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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information Phosphorescent Pt(II) complexes bearing a monoanionic C^N^N luminophore and tunable ancillary ligands Marian Hebenbrock, a Linda Stegemann, b Jutta Kösters, a Nikos L. Doltsinis, c Jens Müller a * and Cristian A. Strassert b * a M.Sc. M. Hebenbrock, Dipl.-Ing. J. Kösters, Prof. Dr. J. Müller Institut für Anorganische und Analytische Chemie, Westfälische Wilhelms-Universität Münster, Corrensstraße 28/30, D Münster, Germany b Dr. L. Stegemann, Priv.-Doz. Dr. C. A. Strassert - Physikalisches Institut and Center for Nanotechnology, Westfälische Wilhelms-Universität Münster, Heisenbergstraße 11, D Münster, Germany. c Prof. Dr. N. L. Doltsinis - Institut für Festkörpertheorie and Center for Multiscale Theory and Computation, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Straße 10, D Münster, Germany Table of content Crystal structures Computed absorption spectra Computed emission spectra Computed parameters Computed XYZ coordinates NMR assignments Crystal refinement data Photophysical data S1 - S2 S3 S4 S5 - S7 S7 - S35 S36 - S37 S38 S39- S51
2 Figure S1. Solid-state structure of LH. Displacement ellipsoids are drawn at the 50% probability level. Figure S2. Molecular structure of [LPtCl]. Displacement ellipsoids are drawn at the 50% probability level. S1
3 Figure S3. Molecular structure of the cation of [LPtPy]ClO 4. Displacement ellipsoids are drawn at the 50% probability level and counterion submitted for clarity. Figure S4. Molecular structure of [LPt(CCPh)]. Displacement ellipsoids are drawn at the 50% probability level. S2
4 Figure S5. Experimental and computed absorption spectra of [LPtCl]. Solvent models as indicated; solvent: methanol; temperature: K. S3
5 Figure S6. Experimental and computed emission spectra of [LPtCl]. Solvent models as indicated; solvent: methanol; temperature: 77 K. S4
6 Table S1. Calculated and experimental absorption parameters of [LPtCl]: a Wavelength computed by DFT calculations; b oscillator strength; c molecular orbitals with main contribution to excitation and percentage to mixture; d local maximum in experimental absorption spectra. Excitation Entry λ [nm] a f b Nature λ max [nm] d (contribution) c HOMO-1 LUMO+2 (60%) HOMO LUMO+2 (68%) HOMO-3 LUMO (56%) HOMO LUMO+1 (57%) HOMO-1 LUMO (79%) HOMO-2 LUMO (95%) HOMO LUMO (98%) MLCT/LLCT 234 MLCT/LLCT 263 MC/LMCT/IL 303 MLCT/LLCT MC/LMCT/IL/LLCT 347 MLCT/LLCT MC/LMCT/IL 387 S5
7 Figure S7. Computed molecular orbitals of the transitions during the absorption process at the denoted wavelength (for [LPtCl]); isodensity surface plot value: Table S2. Computed bond lengths (Å) and angles ( ) for S 0 and T 1 in the gas phase and with solvent model for complex [LPtCl]; a solvent model: Pauling, solvent: methanol. S 0 (gas phase) T 1 (gas phase) S 0 (PCM) a T 1 (PCM) a Pt-X Pt-N triazole Pt-N pyridine Pt-C phenyl N pyridine -Pt-X C-Pt-X S6
8 Table S3. Computed 0-0 transition energies for complex [LPtCl] in the gas phase and with solvent model and corresponding transition modes. a Solvent model: Pauling; solvent: methanol. b Experimental emission wavelength. ΔE (0-0, gas phase) ΔE (0-0, PCM) a λ max [ev, nm] b Calculated Calculated Nature Nature (ev, nm) (ev, nm) 2.32, 534 ILCT / LMCT 2.56, 484 ILCT / LMCT 2.50, 500 Compound: [LPtCl]; conditions: gas phase, singlet xyz coordinates C C N C C C C C C C C C Pt Cl C N N N C C C S7
9 C C C C C H H H H H H H H H H H H H H H Compound: [LPtCl]; conditions: gas phase, triplet xyz coordinates C C N C C C C C C C S8
10 C C Pt Cl C N N N C C C C C C C C H H H H H H H H H H H H H H H Compound: [LPtPy]ClO 4 ; conditions: gas phase, singlet S9
11 xyz coordinates C C C C C C C N C C C C C N N N C C C C C C C C Pt N C C C C C H H H H H H H H H H H H H S10
12 H H H H H H H O Cl O O O Compound: [LPt(CCPh)]; conditions: gas phase, singlet xyz coordinates C C C C C C C N C C C C S11
13 C N N N C C C C C C C C Pt C C C C C C C C H H H H H H H H H H H H H H H H H H H H S12
14 Compound: [LPtCl]; conditions: PCM (Methanol, Bondi), singlet xyz coordinates C C C C C C C N C C N N C N C C C C C C C C C C Pt Cl H H H H H H H H S13
15 H H H H H H H Compound: [LPtCl]; conditions: PCM (Methanol, Bondi), triplet xyz coordinates C C C C C C C N C C N N C N C C C C C C C C C S14
16 C Pt Cl H H H H H H H H H H H H H H H Compound: [LPtCl]; conditions: PCM (Methanol, Pauling), singlet xyz coordinates C C C C C C C N C C N N S15
17 C N C C C C C C C C C C Pt Cl H H H H H H H H H H H H H H H Compound: [LPtCl]; conditions: PCM (Methanol, triplet), singlet S16
18 xyz coordinates C C C C C C C N C C N N C N C C C C C C C C C C Pt Cl H H H H H H H H H H H H H H H S17
19 Compound: [LPtCl]; conditions: PCM (Methanol, UA0), singlet xyz coordinates C C C C C C C N C C N N C N C C C C C C C C C C Pt Cl H H H H H H H H S18
20 H H H H H H H Compound: [LPtCl]; conditions: PCM (Methanol, UA0), triplet xyz coordinates C C C C C C C N C C N N C N C C C C C C C C C S19
21 C Pt Cl H H H H H H H H H H H H H H H Compound: [LPtCl]; conditions: PCM (Methanol, UFF), singlet xyz coordinates C C C C C C C N C C N N S20
22 C N C C C C C C C C C C Pt Cl H H H H H H H H H H H H H H H Compound: [LPtCl]; conditions: PCM (Methanol, UFF), triplet S21
23 xyz coordinates C C C C C C C N C C N N C N C C C C C C C C C C Pt Cl H H H H H H H H H H H H H H H S22
24 Compound: [LPtCl]; conditions: gas phase, singlet xyz coordinates C C C C C C C N C C N N C N C C C C C C C C C C Pt Cl H H H H H H S23
25 H H H H H H H H H Compound: [LPtPy] + ; conditions: gas phase, triplet xyz coordinates C N C C C C Pt N C C N N C N C C C S24
26 C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H S25
27 Compound: [LPt(CCPh)]; conditions: PCM (Methanol, Pauling), triplet xyz coordinates C C C C C C C C Pt N C C N N C N C C C C C C C C C C C C S26
28 C C C C C H H H H H H H H H H H H H H H H H H H H Compound: [LPt(CCPh)]; conditions: gas phase, triplet S27
29 xyz coordinates C C C C C C C C Pt N C C N N C N C C C C C C C C C C C C C C C C C H H H H H H H H H H H H S28
30 H H H H H H H H Compound: [LPtPy] + ; conditions: PCM (Methanol, Pauling), triplet xyz coordinates C C C C C C C N C C C C Pt N C C N N S29
31 C C C C C C C N C C C C C H H H H H H H H H H H H H H H H H H H H S30
32 Compound: [LPtPy] + ; conditions: gas phase, singlet xyz coordinates C N C C C C Pt N C C C C C C C N N N C C C C C C C C C C C C S31
33 C H H H H H H H H H H H H H H H H H H H H Compound: [LPtPy] + ; conditions: PCM (Methanol, Pauling), singlet xyz coordinates C C C C C S32
34 C C N C C N N Pt C C C C C C C N C C C C N C C C C C H H H H H H H H H H H H H H H H H H H H S33
35 Compound: [LPt(CCPh)]; conditions: PCM (Methanol, Pauling), singlet xyz coordinates C C C C C C C C Pt N C C N N C N C C C C C C C C C C C C S34
36 C C C C C H H H H H H H H H H H H H H H H H H H H S35
37 NMR assignment N N N 9 N H-NMR (400 MHz, CDCl 3 ): δ (ppm) = 8.20 (s, 1H, H13), 8.14 (dd, J = 7.8, 1.0 Hz, 1H, H10), (m, 2H, H1, H5), 7.82 (t, J = 7.8 Hz, 1H, H9), 7.65 (dd, J = 7.9, 1.0 Hz, 1H, H8), (m, 8H, H2, H3, H4, H16, H17, H18, H19, H20), 5.60 (s, 2H, H14). { 1 H} 13 C-NMR (101 MHz, CDCl 3 ): δ (ppm) = (C7), (C11), (C12), (C6), (C9), (C15), (C17, C19), (C3), (C18), (C2, C4), (C16, C20), (C1, C5), (C3), (C8), (C10), 54.2 (C14) N N N 9 N Pt Cl H-NMR (400 MHz, DMF-d 7 ): δ (ppm) = 9.21 (s, 1H, H13), 8.09 (t, J = 8.0 Hz, 1H, H9), 7.86 (ddd, J = 7.7, 4.6, 1.0 Hz, 2H, H8, H10), 7.71 (dd, J = 7.6, 1.3 Hz, J( 195 Pt, 1 H) = 46.4 Hz), 1H, H5), 7.59 (m, 3H, H2, H16, H20), (m, 3H, H17, H18, H19), 7.17 (td, J = 7.4, 1.5 Hz, 1H, H3), 7.09 (td, J = 7.5, 1.4 Hz, 1H, H4), 5.91 (s, 2H, H14). { 1 H} 13 C-NMR (101 MHz, DMF-d 7 ): δ (ppm) = (C7), (C12), (C11), (C6), (C9), (C1), (C15), (C2), (C3), (C16, C20), (C18), (C17, C19), (C13), (C5), (C4), (C8), (C10), 56.0 (C14). S36
38 N N N 10 9 N Pt ClO N 21 1 H-NMR (400 MHz, DMF-d 7 ): δ (ppm) = 9.22 (s, 1H, H13), (m, 2H, H19), (m, 1H, H21), (m, 1H, H9), (m, 4H, H8, H10, H20), (m 1H, H5), (m, 5H, H16, H17, H18), (m, 2H, H4, H3), (m, 1H, H2), 5.89 (s, 2H, H14). { 1 H} 13 C-NMR (101 MHz, DMF-d 7 ): δ (ppm) = (C7), (C19), (C12), (C11), (C6), (C21), (C9), (C1), (C15), (C2), (C3), (C16), (C18), (C17), (C20), (C13), (C5), (C4), (C8), (C10), 56.6 (C14) N N N N Pt H-NMR (400 MHz, DMSO-d 6 ): δ (ppm) = 9.11 (s, 1H, H13), (m, 1H, H9), (m, 3H, H2, H8, H10), 7.60 (d, J = 7.0 Hz, 1H, H5), (m, 5H, H16, H17, H18), (m, 4H, H22, H23), (m, 3H, H3, H4, H24), 5.81 (s, 2H, H14). { 1 H} 13 C-NMR (101 MHz, DMSO-d 6 ): δ (ppm) = (C7), (C12), (C11), (C6), (C9), (C1), (C2), (C15), (C22), (C3), (C17), (C21), (C18), (C16), (C23), (C13), (C24), (C5), (C6), (C8), (C10), (C20), 54.7 (C14). S37
39 Table S4. Crystallographic data. LH [LPtCl] [LPtPy]ClO 4 [LPt(CCPh)] empirical formula C 20 H 16 N 4 C 20 H 15 ClN 4 Pt C 25 H 20 ClN 5 O 4 Pt C 28 H 20 N 4 Pt formula weight crystal system monoclinic monoclinic monoclinic orthorhombic space group P2 1 /n P2 1 /c C2/c Pbca a, b, c / Å (1), (3), (6) (2), (2), (2) (8), (8), (6) (5), (7), (1) / (2) (3) (1) 90 V / Å (6) (4) (4) (3) Z calcd / g cm (Mo K ) / mm crystal size / mm temperature / K 100(2) 100(2) 153(2) 172(2) min, max / 3.09, , , , dataset 7:7, 14:14, 32:32 16:16, 16:16, 18:18 23:22, 0:29, 0:19 16:16, 21:21, 34:34 tot., uniq. data, R int 24388, 3921, , 5122, , 12479, , 6593, observed data [I > 2 (I)] N ref, N par 3921, , , , 298 R 1, wr 2 [I > 2 (I)] , , , , R 1, wr 2 (all data) , , , , S min. and max. resd. dens. 0.22, , , , 1.22 / e Å 3 CCDC number S38
40 Figure S8: Absorption spectrum of [LPtCl] at room temperature in CH 2 Cl 2. Figure S9: Excitation (black) and Emission (red) spectra of [LPtCl] in aerated (left) and deaerated (right) CH 2 Cl 2 (λ exc = 338nm; λ em =580 nm). S39
41 Figure S10: Excitation (black) and Emission (red) spectra of [LPtCl] in a frozen glassy matrix at 77K (left, CH 2 Cl 2 :MeOH 1:1, λ exc =338 nm; λ em = 570 nm) and in the solid state at room temperature (right, λ exc =338 nm; λ em =570 nm). Figure S11: Left: Time-resolved luminescence decay of [LPtCl] in aerated CH 2 Cl 2 including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. S40
42 Figure S12: Left: Time-resolved luminescence decay of [LPtCl] in deaerated CH 2 Cl 2 including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. Figure S13: Left: Time-resolved luminescence decay of [LPtCl] in a frozen glassy matrix (CH 2 Cl 2 :MeOH 1:1) including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. S41
43 Figure S14: Left: Time-resolved luminescence decay of [LPtCl] in the solid state including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. Table S5: Photophysical data of [LPtCl]. λ abs ± 1(nm) λ exc ± 10 (nm) λ em ± 10 (nm) τ ± 0.01 (µs) Φ ± 0.02 k r ± 0.1 (10 5 s -1 ) k nr ± 0.1 (10 5 s -1 ) aerated deaerated a) K solid a) a) intensity weighted averaged lifetime. S42
44 Figure S15: Absorption spectrum of [LPtPy]ClO 4 at room temperature in CH 2 Cl 2. Figure S16: Excitation (black) and Emission (red) spectra of [LPtPy]ClO 4 in aerated (left) and deaerated (right) CH 2 Cl 2 (λ exc =312 nm; λ em =570 nm). S43
45 Figure S17: Excitation (black) and Emission (red) spectra of [LPtPy]ClO 4 in a frozen glassy matrix at 77K (left, CH 2 Cl 2 :MeOH 1:1, λ exc =312 nm; λ em =570 nm) and in the solid state at room temperature (right, λ exc =312 nm; λ em =570 nm). Figure S18: Left: Time-resolved luminescence decay of [LPtPy]ClO 4 in aerated CH 2 Cl 2 including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. S44
46 Figure S19: Left: Time-resolved luminescence decay of [LPtPy]ClO 4 in deaerated CH 2 Cl 2 including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. Figure S20: Left: Time-resolved luminescence decay of [LPtPy]ClO 4 in a frozen glassy matrix (CH 2 Cl 2 :MeOH 1:1) including the residuals (λ exc = nm, λ em = 510 nm). Right: Fitting parameters including pre-exponential factors and confidence limits. S45
47 Figure S21: Left: Time-resolved luminescence decay of [LPtPy]ClO 4 in a frozen glassy matrix (CH 2 Cl 2 :MeOH 1:1) including the residuals (λ exc = nm, λ em = 600 nm). Right: Fitting parameters including pre-exponential factors and confidence limits. Figure S22: Left: Time-resolved luminescence decay of [LPtPy]ClO 4 in the solid state including the instrument response function and the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. S46
48 Table S6: Photophysical data of [LPtPy]ClO 4. λ abs ± 1(nm) λ exc ± 10 (nm) λ em ± 10 (nm) τ ± 0.01 (µs) Φ ± 0.02 k r ± 0.1 (10 5 s -1 ) k nr ± 0.1 (10 5 s -1 ) aerated deaerated K a) (490 nm) a) (600 nm) solid a) (yellow) 1.12 a) (orange) a) intensity weighted averaged lifetime. Figure S23: Absorption spectrum of [LPt(CCPh)] at room temperature in CH 2 Cl 2. S47
49 Figure S24: Excitation (black) and Emission (red) spectra of [LPt(CCPh)] in aerated (left) and deaerated (right) CH 2 Cl 2 (λ exc =312 nm; λ em = 570 nm). Figure S25: Excitation (black) and Emission (red) spectra of [LPt(CCPh)] in a frozen glassy matrix at 77K (left, CH 2 Cl 2 :MeOH 1:1, λ exc =312 nm; λ em = 570 nm) and in the solid state at room temperature (right, λ exc = 312 nm; λ em = 570 nm). S48
50 Figure S26: Left: Time-resolved luminescence decay of [LPt(CCPh)] in aerated CH 2 Cl 2 including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. Figure S27: Left: Time-resolved luminescence decay of [LPt(CCPh)] in deaerated CH 2 Cl 2 including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. S49
51 Figure S28:Left: Time-resolved luminescence decay of [LPt(CCPh)] in a frozen glassy matrix (CH 2 Cl 2 :MeOH 1:1) including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. Figure S29: Left: Time-resolved luminescence decay of [LPt(CCPh)] in the solid state including the residuals (λ exc = nm). Right: Fitting parameters including pre-exponential factors and confidence limits. S50
52 Table S7: Photophysical data of [LPt(CCPh)]. λ abs ± 1(nm) λ exc ± 10 (nm) λ em ± 10 (nm) τ ± 0.01 (µs) Φ ± 0.02 k r ± 0.1 (10 5 s -1 ) k nr ± 0.1 (10 5 s -1 ) aerated deaerated K a) solid a) a) intensity weighted averaged lifetime. S51
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