure of carbazole-containing block is a superior candidate
Among them, conjugated microporous polymers (CMPs) is a for polymerization as their potential active sites. It is well-
new series of porous materials with pore sizes comparable to known that the 3- and 6-positions of carbazole are oxidation
traditional porous solid sorbents, such as metal-organic sites to construct conjugated microporous materials through
4
,5
6-8
28,29
frameworks (MOFs), covalent organic frameworks (COFs),
FeCl oxidative coupling.
And it is worth pointing out that
They are besides the easy synthesis strategies, the carbazole-based CMPs
usually composed of light elements with large specific surface displayed remarkable CO2 capture and sequestration ability
3
9
,10
11,12
13-19
zeolites,
metal oxides
and porous carbons.
3
0,31
area and high chemical and thermal stability. The unique because of their high nitrogen-contents.
feature of CMPs is that they combine the stiff porous structure In this work, we report a ribbon-like conjugated polymer P-
and conjugated electron system in one bulk material. Those TCzTAT straightforward synthesized by FeCl3 oxidative
properties made CMPs to be an invaluable tool for less energy coupling polymerization at room temperature (Scheme 1). This
penalty and cost associated with state-of-the-art gas uptake facile polymerization approach, using single building block
2
0,21
application.
without any expensive catalysts and just requiring mild
Micropores are classified into ultramicropores (pore widths < conditions, is an economical and easier approach towards the
2
2
0
.7 nm) and supermicroporous (0.7 nm <pore widths<2 nm).
synthesis of conjugated pore networks in high yield. In
However, the wide pore size distribution is the typical property addition, both the flank part and the centre part of the starting
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block were consisted with carbazoles. The result will provide us showed P-TCzTAT has ribbon-like network which is different
3
4
insight about the effect of the propeller-type carbazole enriched from other reported porous organic polymers.
system on the gas adsorption ability. The obtained polymer P-
TCzTAT exhibits high surface area (1028 m g ), narrow
ultramicropore width (0.54 nm), and excellent gas storage and
separation capability.
(a)
(b)
2
-1
3
000
2000
1000
200
100
Chemical shift
0
-1
Wavenumbers (cm )
d
(ppm)
(c)
(
d)
(d)
0
20
40
60
Angle
(degree)
Scheme 1 Synthetic route of the carbazole-enriched network P-
TCzTAT.
13
Fig. 1 (a) FT-IR spectra, (b) C CP/MAS NMR spectra, (c) Powder X
ray diffraction and (d) Scanning electron microscopy image.
Results and discussion
The porosity properties of P-TCzTAT were measured by
adsorption analysis using nitrogen as the probe molecule at 77
K shown in Fig. 2a. The isotherms demonstrate steep rise in
The synthesis of the network P-TCzTAT is depicted in Scheme
1
.
Monomer TCzTAT with propeller-like geometrical
nitrogen uptake at the relative pressure (P/P ) less than 0.01,
0
configuration was prepared from carbazole by Ullmann
reaction catalyzed by cuprous. The rigid fused ring of carbazole
is beneficial for formation of polymers with permanent porosity
indicating significant microporosity in the obtained network.
The result was evidenced by the pore size distribution derived
from quenched solid density functional theory (QSDFT) in Fig.
stability, and the
N-containing structure can increase CO2-
2b. QSDFT is a multicomponent DFT, in which the network is
framework interactions by means of the dipole-quadrupole
treated as one of the components of the adsorbate-adsorbent
system and this model has been demonstrated that it can
significantly improve the accuracy of pore distribution
3
2
interactions. Inarching the short-chain ethyl groups on the
core will ensure the solubility of monomer to obtain a large
skeleton structure, and meanwhile, short and soft chains can
avoid the blocking of the micropores. TCzTAT, the core of
monomer, features a fused triazatruxene unit of asteroid
structure, which is a typical two-dimensional (2D) planar
35
compared to nonlinear density functional theory NL-DFT.
600
(a)
(b)
3
3
450
configuration. The polymerization of TCzTAT extends the
discotics core with three flanked carbazoles, which will change
the configuration of the polymer from 2D to 3D.
3
00
50
0
P-TCzTID
1
The structure of P-TCzTAT network was confirmed by FT-IR
spectra (Fig. 1a) and solid state magic angle spinning
P-TCzTID @ Ad
P-TCzTID @ De
1
3
C
CP/MAS NMR spectra with assignments of the resonances as
shown in Fig. 1b. The broad peaks in FTIR spectrum indicated
0.0
0.2
0.4
0.6
0.8
1.0
0
2
4
6
8
10
Relative pressure P/P
Pore width (nm)
0
-
1
-1
the high crosslinking of the polymer and 744 cm , 1224 cm ,
-
1
Fig. 2 (a) N2 adsorption-desorption isotherm of the carbazole based
network P-TCzTAT at 77 K, and (b) pore size distribution obtained by
the QSDFT method.
and 1469 cm are the characteristics vibration mode of
carbazole unit. The NMR spectra shows a signal at 14 ppm
which corresponds to the carbon atoms of the ethyl group.
Thermogravimetric analysis (TGA, Fig. S1) trace shows that
P-TCzTAT has the dominant ultramicropores width centered at
.54 nm which is beneficial for gas storage and separation.
When the Brunauer–Emmett–Teller (BET) model is adopted to
calculate the apparent surface area, the value of P-TCzTAT is
028 m g . Its total pore volume and micropore volume
the thermal decomposition temperature (T 5 wt%) is up to ca.
d
0
2
80 °C. Powder X ray diffraction (P-XRD, Fig. 1c) revealed P-
TCzTAT was amorphous aggregation without any crystalline
phase. Scanning electron microscopy image (SEM, Fig. 1d)
2
-1
1
3
-1
3
-1
calculated at P/P = 0.99 and 0.1 are 0.76 cm g and 0.4 cm g ,
0
2
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respectively. It is important to note the limitation of the N with surfaces. CO is an acidic adsorbate with a quadrupole moment,
2
2
a kinetic diameter of 3.64 Å, which is difficult to probe the which influences the adsorption behavior inside the
3
6
ultramicropore less than 5 Å, so we believe that the actual ultramicropores structure and on the alkaline surface. The
surface area of P-TCzTAT is higher than the value calculated performance of the carbazole-enriched polymer P-TCzTAT is
here. P-TCzTAT, featuring with high BET surface area, competitive to the reported MOPs under the similar condition,
4
1
39
ultramicropores and electron-rich system, will be a good such as BLP-1H of 7.4 wt%, COF-103 of 7.6 wt%, MCTFs
candidate for gas sorption and storage.
4
2
43
of 13.9 wt%, CMP-1 of 9.02 wt%, etc.
Physisorption of methane in principle can provide a safe and
economical approach for energy densities storage comparable
2
1
1
0
0
.0
.5
.0
.5
.0
to compressed gas at much lower pressures. The CH uptake for
4
P-TCzTAT was measured up to 1.1 bar (Fig 4a). The CH4
uptake of P-TCzTAT is 2.09 wt% at 273 K/1.1 bar and 1.19
wt% at 298 K/1.1bar, respectively. It is noteworthy that the
P-TCzTAT
-
1
isosteric heat of P-TCzTAT can be up to 38.55 KJ mol at zero
-1
loading and keep almost stable at 22 KJ mol on the whole
0
.0
0.4
0.8
1.2
Absolute pressure (bar)
loading range (Fig 4b), which is higher than the Qst of non-
4
4
conjugated pore networks. The high isosteric heat allows the
possibility of greater storage capacities at lower pressures for
materials with appropriate microporous size and volume.
Fig. 3
2
H adsorption isotherm of network P-TCzTAT at 77 K.
Hydrogen physisorption by porous materials is an immensely
important topic in the clean energy application. The H sorption
isotherm of P-TCzTAT was measured at 77 K (Fig. 3), which
2
0
.4
0.10
0.08
CO2
CO2
CH4
y CO2 = 5.28065X + 0.03534
CH4
0.3
y CO2 = 14.40162X + 0.19983
2
2
shows a 1.92 wt% H uptake at 77 K and 1.1 bar. This value is
N2
R
= 0.99746
N2
2
R
= 0.99731
0
.06
0.04
.02
0.00
attractive compared to most of pore materials under the similar
y CH4 = 0.85319X + 0.02707
0.2
2
3
7
y CH4 = 2.08678X + 0.01645
2
R
= 0.98707
condition, for example, polyaniline is 0.85 wt%, CMP-2 is
R
= 0.99913
3
8
39
40
y N2 = 0.19466X + 0.00194
0
.91 wt%, COF-103 is 1.25 wt%, PPN-3 is 1.58 wt%. The
0.1
y N2 = 0.49234X + 0.00241
2
R = 0.99994
2
0
R
= 0.99964
adsorption curve shows that no saturation is achieved,
(b)
(
a)
0.0
indicating that a larger H capacity can be obtained at higher
2
0.00
0.05
0.10
0.15
0.20
0.25
0.00
0.05
0.10
0.15
0.20
pressure condition.
Absolute pressure / bar
Absolute pressure / bar
Fig. 5 Initial gas uptake slopes of the network at (a) 273 K and (b) 298 K.
25
20
15
10
5
0
40
Ad-273K @ CO2
De-273K @ CO2
Ad-298K @ CO2
De-298K @ CO2
Ad-273K @ CH4
To further investigate the separation ability of polycarbazole P-
TCzTAT, the gas selectivity of the polymer for CO /CH and
30
20
10
0
2
4
Ad-298K @ CH4
CO /N2 were estimated using the ratios of the Henry law
2
constants calculated from the initial slopes of the pure
CO2
CH4
45
(a)
(b)
component isotherms at low pressure range, as shown in Fig.
5
. The calculated CO /CH selectivity of P-TCzTAT at 273
2 4
0.0
0.2
0.4
0.6
0.8
1.0
0.0
0.5
1.0
1.5
2.0
2.5
K/1.1 bar and 298 K/1.1 bar is 6.9 and 6.4, respectively. The
selectivity of CO /N at 273 K/1.1 bar and 298 K/1.1 bar is 29.3
Absolute pressure (bar)
Amount adsorbed (mmol/g)
2
2
and 27.1, respectively. One can observe that P-TCzTAT show
stabile CO /CH and CO /N selectivity even if the temperature
rises from 273 K to 298 K. It could be concluded that the
ultramicropores (pore width < 0.7 nm) is advantageous for gas
separation.
Fig. 4 (a) Adsorption isotherms of CO
2
and CH
4
, (b) variations of
2
4
2
2
isosteric enthalpies with the adsorbed amount of CO
2
and CH
4
.
The CO and CH adsorption isotherms were collected at 273
2
4
K/0~1.1 bar and 298 K/0~1.1 bar, respectively, as shown in Fig
a. CO physisorption process is reversible as the desorption
4
2
Conclusions
branches are very close to those of adsorptions. The CO uptake
2
capacity of P-TCzTAT can be up to 18.15 wt% and 10.69 wt% In summary, a new carbazole-enriched polymer was designed
at 273 K/1.1 bar and 298 K/1.1 bar, respectively. The isosteric and synthesized with a facile method. The polymer features
enthalpy (Qst) of P-TCzTAT for CO uptake is calculated to be unique ultramicroporous structure. Extending the planar core of
2
-
1
3
3.42 KJ mol at zero loading based on Clausius-Clapeyron triazatruxene with three carbazoles increases the torsion angle
equation shown in Fig. 4b. It can also retain the heats of and forms a propeller-like building block. The obtained
-
1
adsorption at 29 KJ mol as the increasing adsorption network P-TCzTAT exhibits narrow pore distribution with the
quantities, which indicated a superior CO2 capture capacity domain pore centerd at 0.54 nm. Gas (H , CO and CH4)
2
2
despite the relatively modest surface area. The high CO uptake adsorption isotherms show that the H storage can reach 1.92
2
2
may be ascribed to the ultramicropores and nitrogen-rich wt % (1.1 bar and 77 K) and uptake capacity for CO and CH
2
4
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Acknowledgements
This work was supported by the National Natural Science
Foundation of China (21274161, 51173199, 51303197 and
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(
2010DFA52310).
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Institute of Chemical Industry and Pharmaceutical Engineering, Hebei
University of Science and Technology, Shijiazhuang 050000, China
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b
CAS Key Laboratory of Bio-based Materials, Qingdao Institute of Bioenergy
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‡
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J. Name., 2015, 00, 1-3 | 5

New Journal of Chemistry
Page 6 of 6
View Article Online
DOI: 10.1039/C5NJ02567B
Graphical abstract
Ribbon-like ultramicroporous conjugated polycarbazole network P-TCzTAT have high BET
surface area and narrow pore width distribution was synthesized.