Supporting Information. Halogen Photoelimination from Monomeric Ni(III) Complexes Enabled by the Secondary Coordination Sphere
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1 Supporting Information Halogen Photoelimination from Monomeric Ni(III) Complexes Enabled by the Secondary Coordination Sphere Seung Jun Hwang, a Bryce L. Anderson, a David C. Powers, a Andrew G. Maher, a Ryan G. Hadt a and Daniel G. Nocera a, * adepartment of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA dnocera@fas.harvard.edu S1
2 Table of Contents Page A. X-Ray Data Analysis... S3 A.1. Structural Data for NiCl 2 (dppb) (9c)... S3 A.2. Structural Data for NiBr 2 (dppe) (9e)... S5 B. Electrochemical Data... S7 C. EPR Spectroscopy... S8 D. Steady-State Photolysis Experiments... S21 E. NMR Data... S29 F. Nanosecond Transient Absorption Spectroscopy... S41 G. Solution Calorimetry Data... S57 H. Computational Details... S60 I.1. XYZ Coordinates... S60 I.2. TD-DFT... S87 I.3. Correlation of Quantum Yield with Computed Ligand Donor Strength... S92 Full Citation for Reference S93 S2
3 A. X-Ray Data Analysis A.1. Structural Data for NiCl 2 (dppb) (9c) Figure S1. Thermal ellipsoid plot of NiCl 2 (dppb) (9c) drawn at the 50% probability level. H-atoms and solvents are omitted for clarity. S3
4 Table S1. X-ray experimental details for NiCl 2 (dppb) (9c) (CCDC ) Crystal Data Chemical formula C 30 H 24 Cl 2 NiP 2 Fw, g/mol Crystal system, space group Monoclinic, Cc Temperature (K) 100(2) a, b, c (Å) (8), (6), (11) α, β, γ ( ) 90, (3), 90 V (Å 3 ) (3) Z 4 Radiation type Cu Kα μ (mm 1 ) Crystal size (mm) Data collection Diffractometer Bruker APEX-II CCD Absorption correction Multi-scan, SADABS T min, T max , No. of measured, independent and observed [I > 2σ(I)] reflections 17647, 3946, 3493 R int (sin θ/λ) max (Å 1 ) Refinement R[F 2 > 2σ(F 2 )], wr(f 2 ), S , , No. of reflections 3946 No. of parameters 317 No. of restraints 2 H-atom treatment H atoms treated by a mixture of independent and constrained refinement Dr max, Dr min (e Å 3 ) 1.258, S4
5 A.2. Structural Data for NiBr 2 (dppe) (9e) Figure S2. Thermal ellipsoid plot of NiBr 2 (dppe) (9e) drawn at the 50% probability level. H-atoms and solvents are omitted for clarity. S5
6 Table S2. X-ray experimental details for complex NiBr 2 (dppe) (9e) (CCDC ) Crystal Data Chemical formula C 14 H 14 BrCl 2 Ni 0.50 P Fw, g/mol Crystal system, space group Monoclinic, P2(1) Temperature (K) 100(2) a, b, c (Å) (11), (7), (12) α, β, γ ( ) 90, (14), 90 V (Å 3 ) (2) Z 4 Radiation type Mo Kα μ (mm 1 ) Crystal size (mm) Data collection Diffractometer Bruker APEX-II CCD Absorption correction Multi-scan, SADABS T min, T max , No. of measured, independent and observed [I > 2σ(I)] reflections 17572, 5280, 4788 R int (sin θ/λ) max (Å 1 ) Refinement R[F 2 > 2σ(F 2 )], wr(f 2 ), S , , No. of reflections 5280 No. of parameters 334 No. of restraints 1 H-atom treatment H atoms treated by a mixture of independent and constrained refinement Dr max, Dr min (e Å 3 ) 1.416, S6
7 B. Electrochemical Data Figure S3. Cyclic voltammogram of 1 mm CH 3 CN solution of NiCl 3 (dppe) (7a), with 0.1 M n Bu 4 PF 6 as the supporting electrolyte. Data was recorded at a scan rate of 100 mv/s with a glassy carbon working electrode, Ag/AgNO 3 reference, and Pt wire counter electrode. S7
8 C. EPR Spectroscopy Figure S4. (a) EPR spectrum of NiCl 3 (dppe) (7a) recorded at 8.0 K in 1:1 CH 3 CN/toluene glass (, black) and simulated (, red). (b) EPR spectra of a frozen solution of NiCl 3 (dppe) (7a) in 1:1 CH 3 CN/toluene obtained at 70.0 K (, black) 35.0 K (, red), 17.5 K (, blue), and 8.0 K (, purple). Inset: plot of intensity at 2997 G versus inverse temperature. S8
9 Figure S5. EPR spectrum of NiCl 3 (dppe-ome) (7a-OMe) recorded at 77 K in 1:1 DCM/toluene glass (, black) and simulated (, red). S9
10 Figure S6. EPR spectrum of NiCl 3 (dppe-cl) (7a-Cl) recorded at 77 K in 1:1 DCM/toluene glass (, black) and simulated (, red). For the simulation, the axial hyperfine, A z, was fixed to 90 MHz and not optimized. S10
11 Figure S7. (a) EPR spectrum of NiCl 3 (dppey) (7b) recorded at 8.0 K in 1:1 CH 3 CN/toluene glass (, black) and simulated (, red). (b) EPR spectra of a frozen solution of NiCl 3 (dppey) (7b) in 1:1 CH 3 CN/toluene obtained at 70.0 K (, black) 35.0 K (, red), 17.5 K (, blue), and 8.0 K (, purple). Inset: plot of intensity at 2999 G versus inverse temperature. S11
12 Figure S8. (a) EPR spectrum of NiCl 3 (dppb) (7c) recorded at 8.0 K in 1:1 CH 3 CN/toluene glass (, black) and simulated (, red). (b) EPR spectra of a frozen solution of NiCl 3 (dppb) (7c) in 1:1 CH 3 CN/toluene obtained at 70.0 K (, black) 35.0 K (, red), 17.5 K (, blue), and 8.0 K (, purple). Inset: plot of intensity at 2990 G versus inverse temperature. S12
13 Figure S9. (a) EPR spectrum of NiCl 3 (dcpe) (7d) recorded at 8.0 K in 1:1 CH 3 CN/toluene glass (, black) and simulated (, red). (b) EPR spectra of a frozen solution of NiCl 3 (dcpe) (7d) in 1:1 CH 3 CN/toluene obtained at 70.0 K (, black) 35.0 K (, red), 17.5 K (, blue), and 8.0 K (, purple). Inset: plot of intensity at 2950 G versus inverse temperature. S13
14 Figure S10. (a) EPR spectrum of NiBr 3 (dppe) (7e) recorded at 8.0 K in 1:1 DCM/toluene glass (, black) and simulated (, red). (b) EPR spectra of a frozen solution of NiBr 3 (dppe) (7e) in 1:1 DCM/toluene obtained at 70.0 K (, black) 35.0 K (, red), 17.5 K (, blue), and 8.0 K (, purple). Inset: plot of intensity at 2970 G versus inverse temperature. S14
15 Figure S11. EPR spectrum of NiBr 3 (dppe) (7e-OMe) recorded at 77.0 K in 1:1 DCM/toluene glass (, black) and simulated (, red). S15
16 Figure S12. EPR spectrum of NiBr 3 (dppe-cl) (7e-Cl) recorded at 77.0 K in 1:1 DCM/toluene glass (, black) and simulated (, red). S16
17 Figure S13. (a) EPR spectrum of NiBr 3 (dppey) (7f) recorded at 8.0 K in 1:1 DCM/toluene glass (, black) and simulated (, red). (b) EPR spectra of a frozen solution of NiBr 3 (dppey) (7f) in 1:1 DCM/toluene obtained at 70.0 K (, black) 35.0 K (, red), 17.5 K (, blue), and 8.0 K (, purple). Inset: plot of intensity at 3025 G versus inverse temperature. S17
18 Figure S14. (a) EPR spectrum of NiBr 3 (dppb) (7g) recorded at 8.0 K in 1:1 DCM/toluene glass (, black) and simulated (, red). (b) EPR spectra of a frozen solution of NiBr 3 (dppb) (7g) in 1:1 DCM/toluene obtained at 70.0 K (, black) 35.0 K (, red), 17.5 K (, blue), and 8.0 K (, purple). Inset: plot of intensity at 2971 G versus inverse temperature. S18
19 Table S3. EPR parameters derived from fitting of NiX 3 (LL) (7) spectra. Compound g x g y g z A z /MHz 7a: NiCl 3 (dppe) a-OMe: NiCl 3 (dppe-ome) a-Cl: NiCl 3 (dppe-cl) b: NiCl 3 (dppey) c: NiCl 3 (dppb) d: NiCl 3 (dcpe) e: NiBr 3 (dppe) e-OMe: NiBr 3 (dppe-ome) e-Cl: NiBr 3 (dppe-cl) f: NiBr 3 (dppey) g: NiBr 3 (dppb) S19
20 Table S4. Selected metrical parameters of NiBr 3 (LL) complexes 7e-7g derived from X-ray diffraction data. LL Ni Br ap (Å) Ni Br basal (Å) P1 Ni P2 ( ) Planarity ( ) a dppe (10) (6) dppey (10) (5) dppb (9) (3) a 360-(two Br ap Ni Br basal + two Br ap Ni P basal ) ( ). S20
21 D. Steady-State Photolysis Experiments Figure S15. (a) Extinction spectra of NiCl 3 (dppe-cl) (7a-Cl) (, black) and NiCl 2 (dppe-cl) (9a-Cl) (, red). (b) Spectral evolution for the photolysis of NiCl 3 dppe-cl (7a-Cl) in MeCN (λ exc > 400 nm). S21
22 Figure S16. (a) Extinction spectra of NiCl 3 (dppey) (7b) (, black) and NiCl 2 (dppey) (9b) (, red). (b) Spectral evolution for the photolysis of complex NiCl 3 (dppey) (7b) in MeCN (λ exc > 400 nm). S22
23 Figure S17. (a) Extinction spectra of NiCl 3 (dppb) (7c) (, black) and NiCl 2 (dppb) (9c) (, red). (b) Spectral evolution for the photolysis of NiCl 3 (dppb) (7c) in MeCN (λ exc > 400 nm). S23
24 Figure S18. (a) Extinction spectra of NiCl 3 (dcpe) (7d) (, black) and NiCl 2 (dcpe) (9d) (, red). (b) Spectral evolution for the photolysis of NiCl 3 (dcpe) (7d) in MeCN (λ exc > 400 nm). S24
25 Figure S19. (a) Extinction spectra of NiBr 3 (dppe) (7e) (, black) and NiBr 2 (dppe) (9e) (, red). (b) Spectral evolution for the photolysis of NiBr 3 (dppe) (7e) in CH 2 Cl 2 (λ exc > 400 nm). S25
26 Figure S20. (a) Extinction spectra of NiBr 3 (dppe-ome) (7e-OMe) (, black) and NiBr 2 (dppe-ome) (9e-OMe) (, red). (b) Spectral evolution for the photolysis of NiBr 3 (dppe-ome) (7e-OMe) in CH 2 Cl 2 (λ exc > 400 nm). S26
27 Figure S21. (a) Extinction spectra of NiBr 3 (dppb) (7g) (, black) and NiBr 2 (dppb) (9g) (, red). (b) Spectral evolution for the photolysis NiBr 3 (dppb) (7g) in CH 2 Cl 2 (λ exc > 400 nm). S27
28 Table S5. UV-vis spectral absorption maxima of LMCT transitions LL NiCl 3 (LL) λ max LMCT / nm NiBr 3 (LL) λ max LMCT / nm dppe 7a 452, 622 7e 472, 682 dppe-ome 7a-OMe 430, 618 7e-OMe 462, 680 dppe-cl 7a-Cl 336, 627 7e-Cl 478, 691 dppey 7b 441, 649 7f 476, 699 dppb 7c 453, 652 7g 479, 715 dcpe 7d 446, 586 S28
29 E. NMR Data Complexes 9b 1 and 9f 2 have been previously reported, but only 31 P{ 1 H} NMR data has been reported. Complexes 9c 3 has been reported in the literature but neither 1 H or 31 P{ 1 H} NMR data have been reported. NiCl 2 (dppe-cl) (9a-Cl): 1 H NMR (600 MHz, CD 2 Cl 2 ) δ (ppm): 7.89 (m, 8H), 7.54 (d, 3 J HH = 7.8 Hz, 8H), 2.15 (d, J HP = 17.4 Hz, 4H); 31 P{ 1 H} NMR (160 MHz, CD 2 Cl 2 ) δ (ppm): 56.7 (s). NiCl 2 (dppey) (9b): 1 H NMR (600 MHz, CD 2 Cl 2 ) δ (ppm): 7.89 (m, 7H), 7.61 (m, 2H), 7.52 (m, 7H), 6.68 (m, 2H); 31 P{ 1 H} NMR (160 MHz, CD 2 Cl 2 ) δ (ppm): 64.7 (s). NiCl 2 (dppb) (9c): 1 H NMR (600 MHz, CD 2 Cl 2 ) δ (ppm): 7.85 (m, 6H), 7.58 (m, 4H), 7.47 (m, 8H), 7.29 (m, 3H), 6.96 (m, 3H); 31 P{ 1 H} NMR (160 MHz, CD 2 Cl 2 ) δ (ppm): 57.3 (s). NiBr 2 (dppe-cl) (9e-Cl): 1 H NMR (600 MHz, CD 2 Cl 2 ) δ (ppm): 7.88 (m, 8H), 7.55(d, 3 J HH = 8.4 Hz, 8H), 2.12 (d, J HP = 17.4 Hz, 4H); 31 P{ 1 H} NMR (160 MHz, CD 2 Cl 2 ) δ (ppm): 65.2 (s). NiBr 2 (dppey) (9f): 1 H NMR (600 MHz, CD 2 Cl 2 ) δ (ppm): 7.90 (m, 8H), 7.60 (m, 3H), 7.52 (m, 4H), 6.83 (m, 2H); 31 P{ 1 H} NMR (160 MHz, CD 2 Cl 2 ) δ (ppm): 73.6 (s). NiBr 2 (dppb) (9g): 1 H NMR (600 MHz, CD 2 Cl 2 ) δ (ppm): 7.75 (m, 4H), 7.62 (m, 8H), 7.25 (m, 10H), 7.00 (m, 4H). 31 P{ 1 H} NMR (160 MHz, CD 2 Cl 2 ) δ (ppm): 65.2 (s). 1 Bomfim, J. A. S.; de Souza, F. P.; Filgueiras, C. A. L.; de Sousa, A. G.; Gambardella, M. T. P. Polyhedron, 2003, 22, Jarrett, P. S.; Sadler, P. J. Inorg. Chem. 1991, 30, Smeets, B. J. J.; Meijer, R. H.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Org. Proc. Res. Dev. 2003, 7, 10. S29
30 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiCl 3 (dppe) (7a) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S30
31 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiCl 3 (dppe-ome) (7a-OMe) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S31
32 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiCl 3 (dppe-cl) (7a-Cl) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S32
33 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiCl 3 (dppey) (7b) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S33
34 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiCl 3 (dppb) (7c) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S34
35 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiCl 3 (dcpe) (7d) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S35
36 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiBr 3 (dppe) (7e) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S36
37 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiBr 3 (dppe-ome) (7e-OMe) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S37
38 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiBr 3 (dppe-cl) (7e-Cl) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S38
39 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiBr 3 (dppey) (7f) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S39
40 Figure S P{ 1 H} NMR spectrum of the reaction solution obtained by photolysis of NiBr 3 (dppb) (7g) with visible light (λ > 400 nm) recorded in CD 2 Cl 2 at 23 C. S40
41 F. Nanosecond Transient Absorption Spectroscopy Figure S33. Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dppe) (7a) (0.44 mm solution in MeCN). (a) Transient absorption spectra recorded at 50 ns (, black), and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8a) calculated from the difference of TA spectra recorded at 50 ns and 50 μs. S41
42 Figure S34. Single wavelength kinetic trace of a MeCN solution of NiCl 3 (dppe) (7a) pumped at 355 nm and recorded at 560 nm. Initial component lifetime: τ = 4.0 ± 0.1 μs. S42
43 Figure S35. Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dppe-ome) (7a-OMe) (0.44 mm solution in MeCN). TA spectra are composites of spectra acquired with windows centered at 450 and 550 nm. (a) Transient absorption spectra recorded at 70 ns (, black), and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8a-OMe) calculated from the difference of TA spectra recorded at 70 ns and 50 μs. S43
44 Figure S36. Single wavelength kinetic trace of a MeCN solution of NiCl 3 (dppe-ome) (7a- OMe) pumped at 355 nm and recorded at 600 nm. Initial component lifetime: τ = 5.3 ± 0.2 μs. S44
45 Figure S37. Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dppe-cl) (7a-Cl) (0.44 mm solution in MeCN). (a) Transient absorption spectra recorded at 70 ns (, black) and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8a-Cl) calculated from the difference of TA spectra recorded at 70 ns and 50 μs. S45
46 Figure S38. Single wavelength kinetic trace of a MeCN solution of NiCl 3 (dppe-cl) (7a-Cl) pumped at 355 nm and recorded at 550 nm. Initial component lifetime: τ = 100 ± 1 ns. S46
47 Figure S39. Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dppey) (7b) (0.44 mm solution in MeCN). (a) Transient absorption spectra recorded at 50 ns (, black), and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8b) calculated from the difference of TA spectra recorded at 50 ns and 50 μs. S47
48 Figure S40. Single wavelength kinetic trace of a MeCN solution of NiCl 3 (dppey) (7b) pumped at 355 nm and recorded at 550 nm. Initial component lifetime: τ = 3.4 ± 0.2 μs. S48
49 Figure S41. Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dppb) (7c) (0.44 mm solution in MeCN). (a) Transient absorption spectra recorded at 300 ns (, black), and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8c) calculated from the difference of TA spectra recorded at 300 ns and 50 μs. S49
50 Figure S42. Single wavelength kinetic trace of a MeCN solution of NiCl 3 (dppb) (7c) pumped at 355 nm and recorded at 550 nm. Initial component lifetime: τ = 6.8 ± 0.1 μs. S50
51 Figure S43. Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dppb) (7c) (0.44 mm solution in 30/70 benzene/mecn). (a) Transient absorption spectra recorded at 300 ns (, black), and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8c) calculated from the difference of TA spectra recorded at 300 ns and 50 μs. S51
52 Figure S44. Single wavelength kinetic trace of a solution (0.44 mm in 30:70 benzene:mecn) of NiCl 3 (dppb) (7c) pumped at 355 nm and recorded at 550 nm. Initial component lifetime: τ = 4.7 ± 0.2 μs. S52
53 Figure S45.Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dcpe) (7d) (0.44 mm solution in MeCN). (a) Transient absorption spectra recorded at 80 ns (, black), and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8d) calculated from the difference of TA spectra recorded at 80 ns and 50 μs. S53
54 Figure S46. Single wavelength kinetic trace of a solution of NiCl 3 (dcpe) (7d) pumped at 355 nm and recorded at 440 nm. Initial component lifetime: τ = 9.8 ± 0.8 μs. S54
55 Figure S47. Transient absorption spectra obtained by laser flash photolysis (355 nm pump) of NiCl 3 (dcpe) (7d) (0.44 mm solution in 30:70 benzene:mecn). (a) Transient absorption spectra recorded at 380 ns (, black), and 50 μs (, red) after laser pulse. (b) Absorption spectrum of the intermediate species (8d) calculated from the difference of TA spectra recorded at 380 ns and 50 μs. S55
56 Figure S48. Single wavelength kinetic trace of a solution (0.44 mm in 30:70 benzene:mecn) NiCl 3 (dcpe) (7d) pumped at 355 nm and recorded at 550 nm. Initial component lifetime: τ = 11.5 ± 0.1 μs. S56
57 G. Solution Calorimetry Data Figure S49. Thermogram for reaction of NiCl 2 (dppey) (9b) with PhICl 2 in CH 2 Cl 2. S57
58 Figure S50. Thermogram for reaction of NiCl 2 (dppb) (9c) with PhICl 2 in CH 2 Cl 2. S58
59 Figure S51. Thermogram for reaction of NiCl 2 (dcpe) (9d) with PhICl 2 in CH 2 Cl 2. S59
60 H. Computational Details H.1. XYZ Coordinates Table S6. Cartesian coordinates of the geometry-optimized NiCl 3 (dppe) (7a). Atom Type x y z Ni Cl Cl Cl P P C C H C H C H C H C H C C H C H C H C H C H C H H C H H S60
61 C C H C H C H C H C H C C H C H C H C H C H S61
62 Table S7. Cartesian coordinates of the geometry-optimized NiCl 3 (dppe- OMe) (7a-OMe). Atom Type x y z Ni Cl Cl Cl P P C C H C H C C H C H C C H C H C C H C H C H H C H H C C H C S62
63 H C C H C H C C H C H C C H C H O O O O C H H H C H H H C H H H C H H H S63
64 Table S8. Cartesian coordinates of the geometry-optimized NiCl 3 (dppe-cl) (7a-Cl). Atom Type x y z Ni Cl Cl Cl P P C C H C H C C H C H C C H C H C C H C H C H H C H H C C H C S64
65 H C C H C H C C H C H C C H C H Cl Cl Cl Cl S65
66 Table S9. Cartesian coordinates of the geometry-optimized NiCl 3 (dppey) (7b). Atom Type x y z Ni Cl Cl Cl P P C H C C H C H C H C H C H C C H C H C H C H C H C H C C H C S66
67 H C H C H C H C C H C H C H C H C H S67
68 Table S10. Cartesian coordinates of the geometry-optimized NiCl 3 (dppb) (7c). Atom Type x y z Ni Cl Cl Cl P P C C H C H C H C H C H C C H C H C H C H C H C C H C H C C H S68
69 C H C H C H C H C C H C H C H C H C H C C H C H S69
70 Table S11. Cartesian coordinates of the geometry-optimized NiCl 3 (dcpe) (7d). Atom Type x y z Ni Cl Cl Cl P P C C H C H C H C H C H C C H C H C H C H C H C H H C H H C C S70
71 H C H C H C H C H C C H C H C H C H C H H H H H H H H H H H H H H H H H H H S71
72 H H H H H H S72
73 Table S12. Cartesian coordinates of the geometry-optimized NiBr 3 (dppe )(7e). Atom Type x y z Ni Br Br Br P P C C H C H C H C H C H C C H C H C H C H C H C H H C H H C C S73
74 H C H C H C H C H C C H C H C H C H C H S74
75 Table S13. Cartesian coordinates of the geometry-optimized NiBr 3 (dppe- OMe) (7e-OMe). Atom Type x y z Ni Br Br Br P P C C H C H C C H C H C C H C H C C H C H C H H C H H C C H C S75
76 H C C H C H C C H C H C C H C H O O O O C H H H C H H H C H H H C H H H S76
77 Table S14. Cartesian coordinates of the geometry-optimized NiBr 3 (dppe- Cl) (7e-Cl). Atom Type x y z Ni Br Br Br P P C C H C H C C H C H C C H C H C C H C H C H H C H H C C H C S77
78 H C C H C H C C H C H C C H C H Cl Cl Cl Cl S78
79 Table S15. Cartesian coordinates of the geometry-optimized NiBr 3 (dppey) (7f). Atom Type x y z Ni Br Br Br P P C H C C H C H C H C H C H C C H C H C H C H C H C H C C H C S79
80 H C H C H C H C C H C H C H C H C H S80
81 Table S16. Cartesian coordinates of the geometry-optimized NiBr 3 (dppb) (7g). Atom Type x y z Ni Br Br Br P P C C H C H C H C H C H C C H C H C H C H C H C C H C H C C H S81
82 C H C H C H C H C C H C H C H C H C H C C H C H S82
83 Table S17. Cartesian coordinates of the geometry-optimized NiCl 3 (dppey) CT complex (8a). Atom Type x y z Ni Cl Cl Cl P P C C H C H C H C H C H C C H C H C H C H C H C H H C H H C C S83
84 H C H C H C H C H C C H C H C H C H C H S84
85 Table S18. Cartesian coordinates of the geometry-optimized NiBr 3 (dppey) CT complex (8e). Atom Type x y z Ni Br Br Br P P C C H C H C H C H C H C C H C H C H C H C H C H H C H H C C S85
86 H C H C H C H C H C C H C H C H C H C H S86
87 H.2. TD-DFT Figure S52. Representative molecular orbitals of NiBr 3 (dppey) (7f). Note that state 7 above consists largely of β156 β171. S87
88 Figure S53. Energy levels of frontier molecular orbitals of NiBr 3 (dppey) (7f). S88
89 Table S19. TD-DFT calculated transitions for NiBr 3 (dppey) (7f), (DCM = CH 2 Cl 2 ). State λ/nm Energy/eV f a Contributions Assignment A 172A (78%) 168A 172A (10%) 169B 172B (29%) 166A 172A (17%) 168A 172A (14%) 165A 172A (48%) 170B 172B (15%) 157A 172A (26%) 169B 172B (21%) 164A 172A (29%) 164B 171B (19%) 157A 172A (12%) 164A 172A (46%) 164B 171B (23%) 156B 171B (30%) 152B 171B (12%) 165B 171B (12%) 157A 172A (18%) 159A 172A (14%) 160A 172B (13%) 165B 172B (11%) 158A 172A (45%) 164B 172B (12%) 158A 172A (16%) 164B 172B (10%) a Calculated transitions with oscillator strengths greater than are listed. α(pσ(ap)) α(d x 2 y2) β(pπ(ap)) β(d x 2 y2) α(phπ) α((d x 2 y2) α(pπ(dis)) α(d x 2 y2) α(phπ) α(d x 2 y2) α(phπ) α(d x 2 y2) β(pσ(ap)) β(d z 2) α(pπ (dis)) α(d x 2 y2) + α(phπ) α(d x 2 y2) α(phπ) α(d x 2 y2) α(phπ) α(d x 2 y2) S89
90 Figure S54. Relevant oscillators (oscillator strength > 0.02; solid black bars) from TD DFT calculations for complex NiBr 3 (dppey) (7f) with simulated absorption spectrum overlaid (solid red line). S90
91 Figure S55. Computational results on the NiX 3 (dppe) CT complexes. (Left) Gas phase TD- DFT calculated absorption spectra for NiCl 3 (dppey) (8a), (black line) and NiBr 3 (dppey) (8e), (red line). (Right) Major molecular orbitals involved in the formation of the absorption features observed around 500 nm for the Cl-based CT complexes. Donor orbitals are along the bottom right, and the acceptor β-lumo is above right. S91
92 H.3. Correlation of Quantum Yield with Computed Ligand Donor Strength Figure S56. Plot of experimental quantum yield versus computed electron donation from the diphosphine backbone to the NiX 3 core. S92
93 Full Citation for Reference 58 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision D.01; Gaussian, Inc.: Wallingford, CT, S93
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