Supporting Information. Metalated mesoporous poly(triphenylphosphine) with azo-functionality: efficient catalysts for CO 2 conversion
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1 Supporting Information Metalated mesoporous poly(triphenylphosphine) with azo-functionality: efficient catalysts for C 2 conversion Zhenzhen Yang, Bo Yu, Hongye Zhang, Yanfei Zhao, Yu Chen, Zhishuang Ma, Guipeng Ji, Xiang Gao, Buxing Han and Zhimin Liu* Beijing National Laboratory for Molecular Sciences, Key Laboratory of Colloid, Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing , PR China; Tel: (+) ; liuzm@iccas.ac.cn Table of contents 1. General experimental methods Synthetic procedures... 2 Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Figure S Scheme S Scheme S Characterization (NMR) of the α-alkylidene cyclic carbonate products Characterization (NMR) of the methylamine products S1
2 1. General experimental methods Materials All reagents and solvents were purchased from commercial sources and were used without further purification, unless indicated otherwise. The monomer P(m-NH 2 Ph) 3 were prepared following procedures reported in the literature (Angew. Chem. Int. Ed. 2009, 48, ). Instrumentation Liquid 1 H NMR spectra was recorded in CDCl 3 (internal reference: 7.26 ppm) on Bruck 400 spectrometer. Liquid 13 C NMR was recorded at MHz in CDCl 3 (internal reference: ppm). Solid-state NMR experiments were performed on a Bruker WB Avance II 400 MHz spectrometer. The 13 C CP/MAS NMR spectra were recorded with a 4-mm double-resonance MAS probe and with a sample spinning rate of 10.0 khz; a contact time of 2 ms (ramp 100) and pulse delay of 3 s were applied. FTIR spectra of the samples were collected on a TENSR 27 FTIR at a resolution of 2 cm -1. The nitrogen adsorption and desorption isotherms were measured at 77 K using a Micromeritics ASAP 2020M system. The samples were outgassed at 120 o C for 8 h before the measurements. Surface areas were calculated from the adsorption data using Langmuir and Brunauer-Emmett-Teller (BET) methods. The pore-size-distribution curves were obtained from the adsorption branches using non-local density functional theory (NLDFT) method. Field emission scanning electron microscopy (SEM) observations were performed on a Hitachi S-4800 microscope operated at an accelerating voltage of 15.0 kv. Transmission electron microscopy (TEM) images were obtained with a JEL JEM-1011 instrument operated at 200 kv. The thermal properties of the materials were evaluated using a thermogravimetric analysis (TGA) instrument (STA PT1600 Linseis) over the temperature range of 25 to 800 C under air atmosphere with a heating rate of 10 C/min. X-ray photoelectron spectroscopy (XPS) was performed on an ESCAL Lab 220i-XL spectrometer at a pressure of ~ mbar (1 mbar = 100 Pa) using Al Ka as the excitation source (hn= ev) and operated at 15 kv and 20 ma. The binding energies were referenced to the C 1s line at ev from adventitious carbon. The loading content of metal species in the catalysts was determined by ICP-AES (VISTA-MPX). 2. Synthetic procedures (1) Synthesis of the monomer P(m-NH 2 Ph) 3 Ref. Angew. Chem. Int. Ed. 2009, 48, S2
3 In a Schlenk tube, PCl 3 (6.3 mmol) and anhydrous THF (25 ml) were introduced. This solution was added dropwise at room temperature to a round-bottom flask equipped with a dry nitrogen inlet containing a solution of 3-[bis(trimethylsilyl)amino]phenylmagnesium chloride in THF (1.0 M, 23 mmol). The system was stirred for 1 h. H 2 (25 ml) and petroleum ether (60 ml) were added. The phases were allowed to separate and the upper organic phase was collected and dried over Na 2 S 4. The solvent was evaporated and the residue was further dried under vacuum (20 o C, 12 h) to yield a pale yellow solid. In a round-bottom flask equipped with a dry nitrogen inlet and a stirrer, the pale yellow solid was dissolved in methanol (15 ml) and THF (20 ml). The flask was equipped with a reflux condenser topped by a dry nitrogen bubbler and the solution was refluxed at 100 o C for 24 h. The solvents were evaporated and the residue was further dried under vacuum (20 o C, 24 h) to yield a white solid. The solid was then washed with petroleum ether (2*15 ml), isopropanol (50 ml) and dried under vacuum (20 o C, 24 h) to yield a finely dispersed white solid (1.1 g, 31%). 1 H NMR (d 6 -DMS, 400 MHz) δ 5.06 (s, 6H), 6.36 (t, 3 J = 7.6 Hz, 3H), 6.51 (d, 3 J = 8.4 Hz, 6H), 6.98 (t, 3 J = 7.2 Hz); 13 C NMR (d 6 -DMS, MHz) δ 114.1, 118.6, 118.8, 120.6, 120.8, 128.6, 128.7, 137.6, 137.7, 148.3, S3
4 (2) Synthesis of the polymer poly(pph 3)-azo Ref. Chem. Commun. 2015, 51, To a mixture of P(m-NH 2 Ph) 3 (0.5 mmol) and NaI (3 mmol) in MeCN (30 ml) was added t-bucl (3 mmol) under N 2 atmosphere at room temperature. The mixture was stirred for 1 h and quenched with aqueous Na 2 S 2 3 (1.0 M, 30 ml). The precipitate was filtered off and washed with distilled H 2, THF, CH 3 H and acetone. After extracted in a Soxhlet extractor with methanol, H 2 and THF for 48 h, it was dried at 120 o C under vacuum for 48 h to yield poly(pph 3 )-azo as a brown powder. Yield: 95%. Elemental analysis data: C 69.97%, H 4.87%, N 13.02%. (3) Synthesis of the polymer poly(pph 3)-azo-Ag/Ru For the synthesis of poly(pph 3 )-azo-ag: In a round-bottom flask equipped with a dry nitrogen inlet and a reflux condenser, AgBF 4 (5.4 mg) was dissolved in 20 ml of THF, and then poly(pph 3 )-azo (300 mg) was added under nitrogen. The mixture was kept stirring for 24 h at 80 o C in dark. The resulting solid was isolated by filtration and washed with THF, and then purified using Soxhlet extraction (THF) for 24 h. poly(pph 3 )-azo-ag was obtained as a brown powder after drying at 100 o C under vacuum for 12 h. Recovery: 93%. Elemental analysis data: C 68.37%, H 4.01%, N 12.87%. For the synthesis of poly(pph 3 )-azo-ru: In a round-bottom flask equipped with a dry nitrogen inlet and a reflux condenser, RuCl 3 3H 2 (38.8 mg) was dissolved in 20 ml of EtH, and then poly(pph 3 )-azo (300 mg) was added under nitrogen. The mixture was kept stirring for 24 h at 100 o C. The resulting solid was isolated by filtration and washed with EtH, and then purified using Soxhlet extraction (EtH) for 24 h. Poly(PPh 3 )-azo-ru was obtained as a dark brown powder after drying at 100 o C under vacuum for 12 h. Recovery: 90%. Elemental analysis data: C %, H 4.31%, N 11.98%. (4) Typical procedures for the synthesis of α- alkylidene cyclic carbonates from propargyl alcohols and C 2 A stainless steel autoclave with a Teflon tube (25 ml inner volume) was purged with C 2 S4
5 to evacuate air, and then poly(pph 3 )-azo-ag (20 mg), propargyl alcohols (0.5 mmol), DBU (0.5 mmol) and THF (2 ml) were added successively. C 2 (1 MPa) was charged in the reactor at room temperature. The autoclave was stirred at 25 o C for 18 h. After reaction, the excess of C 2 was vented. In table 1, the product yields was determined by 1 H NMR (CDCl 3, 400 MHz) using 1,4-bis(chloromethyl)-benzen as an internal standard. In Scheme 2, the products was isolated by column chromatography on silica gel using petroleum ether/ethyl acetate (from 10:1 to 1:1) as eluent and identified by NMR spectra. For catalyst (poly(pph 3 )-azo-ag) recycling, the catalyst was recycled by filtration, washed with 50 ml CH 2 Cl 2, and then dried under vacuum at 40 o C for 24 h. The recycled catalyst was reused for the next run without further purification. For each recyclability test, five parallel experiments have been done, and the yield was taken the average. (5) Typical procedure of the methylation of amines catalyzed by poly(pph 3)-azo-Ru A stainless steel autoclave with a Teflon tube (25 ml inner volume) was purged with C 2 to evacuate air, and then poly(pph 3 )-azo-ru (13.5 mg), N-methylaniline (0.5 mmol, 53.6 mg) PhSiH 3 (4 mmol, mg) and THF (2 ml) were added successively. C 2 (0.5 MPa) was charged in the reactor at room temperature. The autoclave was stirred at 120 o C for 24 h. After reaction, the autoclave was cooling to 0 o C then the excess of gas was vented. The product yields were determined by GC with a flame ionization detector using dodecane as an internal standard and were further identified using GC-MS by comparing retention times and fragmentation patterns with authentic samples. For the substrate scope investigation, the products were isolated by column chromatography on silica gel (eluent: petroleum and dichloromethane, from 10:1 to 1:2) and identified by NMR spectra as shown below. For catalyst recycling, the catalyst was recycled by filtration, washed with THF and ethanol, and then dried under vacuum at 60 o C for 24 h, followed by being reused for the next run. For each recyclability test, five parallel experiments have been done, and the yield was taken the average Transmittance/% cm cm cm-1 PAzo-PP P(m-NH2Ph) Wave number/cm -1 Figure S1. FTIR spectra of poly(pph 3 )-azo and the monomer P(m-NH 2 Ph) 3. The spectra were recorded as KBr pellets. S5
6 Absorbance nm P(m-NH2Ph)3 PAzo-PP Wavelength/nm Figure S2. Solid-state UV-visible spectra of poly(pph 3 )-azo and the monomer P(m-NH 2 Ph) 3. Solid-state 13 C NMR Figure S3. Solid-state 13 C NMR spectra for poly(pph 3 )-azo. S6
7 100 Residual weight/% poly(pph3)-azo-ag poly(pph3)-azo-ru poly(pph3)-azo Temperature/ o C Figure S4. TGA results of poly(pph 3 )-azo, poly(pph 3 )-azo-ag and poly(pph 3 )-azo-ru. 1/[W((P 0 /P)-1)] 1/[W((P 0 /P)-1)] 8.00E E E E E E+00 BET surface area: 2.00E m 2 g E+00 R = C constant = E E E E E-01 Relative Pressure (P/P 0 ) 1.60E E E E E E+00 BET surface area: 4.00E m 2 g E+00 R = C constant = E E E E-01 Relative Pressure (P/P 0 ) 1/[W((P 0 /P)-1)] 1.60E E E E E E+00 BET surface area: 4.00E m 2 g E+00 R = C constant = E E E E-01 Relative Pressure (P/P 0 ) Figure S5. BET plot (P/P 0 = ) of (A) poly(pph 3 )-azo, (B) (A) (C) (B) S7
8 poly(pph 3 )-azo-ag and (C) poly(pph 3 )-azo-ru. Figure S6. SEM image of poly(pph 3 )-azo. 100 nm Figure S7. TEM image of poly(pph 3 )-azo. S8
9 Amount Adsorbed (cm 3 STP/g) Amount Adsorbed (cm 3 STP/g) (A) Relative Pressure (P/P 0 ) (C) Relative Pressure (P/P 0 ) dv(log d) cc/g dv(log d) cc/g (B) Pore Width/nm (D) Pore Width/nm Figure S8. Adsorption (filled) and desorption (empty) isotherms of N 2 at 77 k for (A) poly(pph 3 )-azo-ag and (C) poly(pph 3 )-azo-ru. Pore size distribution curve obtained from the adsorption branches using non-local density functional theory (NLDFT) method for (B) poly(pph 3 )-azo-ag and (D) poly(pph 3 )-azo-ru. C poly(pph 3 )-azo-ag C poly(pph 3 )-azo-ru CPS CPS P N P Ag Ag N Ru Cl kev kev Figure S9. EDS profile of poly(pph 3 )-azo-ag and poly(pph 3 )-azo-ru. S9
10 Counts/s N1s ev Binding Energy/eV ev ev Counts/s P2p ev Binding Energy/eV ev Figure S10. XPS spectra of N1s and P2p for poly(pph 3 )-azo. Counts/s Counts/s N1s ev Ag3d Binding Energy/eV ev ev ev Binding Energy/eV ev Counts/s Counts/s P2p ev Binding Energy/eV Ag3d-recycled ev ev Binding Energy/eV ev Figure S11. XPS spectra of N1s, P2p and Ag3d for poly(pph 3 )-azo-ag and Ag3d for recycled poly(pph 3 )-azo-ag after recycling for 5 times. S10
11 Counts/s Counts/s C1s, Ru3d ev ev ev P2p Binding Energy/eV ev ev Binding Energy/eV ev Counts/s Counts/s N1s Ru3d ev Binding Energy/eV ev ev Binding Energy/eV ev Counts/s Ru3d-recycled ev Binding Energy/eV ev Figure S12. XPS spectra of N1s, P2p and Ru3d for poly(pph 3 )-azo-ru and Ru3d for recycled poly(pph 3 )-azo-ru after reused for 5 times. S11
12 20 nm Figure S13. TEM image for poly(pph 3 )-azo-ru. Figure S14. Product analysis for the reaction system of C 2 with 1a: representative 1 H NMR spectrum (Table 1, entry 6). S12
13 Yield of 2a/% Cycle Figure S15. Recyclability test of poly(pph 3 )-azo-ag for the carboxylative cyclization of propargyl alcohol (1a) with C 2 for the synthesis of α-alkylidene cyclic carbonate (2a). Reaction time: 18 h (black) or 1 h (blue). A B nm Counts Particle size/nm 25 nm Figure S16. TEM image for (A) poly(pph 3 )-azo-ru and (B) poly(pph 3 )-azo-ag after recycling for five times. S13
14 100 Yield of N,N-dimethylaniline/% Cycle Figure S17. Recyclability test of poly(pph 3 )-azo-ru for the methylation of N-methylaniline with C 2 for the synthesis of N,N-dimethylaniline. Reaction time: 24 h (black) or 6 h (blue). Scheme S1. Proposed reaction mechanism for the reaction of propargyl alcohol with C 2 catalyzed by poly(pph 3 )-azo-ag. Firstly, the alcohol, activated by DBU, was reacted with C 2 (activated by azo functionalities) to generate a carbonate intermediate. An intramolecular ring-closing reaction S14
15 was then proceeded on the alkyne, which was activated by the Ag species to afford the corresponding cyclic carbonate with the release of the Ag specices and DBU. Ph SiH 3 = Si-H poly(pph 3 )-azo-ru = Ru H-Si H-Si N H N N + C 2 (activated by azo group) N H 2 N Ru Si H N H H Ru N H Si H Si Ru Si Si N Scheme S2. Proposed reaction mechanism for the methylation of amines with C 2 catalyzed by poly(pph 3 )-azo-ru. Firstly, Azo functionality-activated N-methylaniline could coordinate with C 2 (activated by azo functionalities) to afford the carbamate salt, which was then attacked by the hydrosilane, affording the formylation intermediate in the presence of Ru species. Subsequent hydrosilation of the formamide afforded the methylamine product. 3. Characterization (NMR) of the α-alkylidene cyclic carbonate products 1 H NMR (CDCl 3, 400 MHz) δ 1.59 (s, 6H), 4.31 (d, 3 J = 3.6 Hz, 1H), 4.74 (d, 3 J = 4 Hz, 1H); 13 C NMR (CDCl 3, MHz) δ 27.7, 84.8, 85.5, 151.4, S15
16 1 H NMR (CDCl 3, 400 MHz) δ 0.97 (t, 3 J = 7.6 Hz, 3H), 1.57 (s, 3H), (m, 1H), (m, 1H), 4.25 (d, 3 J = 4 Hz, 1H), 4.79 (d, 3 J = 4 Hz, 1H); 13 C NMR (CDCl 3, MHz) δ 7.3, 26.0, 33.4, 85.7, 87.7, 151.6, S16
17 1 H NMR (CDCl 3, 400 MHz) δ 0.86 (t, 3 J = 6.8 Hz, 3H), (m, 8H), 1.56 (s, 3H), (m, 1H), (m, 1H), 4.25 (d, 3 J = 4 Hz, 1H), 4.77 (d, 3 J = 4 Hz, 1H); 13 C NMR (CDCl 3, MHz) δ 14.2, 22.6, 23.1, 26.5, 29.1, 31.7, 40.6, 85.6, 87.5, 151.7, S17
18 1 H NMR (CDCl 3, 400 MHz) δ (m, 6H), 1.57 (s, 3H), (m, 1H), 4.26 (d, 3 J = 3.6 Hz, 1H), 4.81 (d, 3 J = 4 Hz, 1H); 13 C NMR (CDCl 3, MHz) δ16.2, 16.5, 24.2, 37.1, 86.4, 90.0, 151.9, S18
19 1 H NMR (CDCl 3, 400 MHz) δ 1.97 (s, 3H), 4.47 (d, 3 J = 4 Hz, 1H), 4.94 (d, 3 J = 4 Hz, 1H), (m, 5H); 13 C NMR (CDCl 3, MHz) δ 27.5, 87.3, 88.3, 124.8, 129.0, 129.3, 139.3, 151.3, S19
20 1 H NMR (CDCl 3, 400 MHz) δ (m, 6H), (m, 2H), 4.32 (d, 3 J = 3.6 Hz, 1H), 4.75 (d, 3 J = 4 Hz, 1H); 13 C NMR (CDCl 3, MHz) δ 24.4, 40.8, 85.5, 94.4, 151.6, S20
21 1 H NMR (CDCl 3, 400 MHz) δ (m, 10 H), 4.27 (d, 3 J = 4 Hz, 1H), 4.72 (d, 3 J = 4 Hz, 1H); 13 C NMR (CDCl 3, MHz) δ 21.6, 24.3, 36.4, 85.5, 86.4, 151.4, S21
22 4. Characterization (NMR) of the methylamine products 1 H NMR (CDCl 3, 400 MHz) δ 2.93 (s, 6H), (m, 3H), 7.24 (t, 3 J = 8.4 Hz, 2H); 13 C NMR (CDCl 3, MHz) δ 40.59, , , , S22
23 1 H NMR (CDCl 3, 400 MHz) δ 2.28 (s, 3H), 2.92 (s, 6H), 6.72 (d, 3 J = 8.8 Hz, 2H), 7.08 (d, 3 J = 8.4 Hz, 2H); 13 C NMR (CDCl 3, MHz) δ 20.21, 41.05, , , , S23
24 1 H NMR (CDCl 3, 400 MHz) δ 2.88 (s, 6H), 3.78 (s, 3H), (m, 2H), (m, 2H); 13 C NMR (CDCl 3, MHz) δ 41.81, 55.71, , , , S24
25 1 H NMR (CDCl 3, 400 MHz) δ 2.93 (s, 6H), 6.64 (d, 3J= 8.8 Hz, 2H), 7.17 (d, 3J = 9.2 Hz, 2H); 13 C NMR (CDCl 3, MHz) δ 40.64, , , , S25
26 1 H NMR (CDCl 3, 400 MHz) δ 2.90 (s, 6H), (m, 2H), (m, 2H); 13 C NMR (CDCl 3, MHz) δ 41.37, (d, 3 J = 7.3 Hz), (d, 3 J = 22.0 Hz), , , S26
27 1 H NMR (CDCl 3, 400 MHz) δ 2.27 (s, 6H), 3.45 (s, 2H), (m, 5H); 13 C NMR (CDCl 3, MHz) δ 45.31, 64.36, , , , S27
28 S28
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