Fabrication of conjugated microporous polytriazine nanotubes and nanospheres for highly selective CO2 capture

Article abstract of DOI:10.1039/c7cc00704c

A one-spot template approach for fabricating porous organic nanotubes was developed and a molecular design, i.e. introducing thiophene and s-triazine functionalities to enhance host-guest interactions, lead to novel porous solids with high capacities for CO₂ and exceptionally high ideal selectivities over N₂ for effective gas storage and separation.

Full text of DOI:10.1039/c7cc00704c

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Marilyn M. Olmstead, Alan L. Balch, Josep M. Poblet, Luis Echegoyenet al.
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Fabrication of Conjugated Microporous Polytriazine Nanotubes
and Nanospheres for Highly Selective CO2 capture
Zhiqiang Wang,‡a,b Junling Liu,‡b Yu Fu,b Cheng Liu,c Chunyue Pan,b Zhiyong Liu,a,∗ and Guipeng Yub,
Received 00th January 20xx,
Accepted 00th January 20xx
∗
DOI: 10.1039/x0xx00000x
www.rsc.org/
Abstract: A one-spot template approach for fabricating porous most frequent forms are aggregated microspheres15. Also, there are
organic nanotubes was developed and a molecular design, i.e. jagged
small amount of layered sheets16 core-shell17
a
,
,
introducing thiophene and s-triazine functionality to enhance morphologies18 and irregular shapes19. Tubular NOPs are very rare
host-guest interactions leaded to novel porous solids with high due to the lack of proper synthetic protocols and remain highly
capacities for CO2 and exceptionally high ideal selectivities over N2 desired not only for their fascinating tubular nanostructure which
for effective gas storage and separation.
provides access to three different contact regions (inner, outer
surfaces and ends) but also for good flexibility in functionalization
as well as sufficient understanding of the morphology-physical
property relationships. Deng et al. have reported nanotube-like
CMPs and their great potentials for separation of organic solvents
and oils from water20 and also demonstrated the significant impact
of reaction mediums on morphologies of as-made CMPs21. Son
disclosed the tubular-shape evolution of amorphous MONs
prepared by Sonogashira coupling between tetrahedral multialkyne
and dihalo building blocks.22 Notably, nanocarbons-templated
method has been developed for the construction of microporous
Covalently linked nanoporous organic polymers (NOPs) have
attracted increasing interests for their excellent physic chemical
properties and promising potential in gas storage1, separation2,
electronics3 and biosensors4. From the viewpoint of the material
synthesis, NOPs-due to their functional diversity-combine flexible
design and synthetic diversity, and are a growing platform for such
applications5,6. As for synthetic strategies, a kaleidoscope of organic
reactions namely condensation of aromatic diboronic acids7,
ionothermal reaction8, Suzuki cross-coupling reaction9, and
Yamamoto-type Ullmann coupling reaction10 have been successfully
employed. Purely organic nanoporous mainly micro-/meso-porous
materials as well as their construction technology are however still
a contemporary field of materials chemistry.
networks with well-defined nanotube morphologies23
. The
convenient, simple operation and easy-handling methods for the
production of morphology-controllable NOPs remains an aspect
that need to more contribution to insight into.
For an ideal sorbent materials with good absorption capability,
high pore volume, large specific surface area, and suitable
adsorption enthalpy and morphology11 are essential. To achieve this
goal, topological combination of the building units with different
geometries and sizes have been used to change the skeletons and
pores of the materials. Up to now, most research efforts have been
paid to improve the specific surface area12 and host-guest
It has been proven that introduction of electron-rich aromatic
rings and heteroatoms such as nitrogen24 can significantly improve
host-guest interaction of NOPs and their performance as a porous
medium for the storage of small gases. Thiophene, as an electron-
rich aromatic ring containing sulfur, is one of the most popular and
well-established building units acting as an electron donor in
organic conductive polymers while is rarely used for the
construction of NOPs. Herein, we attempted to develop an
undisclosed thiophene-based conjugated microporous polymer
(termed as CMP-CSU13) featuring good affinity towards CO2 and
significantly high selectivity of CO2 against nitrogen (Fig. 1). We also
demonstrate a facile in-situ template approach for fabricating
tubular meso-/micro-porous networks with controlled dimensions
under mild conditions.
interaction13 and to adjust pore size14
. While more recently
reducing the size of NOPs to nanometer scale has attracted
continuously increasing attention. As for the morphology of NOPs,
a.
College of Chemistry and Chemical Engineering, Key Laboratory for Chemical
Materials of Xinjiang Uygur Autonomous Region/Engineering Center for Chemical
Materials of Xinjiang Corps, Shihezi University, Xinjiang, Shihezi 832003, China. E-
mail: lzyongclin@sina.com.
In this regard, the thiphene moiety was successfully introduced
into the porous polymer backbone using a popular grown method
used to obtain Porous Aromatic Fameworks6. Starting from a
triangular monomer namely 2,4,6-tris(5-bromothiophen-2-yl)-1,3,5-
triazine (TBPT), the targeted CMP-CSU13 (Fig.1a) were readily obtai-
b.College of Chemistry and Chemical Engineering, Central South University,
Changsha 410083, China. E-mail: gilbertyu@csu.edu.cn.
c. State key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian
110762, China.
† These authors contributed equally to this work.
Electronic Supplementary Information (ESI) available: [Materials, Characterization
Methods and results, Synthesis procedures, etc.]. See DOI: 10.1039/x0xx00000x
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continuous search for synthetic conditions for purely tubular
materials, equivalent amount of 1,2-dibromoethane plus [Ni(cod)2]
against 2,2’-bipyridyl is a dominant factor for reliable generation of
tubular networks. Varying the molar content of 1,2-dibromoethane
and 2,2’-bipyridyl and their concentrations, the size of the
nanocrystals can be well controlled, leading to tubular porous
networks with tunable dimensions. For comparison, 0D ball-like
CMP (CMP-CSU13 sphere) was also prepared by the same
procedure without the addition of 1,2-dibromoethane.
The structure of TBPT (Scheme S1) was confirmed by spectral
measurements (Fig.S3-4, ESI†). The CMP-CSU13 obtained are
insoluble in all organic solvents and also chemically stable in dilute
solutions of acids and bases. Differentials canning calorimetry (Fig.
S5, ESI†) and thermo gravimetric analysis (Fig.S6, ESI†) demonstrate
their good thermal stability. The residual weight (around 1 % under
air atmosphere) at 800 oC, may be scripted to the presence of nickel
oxide and silicon oxide generated by oxidation of residual catalyst,
well agreeing with EDS mapping result (Fig. S7, ESI†).
Fig. 1 (a) Chemical structure and illustration, (b) FT-IR spectrum, (c) 13C/MAS NMR
spectrum, (d) PXRD patterns of CMP-CSU13 tube (Red) and sphere (Blue).
ned through Nickel (0)-catalyzed Yamamoto-type Ullmann coupling
which was known as an aryl-aryl coupling of aryl-halogenide
compounds mediated mostly by bis(1,5-cyclooctadiene)nickel(0)
with a proposed mechanism (Fig. S1, ESI†)25. Under such conditions,
our halogenide TBPT demonstrated an unexpected halogen
elimination ability, making the development of ultrahigh porosity
polymers easily accessible. Therefore, high-degree-crosslinking
networks with abundant thiophene units were successfully
obtained in decent yields (exceeding 71 %).
FT-IR (Fig. 1b) and 13C/MAS NMR spectra (Fig.1c) of tubular and
ball-like CMP-CSU13 matched well with the expected structure. The
tested element contents by Element Analysis show
a slight
deviaꢀon (Table. S1, ESI†), which may be reasonable considering
that trace amount of cocatalyst like 2,2’-bipyridyl trapped in the
pores even after an overnight Soxhlet extraction. PXRD patterns
indicate both the tubular and ball-like samples are amorphous (Fig.
1d). A careful comparison of the FT-IR, 13C/MAS NMR and PXRD
patterns suggests that there is no clear difference between the
tubular samples and spheres ones. These prove that the
incorporation of in-situ generated nanocrystal templates did not
affect the polymerization reaction significantly.
Our strategy for preparing porous nanotubes is rather simple, and
the idea was inspired by the nanocarbon-templated method23 and
also rod-shaped structure and the high surface-energy of
nanocrystals26
. Given the fact this Yamamoto-type Ullmann
In order to probe morphology texture of CMP-CSU13, scanning
electron microscopy (SEM) and TEM measurements were carried
out. It is clear from SEM images that the tubes are uniform noodle-
like fibers entangled with each other (Fig. 3a). Typically, the tubes
are several micrometers in length. Most of them have an outer
diameter of about 80–160 nm and a length of about 1-5 um,
depending on the molar content of 1,2-dibromoethane and 2,2’-
bipyridyl and also their concentrations in the reaction medium
(Table S2, Fig. S8-10, ESI†). Our results demonstrated an significant
increase on outer diameter of the nanotubes with the increasing
molar content of 1,2-dibromoethane and 2,2’-bipyridyl in the
polymerization system. Within a dilute polymerization system
(Entry 5), the majority of as-made nanotubes possess a decreased
diameter and length of 90±10 nm and 1-4um, respectively. Notably,
coupling polymerization was usually performed in dimethylformide
(DMF) with 2,2’-bipyridyl as an acid acceptor, it is proposed that the
nanocrystals, i.e. quaternary ammonium salts can be easily formed
in-situ by the quaterisation of 2,2’-bipyridyl with suitable
halogenide compounds (Fig. 2). In this way, the tubular polymers
may be accessed by using such nanocrystals as structurally directing
templates. While in such reaction conditions, we failed to directly
convert our aromatic halogenide compound (TBPT) to a quaternary
ammonium salt because of its low reactivity towards 2,2’-bipyridyl,
regardless of the potential great difficulty in further growing of
nanocrystals. 1,2-dibromoethane was chosen as a key additive in
our polymerization system to ensure the formation of ammonium
salts nanocrystals. At the polymerization temperatures, the charge
of 1,2-dibromoethane readily converted part of 2,2’-bipyridyl into
its water-soluble ammonium salt, which was precipitated out and
then the expected nanometer-sized rod-like crystals were formed
as confirmed by transmission electron microscopy (TEM, Fig. S2,
ESI†). Next, with the growing length of nanocrystals along their
axes, the crosslinking of polymers was carried out on the surfaces of
the nanocrystals, and thus, core/shell structures may be formed.
With the proceeding of the polymerization, oligomers like rigid
dendrimers or macrocycles were produced in the early stage, and
they were easily adhered onto the template surface due to the high
surface-energy of the nanocrystals. In the last purification step, the
nanocrystals inside the cavity of the products were easily removed
by washing with concentrated hydrochloric acid and water. In the
Fig. 2 Suggested mechanistic aspects of free-standing tubularCMP-CSU13
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the surfaces of the tubes are covered by spherical tubercles while there is no clear relationship with the nature of dispersion
featuring a diameter of about 10–30 nm, as shown in Fig.2a. The solvents (Fig. S11, ESI†). Permanent porosity of the CMP-CSU13 pair
TEM images (Fig. 2b and 2c) reveal that the resultant networks was confirmed by N2 adsorption/desorption isotherms (Fig. 4a). The
possess hollow tubular structures, further confirming the success of isotherms are Type I, albeit with a very modest micropore step and
in-situ template method. In contrast, without the addition of 1,2- some Type IV character. The BET surface area calculated was 741
dibromoethane in the polymerization system (Entry 0-1, Table S2, m2 g-1 for the tubular samples and this value is still comparable to
ESI†), only nanospheres accompanying with larger fused masses those reported for CMPs (200-900 m2 g-1) from similar aromatic
were observed (Fig. 2d). Further evidence comes from the TEM building blocks. Both CMP-CSU13 tubes and spheres show large
visualizations (Fig. 2e, 2f) in which the majority of the nanospheres total pore volumes up to 1.07 cc g-1, which is far larger than the
with a diameter of about 100–200 nm were demonstrated. Notably, famous CMPs with even higher surface areas3,24 (Tab. S3, ESI†). It is
in our investigated range the diameter of the porous shells could suggesting that the incorporation of thiophene into the backbone
easily be adjusted by varying the BFPT/solvent medium ratio (Table and the aryl-aryl coupling chemistry would effectively prevent the
S2, ESI†). Surface Gibbs free energy was probably the dominant collapse of the nanopores.
driving force to form CMP nanospheres in our system. Therefore, it
Unlike reported procedures23b
, our results indicate that
is reasonable considering the fact that the spherical structure has employing the nanocrystall templates in the preparation
the lowest surface Gibbs free energy compared with other procedures will not affect the pore structure of the as-made CMPs.
morphologies. High resolution TEM (HR-TEM) images exhibit Pore size distribution (PSD), as shown in Fig. 4b, was analyzed by a
alternating dark and bright areas, insinuating a porous structure of with Non-local density functional theory (NLDFT), and the pores in
the resulting networks. To exclude the possibility that the nanotube CMP-CSU13 are widely distributed, from micropore to mesopore, in
evolution in morphology was solely caused by the dispersion of the particular, mainly located in the range of 0.5 to 10 nm with
solvents or self-assembly after polymerization, four kinds of dominant pores centered at 0.6 and 1.4 nm, indicative of a
solvents with different polarity, i.e. n-hexane (Permittivity=1.9), hierarchal pore nature(Fig. S14-15, ESI†). Tubular sample possesses
ethanol (24.5), acetone (20.7) and water (78.5) were used to a wider pore size distribution with typical mesoporosity expanded
disperse the resulting samples. A careful comparison of HR-TEM to 8.2 nm, while these samples with different morphologies display
demonstrated that the nanotubes or aggregated microsphere some similarities in the PSD curves, implying their similar topology.
morphology just depends on the exact polymerization conditions,
CO2 sorption property was investigated by volumetric method at
273 and 298 K (Fig. 4c, Fig. S16, ESI†). A slightly higher CO2 uptake
capacity is attained by CMP-CSU13 nanosphere in comparison with
tubular one under same conditions, attributed to its larger pore
volume and easier diffusion of guest gases in the sphere
morphology. This implies that the morphology of the sorbents
exerts a significant effect for the low-pressure CO2 storage, and the
adsorption behaviour depends less on the surface area than that in
the high pressures. Compared to the reported CMPs, our CMP-
CSU13 exhibits the highest capacity although delivering a moderate
surface area. Such high capacities are also comparable to other
NOPs such as binaphthol-based HCPs (17.4 wt% at 1 bar and 273
K)11 and triazine-based CTF-0 (15.7 wt% at 1 bar and 273 K)8a.
The isosteric enthalpies of adsorption (Qst) were calculated by
Clausius-Clapeyron equation on the basis of the CO2 isotherms
recorded at 273 K and 298 K. The Qst values at a low coverage are
arranged in the following decreasing sequence (Fig. S17, ESI†):
CMP-CSU13 nanotube (40.3 kJ mol-1) > CMP-CSU13 nanosphere
(36.2 kJ mol-1). Both the samples deliver significantly high Qst values
(>35 kJ mol-1) for CO2 adsorption, surpassing those of other porous
organic polymers like CMP-1, PAF-1 (15.6 KJ/mol)27 and BILPs28. This
may be reasonable, considering the fact that the resultant networks
with abundant nitrogen or electro-rich thiophene units intrinsically
favour CO2 and contribute to the enhanced performance, because
of the promoted dipole-quadrupole interaction.
Fig. 3 SEM image (a), TEM image (b), HR-TEM image (c) of tubular CMP-CSU13;
SEM image (d), TEM image (e), HR-TEM image (f) of ball-like CMP-CSU13
The selective adsorption of CO2 over N2 is critical for carbon
capture from air or flue gas streams. Ideal selectivity of CO2 over N2
was calculated at an equilibrium partial pressure of 85 wt% N2 and
15 wt% CO2 in the bulk phase using IAST model29. The synthesized
CMP-CSU13 pairs deliver significantly high selectivities (Fig. 4d, Fig.
S18-21, ESI†). The tubular CMP-CSU13 possesses an unexceptionally
high ideal selectivity of CO2-over-N2 of 223 at zero coverage, being
Fig. 4 (a) N2 adsorption isotherms, (b) Pore size distributions by DFT method, (c)
CO2 adsorption isotherms, (d) IAST ideal selectivities of CMP-CSU13 tube (Red)
and sphere (Blue).
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This strategy was quite convenient in terms of handling and
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