A Robust Metal-Metalloporphyrin Framework Based upon a Secondary Building Unit of Infinite Nickel Oxide Chain

Article abstract of DOI:10.1021/acs.cgd.5b01548

Herein we report the construction of a robust metal-metalloporphyrin framework that is based upon a rare secondary building unit of infinite nickel oxide chain. The constructed MMPF-20 exhibits permanent porosity and selective adsorption of CO₂ over CH₄ as well as demonstrates interesting catalytic performances in the context of olefin epoxidation.

Full text of DOI:10.1021/acs.cgd.5b01548

Article
pubs.acs.org/crystal
A Robust Metal-Metalloporphyrin Framework Based upon a
Secondary Building Unit of Infinite Nickel Oxide Chain
Weijie Zhang,†,‡ Wenyang Gao,‡ Tony Pham,‡ Pingping Jiang,*,† and Shengqian Ma*,‡
†The Key Laboratory of Food Colloids and Biotechnology, School of Chemical and Material Engineering, Jiangnan University, Wuxi
214122, P.R. China
‡Department of Chemistry, University of South Florida, 4202 East Flower Avenue, Tampa, Florida 33620, United States
S
* Supporting Information
ABSTRACT: Herein we report the construction of a robust
metal-metalloporphyrin framework that is based upon a rare
secondary building unit of infinite nickel oxide chain. The
constructed MMPF-20 exhibits permanent porosity and
selective adsorption of CO2 over CH4 as well as demonstrates
interesting catalytic performances in the context of olefin
epoxidation.
INTRODUCTION
RESULTS AND DISCUSSION
■
■
As a subclass of metal organic frameworks (MOFs),1,2 metal-
metalloporphyrin frameworks (MMPFs)3−11 have been attract-
ing an escalating interest due to their potential applications for
gas adsorption/separation,12−19 catalysis,20−33 light-harvest-
ing,34−39 etc. Despite their premature stage, some challenge
in the development of MMPFs as functional materials for the
aforementioned applications has been recognized to be the
preservation of structural integrity and permanent porosity after
removal of the guest solvent molecules.40−43 The combined use
of custom-designed multitopic porphyrin ligand and a robust
secondary building unit (SBU) represents an effective approach
to stabilize the MMPF structure and preserve its permanent
porosity. The employment of discrete multinuclear trivalent
(e.g., Al3+, Fe3+)44−46 or quadrivalent (e.g., Ti4+, Zr4+ and
Hf4+)47−54 metal clusters as SBUs has afforded a series of
robust and permanently porous MMPFs. Nonetheless, most
MMPFs based on divalent metal ions are very fragile upon
removal of guest solvent molecules.
It has been reported that MOFs with infinite metal oxide
chains as SBUs can usually preserve their permanent porosities
upon the removal of guest solvent molecules as well exemplified
in the MOF-74 series.55,56 It can be envisioned that the
robustness of divalent metal ion-based MMPFs will be boosted
if such kinds of infinite metal oxide chain SBUs can be
incorporated into their framework structures. In this con-
tribution, we report the first MMPF based upon a SBU of
infinite nickel oxide chain as illustrated in the construction of
MMPF-20 which exhibits permanent porosity and selective
adsorption of CO2 over CH4 as well as interesting catalytic
performances in the context of olefin epoxidation.
Crystals of MMPF-20 were formed via solvothermal reactions
of the 5,10,15,20-tetrakis (4-carboxyphenyl) porphyrin
(H2TCPP) ligand and NiCl2·6H2O in dimethylforamide
(DMF) at 150 °C. The product was isolated as rod-shaped
purple crystals (Figure S1) of Ni3(Ni-TCPP)2·1.4DMF·9H2O
at 46% yield. The overall formula was determined by X-ray
crystallography, elemental analysis, and thermogravimetric
analysis (TGA).
Single-crystal X-ray analysis reveals that MMPF-20 crystal-
lizes in the space group C2/c and the asymmetric unit consists of
two Ni(II) ions and one Ni-TCPP ligands, which are metalated
in situ (Figure 1a). Ni1 is six-coordinated by six oxygen atoms
with a distorted octahedral geometry, of which two are from
two bidentate bridging μ2-η1η1 carboxylate groups and four are
from two tridentate bridging μ2-η2η1 carboxylate groups; Ni2 is
four-coordinated by four oxygen atoms from four different
carboxylate groups with a tetrahedral geometry (Figure 1b).
The binuclear Ni motifs are interconnected through the
carboxylate bridges to form a rare infinite one-dimensional
(1D) nanosized ribbon chain as an SBU. Alternatively, each
TCPP ligand coordinates with eight Ni atoms of four
neighboring Ni chains to propagate into an overall three-
dimensional (3D) framework structure with 1D channels of
∼4.6 Å × 12.6 Å (van der Waals radii included) along the a axis
(Figure 1c,d). The solvent accessible volume of MMPF-20
calculated using PLATON is 38.0%.57
The phase purity of MMPF-20 sample was verified by
powder X-ray diffraction studies, which indicate that the
diffraction patterns of the as-synthesized sample are consistent
Received: October 31, 2015
Revised: December 26, 2015
© XXXX American Chemical Society
A
DOI: 10.1021/acs.cgd.5b01548
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To examine the permanent porosity of MMPF-20, gas
adsorption studies were performed on the activated sample. As
shown in Figure 2a, the N2 adsorption isotherm collected at 77
K indicated that MMPF-20 exhibited an uptake capacity of 259
cm3g−1 at the saturation pressure with typical type-I sorption
behavior, as expected for microporous materials. Derived from
the N2 data, MMPF-20 has a Brunauer−Emmett−Teller (BET)
surface area of 517 m2g−1 (P/P0 = 0.05−0.3), which is
confirmed by CO2 adsorption isotherm at 195 K (Figure S5).
Meanwhile, MMPF-20 can also preserve its crystallinity and
framework integrity after activation as evidenced by powder X-
ray diffraction (PXRD) studies (Figure S2).
We investigated the performances of MMPF-20 in selective
adsorption of CO2 over CH4. Under 1 atm pressure, MMPF-20
can adsorb 43 cm3 g−1 at 273 K, whereas its CH4 uptake
capacity is 12 cm3g−1 at 273 K under the same pressure (Figure
2b). To predict the adsorption selectivity of CO2 over CH4, the
ideal adsorption solution theory (IAST),60 which has been
validated for calculating the adsorption selectivity of gas
mixtures in MOFs,61 was employed by applying single-
component adsorption isotherms. From selectivity plots of
CO2/CH4 (50/50) shown in Figure 3, MMPF-20 is calculated
to exhibit an adsorption selectivity of 8 for CO2 over CH4 at
273 K and 1 bar, which is comparable to that of other
porphyrin-based MOFs.26,28,30
Figure 1. (a) The asymmetric unit and coplanar conformation in
MMPF-20. (b) Infinite ribbon chain-shaped metal-carboxylate
building unit in MMPF-20, (c) structural features of MMPF-20
along the a direction, and (d) the structure of MMPF-20 viewed along
the b direction. Color scheme: Ni, turquoise; C dark gray; O, red; N,
blue; H atoms are omitted for clarity.
with the calculated ones (Figure S2). Thermogravimetric
analysis (TGA) studies of the fresh MMPF-20 sample (Figure
S3) reveal a weight loss of 12.5% from 25 to 150 °C
corresponding to the loss of guest water molecules and DMF
molecules trapped in the channels. X-ray photoelectron
spectroscopy (XPS) analysis shows a nickel signal at binding
energies at 855.4 and 873.0 eV corresponding to peaks of Ni
2p3/2 and Ni 2p1/2 respectively (Figure S4). A very weak
satellite peak at 863.1 eV is also observed in the XPS spectra,
indicating the predominant diamagnetic nature for Ni(II) ions
present in MMPF-20.58,59
Figure 3. Gas mixture adsorption selectivity are predicted by IAST at
273 K and 100 kPa for MMPF-20.
Figure 2. (a) N2 adsorption isotherms of MMPF-20 at 77 K, (b) CO2 and CH4 adsorption at 273 K.
B
DOI: 10.1021/acs.cgd.5b01548
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Table 1. Epoxidation of Conjugated Olefins with Different Electron-Donating and Withdrawing Groups Catalyzed by MMPF-
a
20
a
Substrate (0.2 mmol), TBHP (0.4 mmol), catalyst (0.002 mmol), acetonitrile (10 mL), and bromobenzene 100 mg as internal standard sealed in a
b
Teflon-lined screwcap vial were stirred at 80 °C. After three cycles.
It has been well documented that metalloporphyrins are
capable of catalyzing the epoxidation of alkenes.62 Considering
the rare studies on the electronic effect on transforming
conjugated olefins into epoxides, we decided to evaluate the
performances of MMPF-20 as heterogeneous catalyst in the
context of epoxidation of conjugated olefins with different
electron-donating and withdrawing groups on double bond or
phenyl ring. Catalytic assays for the epoxidation of iso-
propenylbenzene were first carried out. As shown in Table 1,
MMPF-20 exhibits good catalytic activity in terms of both yield
(66%) and selectivity (85%). It is obvious that the methyl
group connected to the double bond of styrene can effectively
enhance the yield of epoxide, as compared to the substrate
styrene (Table 1, entry 2). In contrast, withdrawing groups on
the phenyl rings or double bond can reduce the epoxide yield.
For instance, a decrease in epoxide yield is observed when the
substrate changes to 4-chlorostyrene (Table 1, entry 3);
moreover, virtually no product was detected even after 24 h
when 2-bromoethenylbenzene with bromine substituent group
on double bond was employed as the substrate (Table 1, entry
4). On the other hand, extending the conjugation of substrate
molecules can afford higher the epoxide yields (Table 1, entry 5
and 6) given the electron donating effect of phenyl ring. It is
worth mentioning the slightly lower yield observed for trans-
stilbene compared with 2-vinylnaphthalene should be presum-
ably due to the steric hindrance. From the above results, it can
be hypothesized that the effect of donating groups around
double bond can enhance the epoxide yield to a certain extent,
and the positon of the donating groups also plays a crucial role
in the overall yield and selectivity. To further verify this
hypothesis, we strategically select another two substrates with
electron-donating group adjacent to the double bond, such as
4-methoxystyrene and 1-methoxy-4-[(1E)-1-propenyl] benzene
(Table 1, entry 7 and 8). As expected, the epoxidation turns out
to be very effective, with up to distinctly higher yield
particularly for the substrate 1-methoxy-4-[(1E)-1-propenyl]
benzene. This can be tentatively interpreted that a higher
electron density on double bond usually increases the
nucleophilicity of conjugated olefins toward electrophilic
oxygenating intermediates.63
No detectable leaching of active site was observed in the
reaction solution for the oxidation of isopropenylbenzene after
removal of MMPF-20 by filtration, confirming the heteroge-
neous nature of the catalyst. Moreover MMPF-20 can retain its
structural integrity (Figure S3) and can be reused for three
cycles without significant drop in its catalytic activity (Table 1,
entry 1). A BET analysis after catalysis showing a slight
reducetion in Figure S6 demonstrates the robustness of
MMPF-20.
CONCLUSION
■
In summary, we have demonstrated the employment of infinite
metal-oxide chain-based SBU for the construction of a robust
metal-metalloporphyrin framework as exemplified by MMPF-
20 that is based upon the SBU of infinite nickel oxide chain.
The robustness of MMPF-20 has been assessed by gas
adsorption and PXRD studies, which show that MMPF-20
possesses permanent porosity and retains crystallinity/frame-
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ASSOCIATED CONTENT
■
S
* Supporting Information
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.cgd.5b01548.
CCDC reference number 1005654 for MMPF-20.
Experimental procedures for powder X-ray diffraction
patterns, TGA plots, crystal data of MMPF-20 (PDF)
(21) Farha, O. K.; Shultz, A. M.; Sarjeant, A. A.; Nguyen, S. T.;
Accession Codes
Hupp, J. T. J. Am. Chem. Soc. 2011, 133, 5652.
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CCDC 1005654 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_
request@ccdc.cam.ac.uk, or by contacting The Cambridge
Crystallographic Data Centre, 12, Union Road, Cambridge
CB2 1EZ, UK; fax: +44 1223 336033.
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AUTHOR INFORMATION
■
Corresponding Authors
*E-mail: ppjiang@jiangnan.edu.cn.
*E-mail: sqma@usf.edu; Tel: +1-813-974-5217.
Notes
(28) Xie, M. H.; Yang, X. L.; He, Y.; Zhang, J.; Chen, B.; Wu, C. D.
Chem. - Eur. J. 2013, 19, 14316.
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS
■
W.Z. thanks the foundation of the China Scholarship Council
(CSC). This work was supported financially by the National
“Twelfth Five-Year” Plan for Science & Technology
(2012BAD32B03) and the Innovation Foundation in Jiangsu
Province of China (BY2013015-10). The authors also acknowl-
edge NSF (DMR-1352065) and USF for partial support of this
work.
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