Constructing POSS and viologen-linked porous cationic frameworks induced by the Zincke reaction for efficient CO2 capture and conversion

Article abstract of DOI:10.1039/c8cc06972g

POSS and viologen-linked porous cationic frameworks (V-PCIF-X, X = Cl, Br) are constructed via the Zincke reaction between octa(aminophenyl)silsesquioxane and viologen linkers. The typical V-PCIF-Br has a high surface area with abundant ionic sites, micro

Full text of DOI:10.1039/c8cc06972g

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Constructing POSS and viologen-linked porous cationic
frameworks induced by Zincke reaction for efficient CO2 capture
and conversion
Received 00th January 20xx,
Accepted 00th January 20xx
Guojian Chen,*a Xiaohui Huang,a Yadong Zhang,a Mengyao Sun,a Jie Shen,a Rui Huang,a Minman
Tong,a Zhouyang Long*a and Xiaochen Wangb
DOI: 10.1039/x0xx00000x
www.rsc.org/
POSS and viologen-linked porous cationic frameworks (V-PCIF-X, Crafts reaction19,20 and polymerization21 have been adopted to
X=Cl, Br) are constructed by Zincke reaction between fabricate POSS-based porous polymers. However, their neutral
octa(aminophenyl)silsesquioxane and viologen linkers. The typical skeletons exclude them from the diverse applications where the
V-PCIF-Br possesses a high surface area with abundant ionic sites, charged ionic sites are indispensable. To our knowledge, only
micro-/mesopores and Si-OH groups, serving as an efficient several low-surface-area POSS-derived solvable oligomers or ionic
porous adsorbent and metal-free catalyst for simultaneous CO2 copolymers combined with catalytic active heteropolyanions were
capture and conversion.
prepared for heterogeneous catalysis.22,23 Recently, we have
developed a series of porous cationic frameworks (PCIFs) with high
surface areas via one-pot quaternization of ClMePOSS with N-
heterocyclic linkers.24 However, these PCIFs own low ionic densities,
which hampers their ion-exchange capacities or further catalytic
performance. Hence, the present work focuses on constructing
POSS-based PCIFs that have both high ionic densities and desired
surface areas via a new strategy.
Porous ionic polymers (PIPs)1,2, as a new class of porous polymers,
have rapidly emerged in various forms of ionic covalent organic
frameworks (iCOFs),3-6 ionic covalent triazine frameworks (iCTFs),7,8
ionic porous organic polymers (iPOPs)9-11 and mesoporous
poly(ionic liquid)s (MPILs).12-14 Compared with the neutral skeletons
of organic frameworks, PIPs possess featured charged cationic or
anionic skeletons paired with counter-ions. As a versatile ionic solid
platform, guest functional groups and ionic species can be facilely
introduced by ion-exchange, which endows PIPs with enhanced
abilities towards gas storage, separation and conversion, catalysis,
water treatment, electrolytes and electrodes in Li-ion battery,
etc.1,2 Currently, the synthetic strategies towards PIPs mainly
depend on the methods of their parent COFs or POPs by replacing
neutral linkers with ionic linkers. The related reactions include
Schiff-base condensation,4-6 trimerization,7 coupling reaction9-11 and
free-radical polymerization,12-14 generally with the assistance of
expensive/toxic catalysts or additives. Obviously, it is highly
desirable to develop new tactics to directly construct porous ionic
frameworks under catalyst-free condition, wherein the key point is
to design new building units and seek suitable synthetic methods.
Polyhedral oligomeric silsesquioxanes (POSS) are a category of
well-defined inorganic silica nanocages surrounded by organic
functional groups,15 which have been regarded as ideal building
blocks for constructing porous inorganic-organic hybrid polymers.
To date, different reactions related to C-C coupling,16-18 Friedel-
Herein, we report a facile catalyst-/template-free strategy for
fabricating POSS and viologen-linked porous cationic frameworks
(denoted as V-PCIF-X, X=Cl, Br) paired with halogen anions induced
NH2
R
H2N
O
O
Si
Si
O
Si
R
O2N
O
O
O
Si
O
R
X
O
Si
O
O
O
O2N
N
N
X
NO2
+
O
R
Si
NH2
NO2
NH2-POSS
R=phenylamine
VL-X (X=Cl, Br)
H2N
Zincke reaction
DMF, 180 oC, 48 h
O
X
N
X
N
R
X
X
N
POSS
N
CO2 (0.1 MPa)
O
O
Si
O
O
Si
Si
OH
O
O
O
=
Viologen linker
O
O
O
Si
O
O
O
O
Si
R
O
O
X
N
High yields
X
N
O
POSS
X
N
Si-O-Si linker
X
N
V-PCIF-X (X=Cl, Br)
Scheme 1 The synthetic route to construct POSS and viologen-linked porous cationic
frameworks induced by Zincke reaction towards catalytic conversion of CO2.
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by Zincke reaction of octa(aminophenyl)silsesquioxane (NH2-POSS)
with two specially designed viologen-based dual Zincke salts (VL-X,
X=Cl, Br), as depicted in Scheme 1. Very recently, Zincke reaction
has been used for preparing conjugated covalent organic networks
(CONs) with diverse morphologies, but only offering low surface
areas (12~153 m2 g-1).25,26 In this contribution, micro-/mesoporous
V-PCIF-X with large surface areas can be fabricated by Zincke
reaction under solvothermal conditions. Distinguishingly, 3D rigid
NH2-POSS molecules tethered with eight phenylamine groups
provide multiple positions or directions around one POSS cage for
interlinking viologen moieties, which affords organic-inorganic
hybrid porous cationic frameworks. The typical sample V-PCIF-Br
possesses a large surface area up to 383 m2 g-1, a high ionic density
and POSS-derived Si-OH groups, behaving as a remarkable porous
adsorbent for CO2 capture and metal-free heterogeneous catalyst
for CO2 cycloaddition with epoxides under mild conditions.
Fig. 1 (A) 29Si MAS NMR spectrum of the typical sample V-PCIF-Br. (B) FTIR spectra of
VL-Br, NH2-POSS and V-PCIF-Br. (C) N2 adsorption-desorption isotherms and (D) NLDFT
pore size distributions of V-PCIF-X (X=Cl, Br).
The typical synthesis of V-PCIF-X is accomplished by the
solvothermal Zincke reaction between NH2-POSS and viologen
linkers VL-X in DMF at 180 oC for 48 h in Teflon-lined autoclaves
without stirring (see ESI for details). It is worth noting that the new
POSS), due to the partial distortion and condensation of POSS cages
with coexistence of Tn and Qn units, while V-PCIF-Cl gives similar
structure (FTIR, Fig. S6, ESI). In a word, the detailed formation
process (Scheme S3, ESI) is initially induced by Zincke reaction and
then involves successive reaction-triggered cleavage of Si-C bonds
and further condensation of Si-OH groups, which works together to
construct the Tn and Qn combined POSS and viologen-linked V-PCIF-
Br. Just right, the in-situ formed T2 and Q3 units within V-PCIF-Br
afford abundant Si-OH for boosting catalysis represented latter.
The full XPS survey spectra for V-PCIF-X (Fig. S7A) exhibit all
elements of C, N, O, Si and Br (Cl) in the targeted porous cationic
frameworks. The N1s core-level spectra (Fig. S7B) can be fitted to
three peaks at 405.4, 400.1 and 398.7 eV attributed to the N-oxide
(NO2), N atoms of the bipyridinium and NH2 groups, respectively.8,11
Elemental analysis shows the high N contents for V-PCIF-X (Table
S1), and most of these N atoms are N+ cations, plus small amounts
of residual NO2 and NH2 groups identified by N1s XPS. Further, the
ionic site contents of V-PCIF-Br and V-PCIF-Cl are 5.72 mmol g-1 and
6.56 mmol g-1 determined by testing the halogen anions amounts
with ion chromatography.11 Energy dispersive X-ray absorption
spectroscopy (EDS) mapping images describe the uniform
distribution of C, O, N, Br (Cl) elements in V-PCIF-X (Figs. S8-S9),
again confirming high N+ ionic sites paired with halogen anions.
The porosities of V-PCIF-X (X=Cl, Br) are evaluated in terms of
N2 sorption isotherms at 77 K. As shown in Fig. 1C, V-PCIF-Cl and V-
PCIF-Br exhibit type IV isotherms with considerable uptakes at low
relative pressure (P/P0 <0.1) and distinct H1 type hysteresis loops at
P/P0 in the range of 0.5-0.95, indicating the presence of micropores
and mesopores. The pore size distributions calculated by the NLDFT
model (Fig. 1D) displays that V-PCIF-Br owns micropores centered
at 1.48 nm and abundant mesopores distributed around 9.31 nm,
confirming its micro-mesoporous structure, while V-PCIF-Cl exhibits
two dominant mesoporous peaks at 3.95 and 7.18 nm. Mesoporous
distributions centered at 13.11 nm for V-PCIF-Br and 3.94 nm for V-
PCIF-Cl are also determined by the BJH method (Fig. S10). V-PCIF-Cl
and V-PCIF-Br possess large BET surface areas (SBET) of 174 and 383
m2 g-1 with the total pore volumes of 0.28 and 0.70 cm3 g-1 (Table
S1), respectively. V-PCIF-Br paired with larger Br− anions possesses
1
crystalline Zincke salt VL-Br (Scheme S1, Fig. S2 for HNMR and 13C
NMR and Fig. S3 for XRD) is firstly synthesized and applied to
fabricate porous cationic polymers, while VL-Cl has been used for
preparing viologen monomers27 or CONs.25,26 This synthetic process
(see Scheme S2 for the detailed mechanisms) involves nucleophilic
attack by multiple primary amine of NH2-POSS onto dual Zincke salt
VL-Br with the subsequent electrocyclic ring opening and ring
closing followed by elimination of 2,4-dinitroaniline,25 directly
producing POSS and viologen-linked porous cationic frameworks.
The successful preparation of V-PCIF-Br is confirmed by the
solid-state 13C and 29Si NMR spectra, Fourier-transform infrared
(FTIR) spectra. The solid-state 13C CP/MAS NMR spectrum (Fig. S4)
of the typical material V-PCIF-Br shows broad multi-peaks at
δ=122.6~150.2 ppm centered at 129.7 ppm attributable to the
carbon signals in phenyl and bipyridium moieties within the formed
cationic networks. 29Si MAS NMR spectrum (Fig. 1A) reveals the
coexistence of T2 and T3 units [Tn: CSi(OSi)n(OH)3-n], Q3 and Q4
moieties [Qm: Si(OSi)m(OH)4-m] in V-PCIF-Br.24 The chemical shift at
δ=-79.1 ppm assigned to T3 unit confirms the retention of cubic
POSS cage structures originated from NH2-POSS molecule; A minor
T2 unit shown at δ=-72.6 ppm arises from partial Si-O cleavage of
POSS cages, which was also observed in other POSS-based porous
polymers.18-20 Q3 units (δ=-102.6 ppm) are formed due to the Si-C
bonds cleavage of T3 units, caused by the cross-linking of rigid
viologen linkers and release of basic 2,4-dinitroaniline; Q4 units
shown at δ=-108.6 ppm should be resulted from self-condensation
of Si-OH in the formed Q3 units.24 The existence of Si-OH groups in
V-PCIF-X is confirmed by the Si-OH vibration appeared at 3656 cm−1
from in-situ FTIR spectra (Fig. S5) under vacuum condition to
exclude the interference of the adsorbed water.28 In FTIR (Fig. 1B),
the decline of the characteristic -NH2 at 3358 cm-1 and -NO2 at 1344
and 1543 cm-1 and appearance of characteristic pyridinium υ(C=N)
peak at 1632 cm-1 and POSS υ(Si-O-Si) peak at 1129 cm-1 indicate
that the loss of 2,4-dinitroaniline and formation of POSS-cored
viologen-linked cationic polymers.24,25 The obtained V-PCIF-Br still
maintains Si-O-Si structure with the feature bands divided into
three peaks 1178, 1129 and 1108 cm-1 (1119 cm-1 for cubic NH2-
2 | J. Name., 2012, 00, 1-3
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Table 1 Cycloaddition of CO2 with epichlorohydrin catalyzed by V-PCIF-X under
different conditions.[a]
O
CO2 (T, P, t)
O
O
O
Cl
Cl
V-PCIF-X
T
(oC)
P
t
Yield
(%)[b]
Selectivity
(%)[b]
Entry
Catalyst
(MPa)
(h)
1
2
3
4
5
6
7
8
100
80
1
1
6
98
94
>99
>99
>99
>99
>99
>99
>99
>99
Fig. 2 (A) SEM image and (B) TEM image of V-PCIF-Br.
12
48
V-PCIF-Br
100
80
0.1
0.1
1
99
much higher BET surface area than that of V-PCIF-Cl with smaller Cl−
anions, which also surpasses all the SBET values (12~153 m2 g-1) of
CONs prepared by Zincke reaction.8,25,26 The key synthetic
parameters including molar ratios of NH2-POSS and VL-Br, solvents,
temperatures are systematically investigated and the textural
properties of V-PCIF-Br series are significantly affected (Figs. S11-
S13 and Tables S2-S4). It is worthy to note that the high-boilling
solvent DMF is more suitable for affording high-surface-area V-PCIF-
Br at 180 oC. We suggest that the boiling DMF can rapidly take away
the reaction-released 2,4-dinitroaniline (molecular dimension ca.
0.94 nm, the optimized structure see Fig. S14) from the resulted
frameworks, which together plays a molecular template role for
creating intrinsic micropores in V-PCIF-Br.
48/72
6
86/97
94
100
100
80
V-PCIF-Cl
VL-Br [c]
0.1
1
48
80
12
90
80
0.1
48
84
[a] Reaction conditions: epichlorohydrin (5 mmol), CO2 pressure (P=1 MPa or 0.1
MPa), catalyst V-PCIF-X (0.05 g, 2.9 mol% based on VL), temperature (T=80 120
oC), time (t=6 72 h); [b] Yield and selectivity of the cyclic carbonate determined
by GC and 1HNMR. [c] The amount of VL-Br (0.01 g).
~
~
many other PIPs with halogen anions.7,10,11,13,29 With the increase of
CO2 uptake, the Qst values present sharp decline and tend to be
stable around 30 kJ mol-1 at high CO2 loadings, which is important
for the regeneration and recycle for CO2 capture. A five run cycling
CO2 adsorption isotherms of V-PCIF-Br are observed for no loss of
CO2 capacity (Fig. S19C), suggesting its good regeneration stability.
The chemical fixation of CO2 with epoxides is one of the
promising routes to achieve the utilization of CO2 as a C1 building
block for preparing value-added cyclic carbonates. Although several
iPOPs and MPILs have been used as heterogeneous catalysts for
CO2 cycloaddition, to the best of our knowledge, this is the first
report of a highly efficient heterogeneous catalyst based on POSS-
based PCIFs within intrinsic halogen anions for CO2 conversion
under mild conditions. First, V-PCIF-Cl and V-PCIF-Br are employed
as heterogeneous catalysts in the typical CO2 cycloaddition with
epichlorohydrin in the absence of any solvent, co-catalyst (Table 1).
Under moderate CO2 pressure (1 MPa) at 100 oC for 6 h, the catalyst
V-PCIF-Br provides a very high yield of 98% with a perfect selectivity
(>99%), higher than that of V-PCIF-Cl (94%), attributing to the
higher nucleophilicity and better leaving ability of Br− than Cl−.14 To
our delight, V-PCIF-Br also affords a high yield of 99% under
Thermogravimetric analysis (TGA) shows that V-PCIF-Cl and V-
PCIF-Br have excellent thermal stability up to 400 oC with slight
weight losses both under N2 and air atmosphere (Fig. S15). X-ray
diffraction (XRD) patterns (Fig. S16) indicate the amorphous nature
of V-PCIF-X materials. Scanning electron microscopy (SEM) images
describe that V-PCIF-Br behaves a spongy morphology (Fig. S17)
assembled by the interconnected nanoparticles with the sizes
ranging from 20 to 30 nm (Fig. 2A). The observable mesopores (ca.
10 nm) are originated from nanovoids among packed nanoparticles,
well consistent with the pore size distribution centered at 9.31 nm.
In contrast, V-PCIF-Cl with smaller mesopores ranging from 3.95 nm
to 7.18 nm behaves a more closely compacted morphology (Fig.
S18). Transmission electron microscopy (TEM) image (Figs. 2B)
further confirms that V-PCIF-Br has abundant mesoporous cavities
derived from the interconnected nanoparticles.
Owing to their nature of high surface areas and N-enriched
ionic sites, the CO2 adsorption performances of V-PCIF-X are further
investigated. CO2 adsorption isotherms of V-PCIF-X are measured up
to 1.0 bar at 273 K and 298 K (Fig. S19A). The sample V-PCIF-Br
exhibits the higher CO2 adsorption capacity of 2.33 and 1.66 mmol
g-1 at 273 K and 298 K than those of V-PCIF-Cl (1.97 and 1.41 mmol
g-1), due to its high surface area superior to V-PCIF-Cl. Remarkably,
the CO2 uptake capacity of V-PCIF-Br is much higher than those of
neutral POSS-based porous polymers in spite of their higher surface
areas,18,20 and comparable to those of porous ionic polymers with
large surface areas7,10,11,29,30, but still inferior to those over zeolites,
metal-organic frameworks (MOFs) and carbon adsorbents (the
details seen in Table S5). The high initial isosteric heat (Qst) values of
CO2 adsorption (Fig. S19B) are found to be 56.6 kJ mol-1 for V-PCIF-
Cl and 60.4 kJ mol-1 for V-PCIF-Br at low coverage, reflecting the
strong interaction between ionic moieties and CO2 molecules.7,10,13
The promoted CO2 adsorption and enthalpies indicate the positive
effect of cationic frameworks paired with Br− anions in enhancing
the CO2-philicity of V-PCIF-Br, which has been also revealed by
o
atmospheric CO2 (0.1 MPa) at 100 C for 48 h, while V-PCIF-Cl gives
a moderate yield of 80%. The catalyst V-PCIF-Br still achieves the
desired yields (94% at 1 MPa for 12 h, 86% for 48 h or 97% for 72 h
under 0.1 MPa CO2) at a lower temperature 80 oC (Table 1, entries 2
and 4). The heterogeneous catalyst V-PCIF-Br exhibits high yields
both under 1 and 0.1 MPa CO2 at 80 oC, even comparable to the
homogeneous viologen linker VL-Br (Table 1, entries 2, 4, 7 and 8).
A detailed comparison (Table S6) reveals that V-PCIF-Br is among
the most efficient ionic sites-containing metal-free hetergeneous
catalysts (such as iPOPs, MPILs) for this reaction,7,10,11,13,14,30 and
superior to several metal-containing iPOPs.31-33 Though some metal-
based POPs and MOF catalysts were reported as efficient catalysts
under milder conditions, they still relied on using metals and adding
a homogeneous co-catalyst TBAB (Table S7). A five run recycling test
shows that V-PCIF-Br exhibits good reusability without loss of
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5
6
N. Huang, P. Wang, M. A. Addicoat, T. Heine and D. Jiang,
Angew. Chem. Int. Ed., 2017, 56, 4982.
Z. Li, H. Li, X. Guan, J. Tang, Y. Yusran, Z. Li, M. Xue, Q. Fang, Y.
activities (Fig. S20), owing to the well preserved composition,
porosity and morphology of the recovered catalyst (Figs. S21-S23).
Besides, diverse epoxides including epibromohydrin, styrene oxide,
glycidyl phenyl ether, allyl glycidyl ether and 2-butyloxirane can be
efficiently converted into the cyclic carbonates with high yields of
90~99% under both 1 and 0.1 MPa CO2 pressure (Table S8). These
results demonstrate well substrate compatibility of V-PCIF-Br.
Evidently, V-PCIF-Br performs as a metal-solvent-additive-free
remarkable heterogeneous catalyst for cycloaddition of CO2. The
high activity of V-PCIF-Br can be attributed to its intrinsic
characteristics of high ionic density (i.e. nucleophilic Br− anions),
abundant mesoporosity and POSS-derived Si-OH groups. In detail,
the proposed catalytic process for the formation cyclic carbonates
using V-PCIF-Br is described in Scheme S4: (i) the activation of
epoxide is enhanced by H-bonding interaction between its O and H
atoms originated from POSS-derived Si-OH groups, which is a key
step as pointed out by previous reports;14,34,35 (ii) the activated
substrate 1 is subsequently attacked by nucleophilic Br− anions to
form an oxy-ion intermediate 2;7 (iii) the active intermediate then
reacts with inserted CO2 molecules to produce the corresponding
cyclic carbonate released from the catalyst V-PCIF-Br. This synthetic
route makes the high dispersion and homogeneous distribution of
Br− anions and Si-OH groups around POSS cores in V-PCIFs, which
accelerates the activation and conversion of epoxides and CO2.
These enriched ionic sites within high-surface-area porous cationic
polymers also improve the performance in CO2 capture and
enhance the concentration of CO2 inside the catalyst, thus
dramatically promoting catalytic activities under mild conditions.
In summary, a new synthetic strategy is reported to achieve
POSS and viologen-linked porous cationic frameworks induced by
Zincke reaction under solvothermal conditions. The obtained V-
PCIF-Br possesses a high surface area with versatile features of
micro-/mesoporosity, abundant ionic sites and enriched Si-OH
groups, which together contributes to the simultaneous CO2
capture and catalytic conversion of CO2 into value-added products.
Based on this Zincke reaction’s synthetic strategy, more ionic
porous organic frameworks are on the way, towards diverse
applications in catalysis, adsorption, energy storage and conversion.
We are grateful for financial support from National Natural
Science Foundation of China (Nos. 21603089, 21503098 and
21606066), Jiangsu Province Science Foundation for Youths
(BK20160209), NSF of the Higher Education Institutions of Jiangsu
Province (16KJB150014), NSITP (201710320041), TAPP and PAPD.
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