Supporting Information Reagents. Physical methods. Synthesis of ligands and nickel complexes.

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1 Supporting Information for Catalytic Water Oxidation by A Bio-inspired Nickel Complex with Redox Active Ligand Dong Wang* and Charlie O. Bruner Department of Chemistry and Biochemistry and Center for Biomolecular Structure and Dynamics, University of Montana, Missoula, MT Reagents. All chemicals are of the highest commercially available purity and were used as received, unless noted otherwise. Water used in all experiments was distilled and deionized by a Nanopure Infinity system from Barnstead. Physical methods. UV-vis spectra were recorded with an Agilent Cary 8454 diode array spectrometer at room temperature. CV and controlled potential bulk electrolysis were performed on a CH Instrument 730E electrochemical workstation in ph buffered aqueous solutions at 25 o C using a Ag/AgCl reference electrode, a glassy carbon or indium tin oxide (ITO, resistance 10 Ω in -2 ) working electrode, and a Pt auxiliary electrode. ph was measured using a ph/ion 510 electrode from Fisher Scientific. O 2 evolution was measured by an Orion Star A213 RDO/DO Clark electrode from Thermo Scientific. 1 H NMR spectra were measured at a Varian VNMRS 400 MHz NMR spectrometer. Crystal structures were collected at a Bruker D8 Venture dual source single crystal diffractometer. Synthesis of ligands and nickel complexes. Ligands L1 and L2 were synthesized according to Scheme S1. 6-mesityl-2-pyridinecarboxaldehyde was synthesized via a reported procedure. 1 (2-pyridylmethyl)[(6-mesityl-2-pyridyl)methyl]amine. A 250 ml round bottom flask with stir bar was charged with 6-mesityl-2-pyridinecarboxaldehyde (0.225 g, 1 mmol) and 2- picolyamine (0.108 g, 1 mmol) dissolved in CH 2 Cl 2 (50 ml). NaBH(OAc) 3 (0.318 g, 1.5 mmol) was added and formed a suspension. The cloudy solution was stirred under Ar for 4 hours. An aqueous solution of NaOH (2 M, 50 ml) was then added to quench the reaction. The formation of bubbles was observed. The organic layer was separated and the aqueous layer was extracted with CH 2 Cl 2 (3 20 ml). The organic layer was then combined and dried over Na 2 SO 4. The solvent was removed to obtain (2- pyridylmethyl)[(6-mesityl-2-pyridyl)methyl]amine as a colorless oil in ~90% yield. The product was used for the subsequential synthesis without further purification. 1 H-NMR (CD 3 Cl): δ 8.53 (d, py-6-h, 1H, J = 4.0 Hz), (m, aromatic-h, 8H), 3.99 (s, py- S1

2 CH 2, 2H), 3.96 (s, py-ch 2, 2H), 2.29 (s, mesityl-4-ch 3, 3H), 2.00 (s, mesityl-2,6-ch 3, 6H). 13 C NMR (CD 3 Cl): δ 159.6, 159.5, 159.3, 149.3, 137.7, 137.4, 136.6, 136.4, 135.7, 128.3, 122.9, 122.2, 121.9, 120.1, 54.8, 54.7, 21.1, HR-ESI-MS for [M+H] + : Calcd , Found L1 was synthesized via a similar procedure used for (2-pyridylmethyl)[(6-mesityl-2- pyridyl)methyl]amine. A 250 ml round bottom flask with stir bar was charged with (2- pyridylmethyl)[(6-mesityl-2-pyridyl)methyl]amine (0.317 g, 1 mmol) and salicylaldehyde (0.122 g, 1 mmol) dissolved in CH 2 Cl 2 (50 ml). NaBH(OAc) 3 (0.318 g, 1.5 mmol) was added and formed a suspension. The cloudy solution was stirred under Ar for 4 hours. An aqueous solution of NaOH (2 M, 50 ml) was then added to quench the reaction. The formation of bubbles was observed. The organic layer was separated and the aqueous layer was extracted with CH 2 Cl 2 (3 20 ml). The organic layer was then combined and dried over Na 2 SO 4. The solvent was removed to obtain a light yellow oil. The oil was further purified by flash chromatography over silica gel using ethyl acetate-hexane (20 : 80) as eluant, yielding a white solid after solvent removal in ~80% yield. 1 H-NMR (CD 3 Cl): δ (s, phenol-h, 1H), 8.61 (d, py-6-h, 1H, J = 4.0 Hz), (m, aromatic-h, 12H), 3.90 (s, py-ch 2, 4H), 3.81 (s, phenol-ch 2, 2H), 2.30 (s, mesityl-4-ch 3, 3H), 1.97 (s, mesityl-2,6-ch 3, 6H). 13 C NMR (CD 3 Cl): δ 159.2, 158.2, 157.9, 157.5, 149.0, 137.6, 137.4, 136.9, 136.8, 135.6, 130.0, 129.0, 128.3, 123.3, 123.2, 122.6, 122.3, 121.2, 118.9, 116.5, 59.5, 59.0, 57.0, 21.1, HR-ESI-MS for [M+H] + : Calcd , Found L2 was synthesized via a similar procedure used for L1. 1 H-NMR (CD 3 Cl): δ (s, phenol-h, 1H), 8.61 (d, py-6-h, 1H, J = 4.0 Hz), (m, aromatic-h, 14H), 3.93 (s, py-ch 2, 4H), 3.86 (s, phenol-ch 2, 2H). 13 C NMR (CD 3 Cl): δ 158.1, 157.8, 157.6, 155.8, 149.1, 137.4, 136.7, 130.0, 129.0, 128.8, 128.7, 123.3, 122.5, 122.3, 121.6, 118.9, 118.6, 116.4, 115.7, 115.5, 59.4, 59.3, HR-ESI-MS for [M+H] + : Calcd , Found Preparation and crystallization of 1. L1 (0.423 g, 1 mmol) and Ni(ClO 4 ) 2 6H 2 O (0.366 g, 1 mmol) were dissolved in 2 ml THF to form a purple solution. Tetrabutylammonium hydroxide (0.80 g, 1 mmol) was then added to yield a green solution. The solution was stirred overnight to yield a pale green precipitate. The solid was collected by filtration, washed with THF, and dried in vacuum to afford Ni II (L1)(H 2 O) 2 (ClO 4 )(C 4 H 4 O) (1) in ~80% yield. Anal. For C 32 H 36 ClNiO 8 N 3 Calcd (Found): C, (55.93); H, 5.30 (5.60); N, 6.14 (6.21). Single crystals of 1 suitable for X-ray crystallography were grown by vapor diffusion of diethyl ether into the CH 3 CN solution of 1 to afford green crystals. 2 was prepared in a yield of ~85% and crystalized via similar procedures used for 1. Anal. For (Ni II -L2) 2 (ClO 4 ) 2 (CH 3 CN) C 52 H 45 Cl 2 F 2 Ni 2 O 10 N 7 Calcd (Found): C, (53.85); H, 3.93 (4.12); N, 8.49 (8.47). S2

3 Electrocatalysis. In general, electrocatalytic water oxidation was carried out in aqueous solutions buffered at a target ph on a three-electrode potentiostat. A glassy carbon working electrode (surface area ~0.07 cm 2 ) was used in a typical CV scan, while an ITO conducting glass (surface area ~7 cm 2 ) was employed in a bulk electrolysis experiment. We applied a potential (e.g. 1.5 V) more positive than the onset potential (1.2 V) determined by CV in the bulk electrolysis, together with the high surface area of the ITO electrode, to ensure fast production of O 2. In a typical measurement of the Faradaic yield, a 50 ml electrolysis cell was filled with buffered aqueous solution containing the electrocatalyst and equipped with three electrodes, the Clark electrode, and a stirring bar. The headspace was negligible. Ar was then bubbled through the solution and the O 2 content was monitored by the Clark electrode. The entire apparatus was sealed when the reading of the Clark electrode reached minimum and became stable. The electrolysis was then turned on and the dissolved O 2 produced was measured and recorded by the Clark electrode. In a typical rinse-test experiment, the working electrode (glassy carbon or ITO) after the corresponding electrochemical experiment (CV or bulk electrolysis) was removed from the original solution, gently rinsed with clean buffer solution used in the original experiment, and quickly air-dried. After these treatments, the working electrode was reused immediately in clean buffer solutions as quickly as possible to test the formation of any heterogeneous layer. (S1) Wang, C.-Y.; Liu, Y.-H.; Peng, S.-M.; Liu, S.-T., J. Organomet. Chem. 2006, 691, S3

4 B(OH) 2 NH 2 O HO OH O O N NH N N Br N N N N N Pd(PPh 3 ) 4, Na 2 CO 3 NaBH(OAc) 3 NaBH(OAc) 3 L1 O NH 2 O HO F N OH F NH N N N N N N F NaBH(OAc) 3 NaBH(OAc) 3 L2 Scheme S1. Synthetic procedures for ligands L1 and L2. Figure S1. 1 H NMR spectrum of L1. S4

5 Figure S2. 1 H NMR spectrum of L2. Figure S3. Crystal structure of 2 with thermal ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity. Selected bond distances: Ni-O1: 2.010(2) Å; Ni-O2: 1.955(2) Å; Ni-N1: 2.040(3) Å; Ni-N2: 2.028(3) Å; Ni-N3: 2.068(3) Å; Ni---Ni: Å. S5

6 Figure S4. UV-vis spectrum of 0.5 mm 1 in CH 3 CN. Inset: magnified region showing the spectrum in the range of nm. Figure S5. UV-vis spectrum of 0.5 mm 1 in 0.1 M Na-Pi buffer at ph 7. Inset: ph titration curve monitored at 296 nm. The red line represents the best fit. S6

7 Figure S6. CVs of 0.5 mm 1 in 0.1 M Na-Pi buffer at ph 7 with a scan rate of 50 mv/s (black), 100 mv/s (red), 200 mv/s (red) and 500 mv/s (purple). Currents are normalized on the basis of the square root of the scan rate. Inset: plot of i cat /i diff vs. 1/ν 1/2. The red line represents the best linear fit according to Eq. 2. Figure S7. Current profile of bulk electrolysis at an applied potential of 1500 mv of buffer background (black), 0.5 mm 1 in 0.1 M Na-Pi buffer at ph 7 (red), and clean buffer using the same ITO working electrode after the red trace was obtained (blue). Inset: theoretical (black), measured (red) and background (blue) O 2 formation during controlled potential electrolysis of 0.5 mm 1 in 0.1 M Na-Pi buffer at ph 7. S7

8 Figure S8. Photograph of the electrolysis setup equipped with the ITO working electrode, reference electrode, auxiliary electrode and the Clark electrode for O2 measurement. The red dye was added into the solution to show that the entire electrolysis cell has a negligible headspace. Figure S9. Photographs (from left to right) of clean ITO glass, the ITO electrode after bulk electrolysis in the solution of 0.5 mm 1 at ph 7 described in the main text, and the ITO electrode after bulk electrolysis in the solution of 0.5 mm Ni(NO3)2 under identical conditions. S8

9 Figure S10. CVs of 0.5 mm Ni(NO 3 ) 2 (black) and 0.5 mm 1 (red) in 0.1 M Na-Pi buffer at ph 7. Scan rate = 100 mv/s. E p,c (1) E p,c (2) E p,a Figure S11. CVs of 0.5 mm 1 in 0.1 M Na-Pi buffer at ph 7 with a return potential of 1600 mv (black) and 1000 mv (red). Scan rate = 100 mv/s. S9

10 Figure S12. Forward CV scans of 0.5 mm 1 in 0.1 M Na-Pi buffer at ph = 7 (black), 8 (red), 9 (blue), 9.8 (purple) and 11 (green). Backward scans are omitted for clarity. Scan rate = 100 mv/s. Inset: plot of the potential measured at -40 ma vs. ph of the solution. The red line represents the best linear fit. Figure S13. Linear sweep voltammograms of 0.5 mm 1 in 0.1 M Na-Pi buffer at ph = 7 (black), 8 (red), 9 (blue), 9.8 (purple) and 11 (green). Scan rate = 10 mv/s. S10

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