Knitting Aryl Network Polymers-Incorporated Ag Nanoparticles: A Mild

Oct 10, 2017 - A simple and scalable method for synthesizing silver nanoparticles supported on the framework of mesoporous knitting aryl network polym...
2 downloads 0 Views 3MB Size
Download PDF
Letter Cite This: ACS Sustainable Chem. Eng. 2017, 5, 9634-9639

pubs.acs.org/journal/ascecg

Knitting Aryl Network Polymers-Incorporated Ag Nanoparticles: A Mild and Efficient Catalyst for the Fixation of CO2 as Carboxylic Acid Zhilian Wu,†,‡,∥ Qinggang Liu,‡ Xiaofeng Yang,*,‡ Xue Ye,‡ Hongmin Duan,‡ Jian Zhang,‡ Bo Zhao,§ and Yanqiang Huang*,‡

Downloaded via NAGOYA UNIV on June 26, 2018 at 19:26:53 (UTC). See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.

†

CAS Key Laboratory of Renewable Energy, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, No. 2 Nengyuan Road, Wushan Street, Guangzhou 510640, China ‡ State Key Laboratory of Catalysis, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Dalian Institute of Chemical Physics, Chinese Academy of Sciences, No. 457 Zhongshan Road, Dalian 116023, China § State Key Laboratory of Advanced Power Transmission Technology (Global Energy Interconnection Research Institute), Changping District, Beijing 102211, China ∥ University of Chinese Academy of Sciences, No.19 (A) Yuquan Road, Shijingshan District, Beijing 100049, China S Supporting Information *

ABSTRACT: A simple and scalable method for synthesizing silver nanoparticles supported on the framework of mesoporous knitting aryl network polymers (KAPs) has been developed. With the benefits from its mesoporous texture and the stabilizing effect of phosphine compounds in the matrix, the silver precursor can be efficiently introduced into the KAPs framework, which results in a nanosize distribution of Ag (ca. 4.1 nm) supported on KAPs (Ag/ KAPs-P) with narrow particle size distribution and homogeneous dispersion after simple reduction step. The as-obtained metal smallsized Ag/KAPs-P catalyst is particularly active for the direct carboxylation of terminal alkynes with CO2 into carboxylic acid at low temperature and atmospheric pressure. Moreover, this Ag/KAPs-P catalyst also shows high stability under the reaction conditions, and it can be recycled at least five times without significant loss of activity, suggesting its great potential application in the heterogeneous conversion of CO2 into carboxylic acid. KEYWORDS: Carbon dioxide, Porous organic polymers, Heterogeneous catalyst, Alkynyl carboxylic acid

■

INTRODUCTION The excessive emission of CO2 due to the increased usage of fossil fuels has become an urgent issue as it causes a series of environment problems.1−4 While on the other hand, in terms of its nontoxicity, renewability, and accessibility, CO2 is also considered as a “green” carbon source,5−7 and thus, the conversion of CO2 into chemicals has attracted ever-increasing interests.8−11 Among them, the formation of C−C bonding products is one of the most promising avenues12,13 in which carboxylic acid is the most facile product owing to its similarity in form to the parent CO2. More importantly, carboxylic acid can serve as not only key structural motifs in medical chemistry, but also as versatile building blocks for the construction of bioactive molecules and conductive polymers.14−17 Recently, several homogeneous catalytic processes have been reported; however, further application was severely hampered by either the recycling problems or the high ligand sensitivity to water or air.18−20 Thereafter, a few heterogeneous metal catalysts for this reaction have also been reported, but the performance of supported catalysts is still underdeveloped due to their poor yield of desired product, harsh reaction conditions, or difficult catalyst preparation.21−25 More recently, we have successfully © 2017 American Chemical Society

prepared a Schiff-base-modified silver catalyst on the silica support, which shows excellent activity.26 Even so, the sizes of silver nanoparticles are not well dispersed due to the easy aggregation of silver nanoparticle in the preparation process, which limits its catalytic performance in the carboxylation of alkynes. Therefore, the development of a more efficient and robust heterogeneous Ag nanocatalyst featuring simple, green, and scalable preparation is still in great demand, yet remains challenging. Porous organic polymers (POPs) have recently created new opportunities for the development of heterogeneous catalysis.27,28 Particularly, Tan and his colleagues have reported a low-cost strategy to synthesize high surface area knitting aryl network polymers (KAPs) by using a simple one-step Friedel− Crafts reaction.29−31 KAPs have several interesting advantages, such as a simple synthesis method and different kinds of monomers that give diverse functional polymers.29,32 Accordingly, it can be imagined that with KAPs as a support for silver Received: August 4, 2017 Revised: September 24, 2017 Published: October 10, 2017 9634

DOI: 10.1021/acssuschemeng.7b02678 ACS Sustainable Chem. Eng. 2017, 5, 9634−9639

Letter

ACS Sustainable Chemistry & Engineering

(FTIR) spectroscopy, high resolution scanning electron microscope-energy dispersive spectroscopy (HRSEM-EDS), elementary analysis (EA), and inductively coupled plasma atomic emission spectroscopy (ICP-AES). FTIR spectroscopy of KAPs-P and KAPs-Py (Figure S1) display a series of bands around 1630−1615, 1250−950, and 900−650 cm−1, which can be attributed to benzene or pyrrole skeleton stretching and C− H out-of-plane bending and in-plane bending vibrations of the benzene ring, respectively, while the peaks at 1439 and 1448 cm−1 belonged to the vibrations of the P−CH2 bond and C− N−C skeleton, respectively.31 The morphology of the KAPs was investigated by HRSEM-EDS (Figure 1). It formation of

nanoparticles it can be more beneficial to distribute metal nanoparticles on the support by the mesopores and/or functional-group modification,33 which then would offer great opportunity for performance promotion in this direct carboxylation reaction. Herein, we report a simple route to prepare a series of novel Ag/KAPs catalysts by NaBH4 reduction of silver precursors under room temperature. Moreover, by modification of KAPs with phosphine, the Ag/ KAPs-P catalyst can be homogeneously dispersed on the support with small size distribution and act as an excellent catalyst with good recyclability in the conversion of CO2 to alkynyl carboxylic acids under mild reaction conditions.

■

RESULTS AND DISCUSSION KAPs with or without the modification of triphenylphosphine (PPh3) in the matrix (Scheme S1) were used as supports to anchor Ag NPs to form Ag/KAPs-P and Ag/KAPs-Py catalysts by the reduction of silver tricyanomethanide (AgTCM) precursor or by using AgNO3 as a precursor to prepare the Ag*/KAPs-Py sample, as shown in Scheme 1 (see the Supporting Information (SI) for experimental details). All three catalysts have the same Ag loadings of 0.1 wt %, which were detected by inductively coupled plasma atomic emission spectroscopy (ICP-AES). The successful growth of the network with PPh3 and pyrrole functional groups was confirmed by Fourier transform infrared

Figure 1. SEM images of (a) KAPs-P and (b) KAPs-Py.

solid spheres with submicrometer dimensions for KAPs-P and aggregated nanoparticles for KAPs-Py were revealed. The element maps (EDS) for KAPs-P (Figure S2) confirmed that N and P were homogeneously distributed throughout the KAPs-P matrix. Further analysis of the networks by element analysis (EA) and ICP-AES indicates KAPs-P was mainly composed of C (58.29 wt %), H (3.68 wt %), N (4.77 wt %), and P (1.58 wt %), while KAPs-Py contained C (54.86 wt %), H (3.79 wt %), and N (11.04 wt %). The CO2 sorption properties of samples KAPs-P and KAPsPy were then investigated at room temperature and atmosphere pressure (Figure 2). The uptakes of CO2 were 17.2 and 24.3

Scheme 1. Synthetic Route of (a) Ag/KAPs-P, (b) Ag/KAPsPy, and (c) Ag*/KAPs-Pya

Figure 2. CO2 adsorption/desorption (298 K) of KAPs-P and KAPsPy.

cm3/g for KAPs-P and KAPs-Py, respectively. These values are comparable with those well-known POPs materials under identical conditions,34,35 indicative of the good sorption capacity of KAPs toward CO2, which might be beneficial for the following conversion of CO2. The porous properties of KAPs-P, KAPs, and corresponding catalysts were measured by N2 sorption analysis. Significant decreases in the amount of N2 sorption and the sizes of pore diameters were observed for both

a

Magenta balls represent PPh3 functional groups; green balls represent Ag NPs. Solid line represents boundary of material particles. Dashed lines represent inner network of material particles. 9635

DOI: 10.1021/acssuschemeng.7b02678 ACS Sustainable Chem. Eng. 2017, 5, 9634−9639

Letter

ACS Sustainable Chemistry & Engineering Ag-loaded samples in comparison with the corresponding supports. The decrease in SBET and pore volume should be attributed to the incorporation of the Ag NPs into the pores of KAPs and/or a block of Ag NPs located on the framework surface of KAPs (Figure S3, Table S1). Ag NPs immobilized in KAPs-P and KAPs-Py was characterized by powder X-ray diffraction (PXRD) patterns, X-ray photoelectron spectroscopy (XPS), and transmission electron microscopy (TEM). The PXRD patterns in Figure S4 show that no silver peaks were observed for all the as-prepared Ag catalysts (Ag/KAPs-P, Ag/KAPs-Py, and Ag*/KAPs-Py) due to the low loading of silver on the support. X-ray photoelectron spectroscopy (XPS) result (Figure 3) of Ag/

Figure 4. HR-TEM images of (a) Ag/KAPs-P, (b) Ag/KAPs-Py, (c) Ag*/KAPs-Py, and (d) recycled Ag/KAPs-P catalysts. Insets are the corresponding metal size distributions.

Table 1. Synthesis of 3-Phenylpropiolic Acid from CO2 and 1-Ethynylbenzenea Figure 3. XPS spectra (Ag-3d levels) of fresh and recycled Ag/KAPs-P catalyst.

KAPs-P indicated that the silver ions were successfully reduced to Ag (0) nanoparticles by the NaBH4. To further study the Ag/KAPs catalysts, the morphology of the silver NPs deposited on the support of KAPs was characterized by high resolution transmission electron microscopy (HRTEM). The HRTEM images (Figure 4) confirmed that the silver NPs in Ag/KAPs-P were homogeneously dispersed with a smaller size (4.1 ± 1.4 nm) than that in Ag/KAPs-Py (9.8 ± 5.4 nm) and Ag*/KAPsPy (17.5 ± 9.6 nm). This can be explained by the promotion effect of phosphine in the dispersion and stabilization of Ag components.33,36−49 For one thing, the p-electron pair of P leads it as an efficient ligand for the Ag precursor, which can promote ligand exchanges with the AgTCM and help to disperse Ag precursors into the mesoporous of KAPs. For another, it is also beneficial to the anchoring of Ag nanoparticles, which hampers its aggregation during the reduction process. As a result, a small-sized Ag nanoparticle can be facilely obtained over KAPs-P materials. The comparative catalytic activities of the Ag/KAPs catalysts were evaluated for the conversion of CO2 with terminal alkynes into propiolic acids. In our initial investigation, the carboxylation of 1-ethynylbenzene was selected as a model reaction to investigate the influence of various parameters on the reaction. It has found that, under the conditions of 60 °C, 1.0 atm of CO2, and 6 h, the reaction in DMSO gave only 37% yield in the absence of catalyst, and the only presence of KAPs-P shows no contributions on the yield of product (entries 1−2, Table 1). In contrast, when the Ag/KAPs-P catalyst was added as a catalyst, the yield was greatly promoted to 74% (entry 3, Table 1). As a reference catalyst, however, Ag/KAPs-Py gave a relatively poor yield (66%, entry 4, Table 1), which was likely due to its larger

Entry

Catalyst

Base

Solvent

T

Yield

1 2b 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17c

None KAPs Ag/KAPs-P Ag/KAPs-Py Ag*/KAPs-Py Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P Ag/KAPs-P

Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3 Na2CO3 K2CO3 KTB Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3 Cs2CO3

DMSO DMSO DMSO DMSO DMSO DMSO DMSO DMSO Dioxane MeCN PC DMF DMSO DMSO DMSO DMSO DMSO

60 60 60 60 60 60 60 60 60 60 60 60 40 50 70 80 60

37% 37% 74% 66% 59% trace 2% 20% trace 2% 3% 5% 29% 55% 83% 89% 92%

a

Reaction conditions: 1-ethynylbenzene (1.0 mmol), catalyst (10 mg), base (1.5 mmol), CO2 (1.0 atm), solvent (5 mL), 6 h. bWith KAPs-P or KAPs-Py as a catalyst. cReaction time was extended to 10 h.

metal sizes (9.8 ± 5.4 nm) compared with that of the Ag/ KAPs-P catalyst. Correspondingly, the Ag*/KAPs-Py catalyst resulted in the lowest yield (59%, entry 5, Table 1) owing to its largest metal particle size in these three samples. Cs2CO3 is one of the most commonly used bases in various organic reactions.50 Here, Cs2CO3 was also considered as the superior choice for this carboxylation reaction of 1ethynylbenzene with CO2, which is consistent with the results in previous reports.18,21,26 Among those other bases we screened, Na2CO3, K2CO3, and potassium tertbutoxide (KTB) resulted in rather poor yields (entries 6−8, Table 1). Moreover, the impact of the polar organic solvents was proved 9636

DOI: 10.1021/acssuschemeng.7b02678 ACS Sustainable Chem. Eng. 2017, 5, 9634−9639

Letter

ACS Sustainable Chemistry & Engineering Table 2. Substrate Scope Tests over the 1c Catalysta

to be the other key factor influencing this reaction, and dimethyl sulfoxide (DMSO) was the best one. That is, under the conditions of 60 °C and 1.0 atm of CO2, 74% yield was obtained in DMSO over the Ag/KAPs-P catalyst (entry 3, Table 1), while only a trace, 2%, 3%, and 5% yields were obtained in the solvents of 1,4-dioxane (dioxane), acetonitrile (MeCN), propylene carbonate (PC), and N, N-dimethylformamide (DMF), respectively (entries 9−12, Table 1). Therefore, both the base and solvent are important factors in determining the high yield of CO2 to carboxylic acid, and the combination of Cs2CO3 with DMSO plays an important role on the high yield toward carboxylic acid. It was deduced that the stronger polar solvent (DMSO) may promote the dissolution of Cs2CO3 in the liquid phase, which was responsible for alkynes to free the terminal protons by forming the Ag−C intermediates for further carboxylation. A similar solvent effect of DMSO in the carboxylation of terminal alkynes was also found in our other reported studies.19,26,51 According to our previous results, the same mechanism for the carboxylation of terminal alkynes was proposed over this Ag/ KAPs-P catalyst; that is, the terminal alkyne was first coordinated to the small-sized silver NPs on KAPs-P and was then deprotonated by the Cs2CO3 in liquid phase to generate a silver acetylide intermediate, which was finally inserted with the carbon dioxide into its C−Ag bond to form the carboxylate. The synergistic effect between silver NPs and Cs2CO3 can thus extremely enhance the catalytic activity of this nanocatalyst system,21,25,26 and the small-sized Ag nanoparticles might promote the generation of silver acetylide intermediate on the catalyst. The influence of temperature on this carboxylation reaction was also studied, and it was proved that the catalytic performance of Ag/KAPs-P increased with the increase in temperature (entries 3 and 13−16, Table 1). Giving overall consideration to the temperature and activity, 60 °C was selected as an optimal temperature. Meanwhile, when reaction time was extended to 10 h, a higher yield (92%) can be obtained (entry 17, Table 1), and the Ag/KAPs-P catalyst has a large turnover number (TON, based on Ag content) of 9936, which to the best of our knowledge is the best one ever reported for the catalytic conversion of CO2 into alkynyl carboxylic acid (Table S2). In order to investigate the general application of such an Ag/ KAPs-P catalyst in the carboxylation reaction, the scope with respect to various other terminal alkyne substrates was then explored (Table 2). Under optimal conditions, with Ag/KAPsP (0.01 mol % of Ag), 1.5 equiv of Cs2CO3, 5 mL DMSO, 60 °C, and 1.0 atm CO2, the corresponding carboxylation products were achieved in promising yields (85−98%) regardless of aromatic alkynes with either the stronger electron-donating substituent (Table 2, entry 2) or with electron-withdrawing groups (entries 3−4, Table 2). A heterocyclic 3-ethynylthiophene was also tested, and a yield of 87% was achieved (entry 5, Table 2). Both the alkyl- and alkenyl-substituted terminal alkynes are also suitable for this procedure, thus giving the target alkynyl carboxylic acids in synthetically satisfactory yields of 89% and 85%, respectively (entries 6−7, Table 2). As a result, the Ag/KAPs-P catalyst can be widely and efficiently used for CO2 fixation by terminal alkynes as carboxylic acids. Finally, the reusability of the Ag/KAPs-P catalyst was investigated by using the carboxylation of 1-ethynylbenzene to the corresponding 3-phenylpropiolic acid as an example. For each run, the reaction was carried out under 1 atm pressure at

a

Reaction conditions: alkyne (1.0 mmol), Ag/KAPs-P (10 mg), Cs2CO3 (1.5 mmol), CO2 (1.0 atm), 60 °C, DMSO (5 mL), 10 h. b Isolated yields.

40 or 60 °C reaction temperature for 10 h (Figure 5). The catalyst after each run was filtered and washed with H2O and

Figure 5. Recycling tests of Ag/KAPs-P catalyst for the carboxylation of terminal alkynes with CO2. Reaction conditions: 1-ethynylbenzene (1.0 mmol), catalyst (10 mg), Cs2CO3 (1.5 mmol), CO2 (1.0 atm), DMSO (5 mL), 10 h, 60 °C (blue), or 40 °C (gray).

ethanol, followed by drying to remove the residues from the surface of Ag/KAPs-P. The catalytic activity of Ag/KAPs-P can retain its high yield toward 3-phenylpropiolic acid more than five times in the two series of experiments, and only a slight decrease in activity at 60 °C was observed with the yields ranging from 84% to 92%. It can be attributed to the durability of Ag NPs in the KAPs-P support during the reaction, which can hinder the great aggregation of Ag NPs in the reaction. Indeed, as suggested by the HRTEM image of the Ag/KAPs-P catalyst after five runs (Figure 4), the particle size of Ag NPs was only slightly aggregated, with a particle size of 6.0 ± 2.2 9637

DOI: 10.1021/acssuschemeng.7b02678 ACS Sustainable Chem. Eng. 2017, 5, 9634−9639

Letter

ACS Sustainable Chemistry & Engineering

also appreciate valuable discussions with Mr. Jiawei Zhong and Dr. Yancheng Hu.

nm, confirming the good stability of Ag/KAPs-P during the reaction process. Meanwhile, the XPS spectra of the recycled Ag/KAPs-P catalyst (Figure 3) indicated that the peak of 3d5/2 was shifted from 368.3 to 367.8 eV, which may be due to the partial oxidation of Ag NPs in the solvent of DMSO during the reaction.

■

■

CONCLUSION In conclusion, we have developed a new kind of KAP material with phosphine in its framework for supporting Ag nanoparticles. Because of the P anchoring sites in the matrix, silver nanoparticles can be introduced homogeneously into the mesoporous KAPs-P framework with the AgTCM as a precursor. Due to its small size of metal active sites, the asprepared Ag/KAPs-P catalyst exhibits efficient activity toward the direct carboxylation of terminal alkynes with CO2 to produce valuable carboxylic acids under a stronger polar solvent (DMSO), in which the dissolution of Cs2CO3 promotes to free the terminal protons of alkynes and form the Ag−C intermediate. Moreover, the stabilizing effect of phosphine also contributes to the antiaggregation of silver nanoparticles under the reaction conditions, and the Ag/KAPs-P catalyst can be recycled five times without significant loss of activity. Such an Ag/KAPs-P catalyst is of great potential application in the heterogeneous conversion of CO2 into carboxylic acid, and the synthesis route can also be extended to other metal NPs catalysts supported on KAPs-P.

■

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.7b02678. Experimental details, materials, methods, and characterizations, and Tables S1 and S2, Figures S1−S4, and Scheme S1). (PDF)

■

REFERENCES

(1) Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kuehn, F. E. Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? Angew. Chem., Int. Ed. 2011, 50, 8510−8537. (2) Su, X.; Xu, J. H.; Liang, B. L.; Duan, H. M.; Hou, B. L.; Huang, Y. Q. Catalytic carbon dioxide hydrogenation to methane: A review of recent studies. J. Energy Chem. 2016, 25, 553−565. (3) Li, B.; Xu, Z. X.; Jing, F. L.; Luo, S. Z.; Wang, N.; Chu, W. Improvement of catalytic stability for CO2 reforming of methane by copper promoted Ni-based catalyst derived from layered-double hydroxides. J. Energy Chem. 2016, 25, 1078−1085. (4) Berger, E.; Hahn, M. W.; Przybilla, T.; Winter, B.; Spiecker, E.; Jentys, A.; Lercher, J. A. Impact of solvents and surfactants on the selfassembly of nanostructured amine functionalized silica spheres for CO2 capture. J. Energy Chem. 2016, 25, 327−335. (5) Huang, K.; Sun, C.-L.; Shi, Z.-J. Transition-metal-catalyzed C-C bond formation through the fixation of carbon dioxide. Chem. Soc. Rev. 2011, 40, 2435−2452. (6) Maeda, C.; Miyazaki, Y.; Ema, T. Recent progress in catalytic conversions of carbon dioxide. Catal. Sci. Technol. 2014, 4, 1482− 1497. (7) Wu, Z.; Xie, H.; Yu, X.; Liu, E. Lignin-Based Green Catalyst for the Chemical Fixation of Carbon Dioxide with Epoxides To Form Cyclic Carbonates under Solvent-Free Conditions. ChemCatChem 2013, 5, 1328−1333. (8) Riduan, S. N.; Zhang, Y. Recent developments in carbon dioxide utilization under mild conditions. Dalton Trans. 2010, 39, 3347−3357. (9) Nguyen, D. S.; Cho, J. K.; Shin, S. H.; Mishra, D. K.; Kim, Y. J. Reusable Polystyrene-Functionalized Basic Ionic Liquids as Catalysts for Carboxylation of Amines to Disubstituted Ureas. ACS Sustainable Chem. Eng. 2016, 4, 451−460. (10) Wang, W. L.; Wang, Y. Q.; Li, C. Y.; Yan, L.; Jiang, M.; Ding, Y. J. State-of-the-Art Multifunctional Heterogeneous POP Catalyst for Cooperative Transformation of CO2 to Cyclic Carbonates. ACS Sustainable Chem. Eng. 2017, 5, 4523−4528. (11) Teffahi, D.; Hocine, S.; Li, C. J. Synthesis of Oxazolidinones, Dioxazolidinone and Polyoxazolidinone (A New Polyurethane) Via A Multi Component-Coupling of Aldehyde, Diamine Dihydrochloride, Terminal Alkyne and CO2. Lett. Org. Chem. 2012, 9, 585−593. (12) Sneddon, G.; Greenaway, A.; Yiu, H. H. P. The Potential Applications of Nanoporous Materials for the Adsorption, Separation, and Catalytic Conversion of Carbon Dioxide. Adv. Energy Mater. 2014, 4, 1301873−1301891. (13) Fenner, S.; Ackermann, L. C−H carboxylation of heteroarenes with ambient CO2. Green Chem. 2016, 18, 3804−3807. (14) Trost, B. M.; Toste, F. D.; Greenman, K. Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion. J. Am. Chem. Soc. 2003, 125, 4518−4526. (15) Manjolinho, F.; Arndt, M.; Goossen, K.; Goossen, L. J. Catalytic C-H Carboxylation of Terminal Alkynes with Carbon Dioxide. ACS Catal. 2012, 2, 2014−2021. (16) Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp(2) carbon. Org. Lett. 2008, 10, 945−948. (17) Jia, W.; Jiao, N. Cu-Catalyzed Oxidative Amidation of Propiolic Acids Under Air via Decarboxylative Coupling. Org. Lett. 2010, 12, 2000−2003. (18) Yu, D.; Zhang, Y. Copper- and copper-N-heterocyclic carbenecatalyzed C-H activating carboxylation of terminal alkynes with CO2 at ambient conditions. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20184− 20189.

AUTHOR INFORMATION

Corresponding Authors

*Xiaofeng Yang. Fax: +86 411-8468-5940. E-mail: [email protected]. *Yanqiang Huang. Fax: +86 411-8468-5940. E-mail: yqhuang@ dicp.ac.cn. ORCID

Yanqiang Huang: 0000-0002-7556-317X Author Contributions

The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript. Notes

The authors declare no competing financial interest.

■

ACKNOWLEDGMENTS The authors acknowledge the financial support from the National Natural Science Foundation of China (21403218, 21476226, 21503125, 21506204, and 21776269), National Key R&D Program of China (2016YFB0600902), State Grid Cooperation of China (SGRI-DL-71-16-016), Dalian Science Foundation for Distinguished Young Scholars (2016RJ04), and Youth Innovation Promotion Association CAS. The authors 9638

DOI: 10.1021/acssuschemeng.7b02678 ACS Sustainable Chem. Eng. 2017, 5, 9634−9639

Letter

ACS Sustainable Chemistry & Engineering

Copolymerization with Silver Tricyanomethanide. ACS Nano 2016, 10, 3166−3175. (38) Makosch, M.; Lin, W. I.; Bumbalek, V.; Sa, J.; Medlin, J. W.; Hungerbuehler, K.; van Bokhoven, J. A. Organic Thiol Modified Pt/ TiO2 Catalysts to Control Chemoselective Hydrogenation of Substituted Nitroarenes. ACS Catal. 2012, 2, 2079−2081. (39) Zhang, Q.; Zhang, S.; Li, S. Novel Functional Organic Network Containing Quaternary Phosphonium and Tertiary Phosphorus. Macromolecules 2012, 45, 2981−2988. (40) Sun, Q.; Jiang, M.; Shen, Z.; Jin, Y.; Pan, S.; Wang, L.; Meng, X.; Chen, W.; Ding, Y.; Li, J.; Xiao, F.-S. Porous organic ligands (POLs) for synthesizing highly efficient heterogeneous catalysts. Chem. Commun. 2014, 50, 11844−11847. (41) Cano, I.; Chapman, A. M.; Urakawa, A.; van Leeuwen, P. W. N. M. Air-Stable Gold Nanoparticles Ligated by Secondary Phosphine Oxides for the Chemoselective Hydrogenation of Aldehydes: Crucial Role of the Ligand. J. Am. Chem. Soc. 2014, 136, 2520−2528. (42) Llop Castelbou, J.; Breso-Femenia, E.; Blondeau, P.; Chaudret, B.; Castillon, S.; Claver, C.; Godard, C. Tuning the Selectivity in the Hydrogenation of Aromatic Ketones Catalyzed by Similar Ruthenium and Rhodium Nanoparticles. ChemCatChem 2014, 6, 3160−3168. (43) Dhiman, M.; Chalke, B.; Polshettiwar, V. Efficient Synthesis of Monodisperse Metal (Rh, Ru, Pd) Nanoparticles Supported on Fibrous Nanosilica (KCC-1) for Catalysis. ACS Sustainable Chem. Eng. 2015, 3, 3224−3230. (44) Schrader, I.; Warneke, J.; Backenkoehler, J.; Kunz, S. Functionalization of Platinum Nanoparticles with L-Proline: Simultaneous Enhancements of Catalytic Activity and Selectivity. J. Am. Chem. Soc. 2015, 137, 905−912. (45) Han, S.; Feng, Y.; Zhang, F.; Yang, C.; Yao, Z.; Zhao, W.; Qiu, F.; Yang, L.; Yao, Y.; Zhuang, X.; Feng, X. Metal-PhosphideContaining Porous Carbons Derived from an Ionic-Polymer Framework and Applied as Highly Efficient Electrochemical Catalysts for Water Splitting. Adv. Funct. Mater. 2015, 25, 3899−3906. (46) Jiang, H.; Zheng, X. Tuning the chemoselective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines catalyzed by phosphine functionalized ionic liquid stabilized ruthenium nanoparticles. Catal. Sci. Technol. 2015, 5, 3728−3734. (47) McCue, A. J.; McKenna, F.-M.; Anderson, J. A. Triphenylphosphine: a ligand for heterogeneous catalysis too? Selectivity enhancement in acetylene hydrogenation over modified Pd/TiO2 catalyst. Catal. Sci. Technol. 2015, 5, 2449−2459. (48) Chen, G.; Xu, C.; Huang, X.; Ye, J.; Gu, L.; Li, G.; Tang, Z.; Wu, B.; Yang, H.; Zhao, Z.; Zhou, Z.; Fu, G.; Zheng, N. Interfacial electronic effects control the reaction selectivity of platinum catalysts. Nat. Mater. 2016, 15, 564−569. (49) Ernst, J. B.; Muratsugu, S.; Wang, F.; Tada, M.; Glorius, F. Tunable Heterogeneous Catalysis: N-Heterocyclic Carbenes as Ligands for Supported Heterogeneous Ru/K-Al2O3 Catalysts To Tune Reactivity and Selectivity. J. Am. Chem. Soc. 2016, 138, 10718− 10721. (50) Banerjee, A.; Dick, G. R.; Yoshino, T.; Kanan, M. W. Carbon dioxide utilization via carbonate-promoted C-H carboxylation. Nature 2016, 531, 215−219. (51) Jover, J.; Maseras, F. Computational characterization of the mechanism for coinage-metal-catalyzed carboxylation of terminal alkynes. J. Org. Chem. 2014, 79, 11981−11987.

(19) Cheng, H.; Zhao, B.; Yao, Y.; Lu, C. Carboxylation of terminal alkynes with CO2catalyzed by bis(amidate) rare-earth metal amides. Green Chem. 2015, 17, 1675−1682. (20) Yuan, Y.; Chen, C.; Zeng, C.; Mousavi, B.; Chaemchuen, S.; Verpoort, F. Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System. ChemCatChem 2017, 9, 882−887. (21) Liu, X.-H.; Ma, J.-G.; Niu, Z.; Yang, G.-M.; Cheng, P. An Efficient Nanoscale Heterogeneous Catalyst for the Capture and Conversion of Carbon Dioxide at Ambient Pressure. Angew. Chem., Int. Ed. 2015, 54, 988−991. (22) Trivedi, M.; Bhaskaran, B.; Kumar, A.; Singh, G.; Kumar, A.; Rath, N. P. Metal−organic framework MIL-101 supported bimetallic Pd−Cu nanocrystals as efficient catalysts for chromium reduction and conversion of carbon dioxide at room temperature. New J. Chem. 2016, 40, 3109−3118. (23) Finashina, E. D.; Kustov, L. M.; Tkachenko, O. P.; Krasovskiy, V. G.; Formenova, E. I.; Beletskaya, I. P. Carboxylation of phenylacetylene by carbon dioxide on heterogeneous Ag-containing catalysts. Russ. Chem. Bull. 2014, 63, 2652−2656. (24) Molla, R. A.; Ghosh, K.; Banerjee, B.; Iqubal, M. A.; Kundu, S. K.; Islam, S. M.; Bhaumik, A. Silver nanoparticles embedded over porous metal organic frameworks for carbon dioxide fixation via carboxylation of terminal alkynes at ambient pressure. J. Colloid Interface Sci. 2016, 477, 220−229. (25) Zhu, N.-N.; Liu, X.-H.; Li, T.; Ma, J.-G.; Cheng, P.; Yang, G.-M. Composite System of Ag Nanoparticles and Metal-Organic Frameworks for the Capture and Conversion of Carbon Dioxide under Mild Conditions. Inorg. Chem. 2017, 56, 3414−3420. (26) Wu, Z.; Sun, L.; Liu, Q.; Yang, X.; Ye, X.; Hu, Y.; Huang, Y. A Schiff base-modified silver catalyst for efficient fixation of CO2 as carboxylic acid at ambient pressure. Green Chem. 2017, 19, 2080− 2085. (27) Zhang, Y.; Ying, J. Y. Main-Chain Organic Frameworks with Advanced Catalytic Functionalities. ACS Catal. 2015, 5, 2681−2691. (28) Zhang, Y.; Lim, D. S. Synergistic Carbon Dioxide Capture and Conversion in Porous Materials. ChemSusChem 2015, 8, 2606−2608. (29) Li, B.; Gong, R.; Wang, W.; Huang, X.; Zhang, W.; Li, H.; Hu, C.; Tan, B. A New Strategy to Microporous Polymers: Knitting Rigid Aromatic Building Blocks by External Cross-Linker. Macromolecules 2011, 44, 2410−2414. (30) Luo, Y.; Li, B.; Wang, W.; Wu, K.; Tan, B. Hypercrosslinked aromatic heterocyclic microporous polymers: a new class of highly selective CO2 capturing materials. Adv. Mater. 2012, 24, 5703−5707. (31) Li, B.; Guan, Z.; Wang, W.; Yang, X.; Hu, J.; Tan, B.; Li, T. Highly dispersed pd catalyst locked in knitting aryl network polymers for Suzuki-Miyaura coupling reactions of aryl chlorides in aqueous media. Adv. Mater. 2012, 24, 3390−3395. (32) Tan, L.; Tan, B. Research Progress in Hypercrosslinked Microporous Organic Polymers. Huaxue Xuebao 2015, 73, 530−540. (33) Jayakumar, S.; Modak, A.; Guo, M.; Li, H.; Hu, X. P.; Yang, Q. H. Ultrasmall Platinum Stabilized on Triphenylphosphine-Modified Silica for Chemoselective Hydrogenation. Chem. - Eur. J. 2017, 23, 7791−7797. (34) Xie, Y.; Wang, T.-T.; Liu, X.-H.; Zou, K.; Deng, W.-Q. Capture and conversion of CO2 at ambient conditions by a conjugated microporous polymer. Nat. Commun. 2013, 4, 1960−1966. (35) Talapaneni, S. N.; Buyukcakir, O.; Je, S. H.; Srinivasan, S.; Seo, Y.; Polychronopoulou, K.; Coskun, A. Nanoporous Polymers IncorporatingSterically ConfinedN-Heterocyclic Carbenes for Simultaneous CO2Capture and Conversion at Ambient Pressure. Chem. Mater. 2015, 27, 6818−6826. (36) Abrahams, B. F.; Batten, S. R.; Hoskins, B. F.; Robson, R. AgC(CN)(3)-based coordination polymers. Inorg. Chem. 2003, 42, 2654−2664. (37) Chen, Z.; Pronkin, S.; Fellinger, T. P.; Kailasam, K.; Vile, G.; Albani, D.; Krumeich, F.; Leary, R.; Barnard, J.; Thomas, J. M.; PerezRamirez, J.; Antonietti, M.; Dontsova, D. Merging Single-AtomDispersed Silver and Carbon Nitride to a Joint Electronic System via 9639

DOI: 10.1021/acssuschemeng.7b02678 ACS Sustainable Chem. Eng. 2017, 5, 9634−9639