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1 Supporting Information Uncovering the role of oxygen atom transfer in Ru-based catalytic water oxidation Dooshaye Moonshiram, 1,2 Yuliana Pineda-Galvan, 1 Darren Erdman, 1 Mark Palenik, 3, Ruifa Zong, 4 Randolph Thummel, 4 Yulia Pushkar 1* 1 Department of Physics, Purdue University, 525 Northwestern Avenue, West Lafayette, IN, Chemical Sciences and Engineering Division, Argonne National Laboratory, 9700 S. Cass Avenue, Lemont,IL, Code 6189, Chemistry Division, Naval Research Laboratory, 4555 Overlook Avenue SW, Washington, DC, Department of Chemistry, University of Houston, Houston, TX, NRC research associate Table of Contents Pg. Additional Materials and Methods 2 Fig. S1 UV-Vis absorbance of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ and after oxidation 3 Fig.S2 EPR spectrum of [Ru(bpy) 2 (bpy-no)] 3+ in ethanol 3 Fig.S3 Fourier transforms of Ru EXAFS of the Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ and simulated 4 FEFF profile from XRD structure Fig. S4 Fourier transforms of Ru EXAFS of initial [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+, 4 [Ru III (NPM)(4-pic) 2 (H 2 O)] 3+ and catalytic mixture with EXAFS fits Fig. S5 Raman spectra of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ in 16 O and 18 O water. 5 Fig. S6 Raman spectra of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ and [Ru III (NPM)(4-pic) 2 (H 2 O)] 3+ 5 together with [Ru III (NPM)(4-pic) 2 (H 2 O)] 3+ in 16 O and 18 O water Fig. S7 Raman spectra of [Ru III (NPM)(4-pic) 2 (H 2 O)] 3+ oxidized with 1, 2 and 3 equiv. of Ce IV 6 Fig. S8 Stopped-flow UV-Vis of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ with excess Ce(IV) 6 Fig. S9 Raman spectra of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ oxidized with 4 equiv. of Ce IV and after melting for 1 min 7 Fig. S10 Raman spectra of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ oxidized with 20 equiv. Ce IV and 20 7 equiv. sodium periodate Fig. S11 X-Band EPR spectrum of 0.5 mm solution of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ after 8 exhaustive bulk electrolysis Fig. S12 Oxygen evolution profiles of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ before and after bulk 8 electrolysis Table S1 Results of DFT calculations for intermediates of [Ru II (NPM)(pic) 2 (OH 2 )] 2+ in the water 9 nucleophilic attack pathway for O-O bond formation. Table S2 Results of DFT calculation for intermediates of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ in the 10 oxygen atom transfer pathway involving non coordinated nitrogen for O-O bond formation. Table S3 EXAFS fits of Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ complex 11 Table S4 EXAFS fits of Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ complex 12 Table S5 EXAFS fits of intermediate generated after oxidation of [Ru II (NPM)(4-pic) 2 (H 2 O)] with 20 equiv of Ce IV and after freezing within 30 sec Table S6 DFT predicted values of Raman vibrations and isotope shifts 14 Table S7 Calculated Cartesian coordinates of intermediates in catalytic cycle 15 S1
2 Additional Materials and Methods Synthesis of [Ru(bpy) 2 (bpy-no)](pf 6 ) 2 The synthesis process of the [Ru(bpy) 2 (bpy-no)](pf 6 ) 2 complex was conducted in the dark or under dim red light due its light sensitivity. 200 mg (0.38 mmol) of [Ru(bpy) 2 Cl 2 ] 2H 2 O were first dissolved in 30 ml of EtOH. 130mg (0.76 mmol) of AgNO 3 was subsequently added to the resulting solution and the mixture was refluxed for around 30 min (The deposited AgCl was separated by filtration). 20 ml of triethyl orthoformate (dehydrating agent) was then added to the resulting solution and the mixture was heated for min at C while continuously stirring.meanwhile, bipyridine-n-oxide ligand (72.3 mg, 0.42 mmol) was dissolved separately in 10 ml of EtOH- triethyl orthoformate (3/2, volume) mixture and warmed for min at C again while continuously stirring. The two solution mixtures were then mixed, stirred for 1 hour at 80 C and reduced to around 1/3 of its volume by by rotor evaporation. In order to precipitate [Ru(bpy) 2 (bpy-no)](pf 6 ) 2, (131 mg, 0.8 mmol) of NH 4 PF 6 was dissolved in 1 ml of the preheated mixture of the EtOH- triethyl orthoformate (3/2, volume),added in solution and kept in the refrigerator at -5 C Crystals were formed overnight, filtered and washed with small amounts of cold ethanol. Due to its light sensitivity, the obtained crystals were stored in the dark during its characterization through mass spectroscopy,nmr and EPR. The EPR spectrum of the resulting [Ru(bpy) 2 (bpy-no)](pf 6 ) 2 solution in ethanol is shown in Figure S1. The properties of this compound are be described in a separate manuscript currently in preparation. S2
3 Figure S1. UV-vis absorbance of starting material [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ and immediate spectra after adding 1, 2,3 eq of Ce(IV) in 0.1 mol HNO 3 Figure S2: EPR spectrum (20K) of [Ru(bpy) 2 (bpy-no)] 3+ in ethanol. S3
4 Figure S3. Fourier transforms of k 3 -weighted Ru EXAFS of the initial Ru II (NPM)(4- pic) 2 (H 2 O)] 2+ and prediction generated from its XRD structure reported in 44 Figure S4. Comparison of the Fourier transforms of experimental k 3 -weighted Ru EXAFS (Figure 5 in the manuscript) of the initial [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ (A); [Ru III (NPM)(4- pic) 2 (H 2 O)] 3+ generated by addition of 1 equiv. of Ce IV (C) and catalytic mixture generated by addition of 20 equiv. of Ce IV and frozen within 30 sec. Dashed lines are representative EXAFS fits from Table S3, S4 and S5 S4
![Figure S5. Comparison of the Raman spectra (77 K) of the initial [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ in 16 O and 18 O water.](/docs-images/72/66281255/images/5-1.jpg "No changes in spectrum observed upon incubating the sample in an 18 O enriched environment.")
5 Figure S5. Comparison of the Raman spectra (77 K) of the initial [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ in 16 O and 18 O water. No changes in spectrum observed upon incubating the sample in an 18 O enriched environment. Figure S6 A) Comparison of the initial [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ and [Ru III (NPM)(4- pic) 2 (H 2 O)] 3+, which was produced by addition of 1 equiv. of Ce IV. B) Comparison of [Ru III (NPM)(4-pic) 2 (H 2 O)] 3+ in 16 O and 18 O water - no major changes were noted. S5
6 Figure S7. A) Comparison of the [Ru III (NPM)(4-pic) 2 (H 2 O)] 3+, which was produced by addition of 1 equiv. of Ce IV and samples generated by addition of 2 and 3 equiv. of Ce IV. S6
7 Figure S8: Stopped-flow Uv-Vis absorbance of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ with excess Ce(IV) monitored over a period of 100 sec.. Stopped-flow UV-Vis kinetics of 0.5 mm [Ru II (L)(4-pic) 2 (OH 2 )] 2+ with excess Ce(IV) in 0.1 mol HNO 3 at nm C. X-band EPR (25K) of 0.5 mm [Ru II (L)(4-pic) 2 (OH 2 )] 2+ oxidized with 20 eq of Ce(IV) in 0.1 mol HNO 3 and freeze-quenched at indicated time intervals in A. S7
8 Figure S9. Comparison of the spectrum of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ oxidized with 4 equiv. of Ce IV and same samples melted for 1 min. Figure S10. Comparison of the spectrum of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ oxidized with 20 equiv. Ce IV and 20 equiv. sodium periodate, 0.1 M HNO 3. S8
9 Figure S11: X-Band EPR spectrum (solid green line) (25K) of 0.5 mm solution of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ after exhaustive bulk electrolyses at potential of Ru II /Ru IV couple. Simulation (dashed line) of the EPR spectrum with g-tensor g xx =2.295, g yy =2.185 and g zz =1.825; linewidths are 6, 7.5 and 10 mt correspondingly. Figure S12: Oxygen evolution profiles of 0.1 mm solution of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ (black) and after exhaustive bulk electrolysis at 1.35V (~0.15V above E 1/2 Ru III /Ru IV couple) (red) upon addition of 50 eq. Ce(IV) in 0.1 mol HNO 3. S9
10 Table S1. Results of DFT calculation for intermediates of [Ru II (NPM)(pic) 2 (OH 2 )] 2+ in the water nucleophilic attack pathway for O-O bond formation. Species; number of explicit water molecules Total charge, Spin multiplicity free energy (H) bond distance (Å) Ru II H 2 O; 2H 2 O 2, Ru OH 2 (2.207) Ru III H 2 O; 2H 2 O a 3, Ru OH 2 (2.053) Ru III OH; 2H 2 O 2, Ru O (1.949) Ru IV =O; 2H 2 O 2, Ru=O (1.804) Ru V =O; 2H 2 O 3, Ru=O (1.731) Ru II OOH; H 2 O 1, Ru O (2.082), O-O (1.467) Ru III OOH; H 2 O 2, Ru O (1.963), O-O (1.409) Ru III OO; H 2 O 1, Ru O (2.081), O-O (1.323) Ru IV OOH; H 2 O 3, Ru-O (2.069), O-O (1.351) Ru IV OO; H 2 O 2, Ru O (2.099), O-O (1.234) Ru V -OO; H 2 O 3, Ru-O (2.002), O-O (1.247) Ru V -OO; H 2 O in reality Ru III -O 2 (oxygen) H 2 O 0, O 2 0, , Ru-O (2.328), O-O (1.214) Elemental steps G 0 /ev a E 0 /V b Redox steps Ru III H 2 O; 2H 2 O + 1e = Ru II H 2 O; 2H 2 O Ru III OH; 2H 2 O + 1e + 1H + = Ru II H 2 O; 2H 2 O Ru IV =O; 2H 2 O + 1e + 2H + = Ru III H 2 O; 2H 2 O Ru V =O; 2H 2 O + 1e = Ru IV =O; 2H 2 O Ru III OOH; H 2 O + H + + 1e = Ru IV =O; 2H 2 O Ru IV OO; H 2 O + H + + 1e = Ru III OOH; H 2 O Ru IV OOH; H 2 O + 1e = Ru III OOH; H 2 O Ru V -OO; H 2 O + 1e = 3 Ru IV -OO; H 2 O Ru V -OO; H 2 O + 1e = 3 Ru IV -OO; H 2 O Protonation steps Ru III OO; H 2 O + H + = Ru III OOH; H 2 O Ru III OH; 2H 2 O + H + = Ru III H 2 O; 2H 2 O O-O bond formation steps Ru IV =O; 2H 2 O = Ru II OOH; H 2 O + H Ru V =O; 2H 2 O = Ru III OOH; H 2 O + H Ru V =O;H 2 O = Ru III -OOH;H, TS=0.383 ev S10
11 Table S2. Results of DFT calculation for intermediates of [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ in the oxygen atom transfer pathway involving non coordinated nitrogen for O-O bond formation. Species; number of explicit water molecules Total charge, Spin multiplicity free energy (H) bond distance (Å) 2, Ru OH 2 (2.10) Ru II (NPM-NO) H 2 O; H 2 O Ru ---O-N (2.62) Ru III (NPM-NO) H 2 O; 3, Ru OH 2 (2.10) H 2 O Ru ---O-N (2.62) Ru III (NPM-NO) OH; H 2 O 2, Ru OH 2 (1.95) Ru ---O-N (2.23) Ru IV (NPM-NO)=O; H 2 O 2, Ru=O (1.78) Ru ---O-N (2.28) Ru II (NPM-NO,NO) 2, Ru ---O-N (2.36) Ru ---O-N (2.91) Ru II (NPM-NO,NO) 2, Ru ---O-N (2.22) Ru ---O-N (2.44) Ru III (NPM-NO,NO); H 2 O 3, Ru ---O-N (2.29) Ru ---O-N (2.37) Ru III (NPM-NO,NO) 3, Ru ---O-N (2.31) Ru ---O-N (2.35) Ru III (NPM-NO,NO) 3, Ru ---O-N (2.16) Ru ---O-N (2.39) Ru IV (NPM-NO,NO) 4, Ru ---O-N (2.10) Ru ---O-N (2.10) Ru IV (NPM-NO,NO) 4, Ru ---O-N (2.26) Ru ---O-N (2.29) Ru III (NPM) O 2 3, Ru---O 2 (2.33) O=O (1.21) Ru V (NPM-NO)=O; H 2 O 3, Ru=O (1.78) Ru ---O-N (2.28) S11
12 Table S3. Structural parameters from EXAFS fits of the initial Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ complex. a EXAFS range Fit # Shell R, Å 2 x 10 3 R-factor Reduced Chi 2 peak 1 1 Ru-N, Ru-N, * Ru-N, Ru-N, * Ru-O, Ru-N, * Ru-N, 4 Ru-O, all 5 Ru-N, Ru-N, 6 Ru-C, Ru-N, 6 Ru-C, 4 Ru-C, 6 8 Ru-N, 1 Ru-N, 5 Ru-C, 4 Ru-C, 6 9 Ru-N, 1 Ru-N, 5 Ru-C, 4 Ru-C, 6 Ru-N, 2 10 Ru-N, 1 Ru-N, 4 Ru-O, 1 Ru-C, 4 Ru-C, 6 Ru-N, * 2.8* 3.9* 3.9* 3.3* 3.3* 4.0* 4.0* 0.8* 0.8* 0.8* 1.0* 1.0* 1.0* 1.2* 1.2* 1.2* a Fits were done in q-space. R is the Ru backscatter distance. 2 is Debye Waller factor. R-factor and Reduced Chi 2 are the goodness-of-fit parameters (see SI, XAS/EXAFS Section). S o 2 =1.0 was used in all fits. 2 was set to be the same for first shell. Second shell was fitted with one 2. S12
13 Table S4. Structural parameters from EXAFS fits of the initial Ru III (NPM)(4-pic) 2 (H 2 O)] 3+ complex. a EXAFS range Fit # Shell R, Å 2 x 10 3 R-factor Reduced Chi 2 peak 1 1 Ru-N, all 2 Ru-N, Ru-N, 6 Ru-C, 10 4 Ru-N, 1 Ru-N, 6 Ru-C, 10 5 Ru-N, 4 Ru-N, 2 Ru-C, 4 Ru-C, 6 Ru-N, 2 6 Ru-N, 4 Ru-N, 2 Ru-O, 1 Ru-C, 4 Ru-C, 6 Ru-N, * 2.3* * 0.9* 0.2* 0.2* 0.2* 3.1* 3.1* 3.1* 1.9* 1.9* 1.9* a Fits were done in q-space. R is the Ru backscatter distance. 2 is Debye Waller factor. R-factor and Reduced Chi 2 are the goodness-of-fit parameters (see SI, XAS/EXAFS Section). S o 2 =1.0 was used in all fits. 2 was set to be the same for first shell. Second shell was fitted with one 2. S13
14 Table S5. Structural parameters from EXAFS fits of the sample produced by oxidation of the [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ with 20 equiv of Ce IV and freezing within 30 sec. a EXAFS range Fit # Shell R, Å 2 x 10 3 R-factor Reduced Chi 2 peak 1 1 Ru-N, Ru-O, * Ru-N, Ru-O, * Ru-N, 1 Ru-N, Ru-O, Ru-N, all 5 Ru-N, Ru-N, 6 Ru-C, Ru-N, 6 Ru-O, 1 Ru-C, 10 7 Ru-O, 1 Ru-N, 5 Ru-O, 1 Ru-C, 10 8 Ru-O, 1 Ru-N, 5 Ru-O, 1 Ru-C, 10 9 Ru-O, 1 Ru-N, 5 Ru-O, 2 Ru-C, Ru-O, 1 Ru-N, 5 Ru-O, 2 Ru-C, 8 Ru-C, * 4.2* * 3.6* 3.6* * 3.8* * 4.1* 7.0* 7.0* a Fits were done in q-space. R is the Ru backscatter distance. 2 is Debye Waller factor. R-factor and Reduced Chi 2 are the goodness-of-fit parameters (see SI, XAS/EXAFS Section). S o 2 =1.0 was used in all fits. 2 was set to be the same for first shell. Second shell was fitted with one 2. S14
15 Table S6. Summary of DFT predicted values of Raman vibrations and isotope shifts Species* DFT prediction [Ru IV (NPM)=O] 2+ Ru=O, 780 cm -1 (-37 cm -1 ) [Ru III (NPM)OOH] 2+ Ru-O, 530 cm -1 [Ru IV (NPM)O 2 ] 2+ [Ru III -O 2 - ] [Ru V (NPM)(4-pic) 2 O 2 ] 3+ [Ru III -O 2 ] [Ru III (NPM-NO)H 2 O] 3+ [Ru IV (NPM-NO)=O] 2+ [Ru III (NPM-NO,NO)] * all complexes have two 4-pic axial ligands (-21 cm -1 ) O-O, 918 cm -1 (-44 cm -1 ) Ru-O, multiple complex bands below 400 cm -1 O-O, 1442 cm -1 (-83 cm -1 ) O-O, 1611 cm -1 (-92 cm -1 ) See Figure 6 for multiple bands undergoing 16 O/ 18 O isotope shifts + Note that DFT computed regular Raman (not RR) gives information on peak positions and isotope shifts but not on peak intensities. S15
16 Table S7. Calculated Cartesian coordinates of intermediates in catalytic cycle of [Ru II (NPM)(4- pic) 2 (H 2 O)] 2+. [Ru II (NPM)(4-pic) 2 (H 2 O)] 2+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C C N S16
17 C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O S17
18 H H [Ru III (NPM)(4-pic) 2 (H 2 O)] 3+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C S18
19 C N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S19
20 H O H H [Ru III (NPM-NO)(4-pic) 2 (H 2 O)] 3+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C S20
21 C C C N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S21
22 H O H H [Ru III (NPM-NO,NO)(4-pic) 2 (H 2 O)] 3+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C S22
23 C C C N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O S23
24 H H [Ru III (NPM)(4-pic) 2 OOH] 2+ N C C C C C C C C N C N C C C C C N C C C C C C C N Ru O C N C C C C C S24
25 C N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H O H H H H S25
26 H [Ru III (NPM)(4-pic) 2 OH] 2+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C C S26
27 N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H H H S27
28 H H [Ru III (NPM-NO)(4-pic) 2 OH] 2+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C S28
29 C N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H S29
30 H [Ru IV (NPM)(4-pic) 2 (H 2 O)] 2+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C C S30
31 N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H S31
32 H [Ru IV (NPM-NO)(4-pic) 2 (H 2 O)] 2+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C C S32
33 N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H H S33
34 [Ru IV (NPM)(4-pic) 2 (OO)] 2+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C C S34
35 N C C C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H O H H H H H S35
36 [Ru V (NPM)(4-pic) 2 (H 2 O)] 3+ N C C C C C C C C N C N C C C C C N C C C C C C C N Ru O C N C C C C C C N C C S36
37 C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H H O H H S37
38 [Ru V (NPM)(4-pic) 2 (OO)] 3+ C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C C N C C S38
39 C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H H S39
40 C C C N C C N C C C C N C C C C C N C C C C C C C N Ru O C N C C C C C C N C C S40
41 C C C C O H H H H H H H H H H H H H H H H H H H H H H H H H H O H H H H H Ru V =O;H2O to Ru III -OOH;H Transition state S41
42 N C C C C C C C C N C N C C C C C N C C C C C C C N Ru O C N C C C C C C N C C C C C C S42
43 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H H RuIV=O,NO Transition State C C C N C C N C C S43
44 C C N C C C C C N C C C C C C C N Ru O N C C C C C N C C C C C O H H H H H H H H H H H S44
45 H H H H H H H H H H H H S45
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