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1 Supporting Information for Gold(I) Alkynyls Supported by Mono- and Bidentate NHC Ligands: Luminescence and Isolation of Unprecedented Ionic Complexes Alexander A. Penney, Galina L. Starova, Elena V. Grachova, Vladimir V. Sizov, Mikhail A. Kinzhalov, and Sergey P. Tunik* Saint Petersburg State University, Institute of Chemistry, Saint Petersburg, Universitetsky pr. 26, , Russian Federation. Fax: +7 (812)
2 Table of Contents Figure S1. 1 H NMR spectrum of [NHC-(CH2)3-NHC(AuX)2] (X=Cl, Br) 5 Figure S2. ESI + mass spectrum of [NHC-CH2-NHC(AuX)2] (X=Cl, Br)..6 Figure S3. ESI + mass spectrum of [NHC-(CH2)2-NHC(AuX)2] (X=Cl, Br)..7 Figure S4. Transformation of complex 7 into 4A and 6PF6 monitored by 1 H NMR.8 Figure S5. 1 H NMR spectra of NHC HBr and NHC HPF Figure S6. 1 H NMR spectrum of complex Figure S7. 1 H NMR spectra of complexes 6PF6 and 6Br Figure S8. 1 H NMR spectrum of complex 4A..12 Figure S9. 1 H NMR spectrum of complex 4B...13 Figure S10. 1 H NMR spectrum of complex 4C...14 Figure S11. 1 H NMR spectra of complexes 1A, 2A, and 3A Figure S12. 1 H NMR spectra of complexes 1B, 2B, and 3B Figure S13. 1 H NMR spectra of complexes 1C, 2C, and 3C Figure S C{ 1 H} NMR spectrum of complex 2A. 18 Figure S C{ 1 H} NMR spectrum of complex 3A. 19 Figure S C{ 1 H} NMR spectrum of complex 3B..20 Figure S C{ 1 H} NMR spectrum of complex 3C..21 Figure S18. ESI + mass spectrum of complex 6Br...22 Figure S19. ESI + mass spectrum of complex 6PF Figure S20. ESI mass spectrum of 6PF6.24 Figure S21. ESI + mass spectrum of complex 4A..25 Figure S22. ESI + mass spectrum of complex 4B..26 Figure S23. ESI + mass spectrum of complex 4C..27 Figure S24. ESI + mass spectrum of complex 1A..28 2
3 Figure S25. ESI + mass spectrum of complex 2A.. 29 Figure S26. ESI + mass spectrum of complex 3A.. 30 Figure S27. ESI + mass spectrum of complex 1B. 31 Figure S28. ESI + mass spectrum of complex 2B..32 Figure S29. ESI + mass spectrum of complex 3B.. 33 Figure S30. ESI + mass spectrum of complex 1C..34 Figure S31. ESI + mass spectrum of complex 2C..35 Figure S32. ESI + mass spectrum of complex 3C..36 Figure S33. 1 H NMR spectra of complex 7 and Figure S34. ESI + mass spectrum of complex 7.38 Figure S35. ESI + mass spectrum of complex 8.39 Figure S36. ESI mass spectrum of complex 7.40 Figure S37. ESI mass spectrum of Figure S38. Intermolecular π-stacking in the solid-state structure of complex 7.42 Figure S39. UV/vis spectra of NHC ligand precursors.42 Figure S40. UV/vis spectra of complexes 5, 6PF6, and 6Br 43 Figure S41. UV/vis spectra of alkylalkynyl complexes 1B 4C...44 Figure S42. UV/vis spectra of phenylalkynyl complexes 1A, 2A, 3A, and 4A..45 Figure S43. PXRD pattern of 4A blue..46 Figure S44. Emission spectra of two different batches of crystals of complex 4A..47 Figure S45. PXRD pattern of material in batch 2.48 Figure S46. PXRD pattern of complex 3A...49 Figure S47. Solid-state emission and excitation spectra of 4A blue at rt and 77 K.50 Figure S48. Overlay of the asymmetric units of 4A green at 100 and 260 K..51 Figure S49. Solid-state emission spectra of 1A, 2A, 3A, and 4A green DCM /4A yellow at 77 K.52 Figure S50. Solid-state excitation spectra of 1A, 2A, 3A, and 4A green at 77 K and rt..53 Figure S51. Open and closed structures for complex 3A obtained from DFT calculations 55 Figure S52. Ground-state frontier orbitals of the optimized structure of complex 1A.56 3
4 Figure S53. Ground-state frontier orbitals of the optimized structure of complex 2A.57 Figure S54. Ground-state frontier orbitals of the optimized structure of complex 3A.58 Table S1. Absorption and emission wavelengths obtained from calculations..59 Figure S55. Spin density map for the lowest triplet state of complex 2A Figure S56. Ground-state frontier orbitals of the dimeric unit of 4A green polymorph..61 Figure S57. Ground-state frontier orbitals of the dimeric unit of 4A yellow polymorph.62 Figure S58. Ground-state frontier orbitals of the trinuclear cationic part of complex Table S2. Crystallographic data
5 Figure S1. 1 H NMR spectrum of [NHC-(CH2)3-NHC(AuX)2] (X=Cl, Br) (DMSO-d6, rt). 5
6 Figure S2. ESI + mass spectrum of [NHC-CH2-NHC(AuX)2] (X=Cl, Br). Insets show the experimental isotopic patterns of [C58H48N8BrClAu3] + and [C58H48N8Br2Au3] + (black) along with the calculated ones (red). 6
7 Figure S3. ESI + mass spectrum of [NHC-(CH2)2-NHC(AuX)2] (X=Cl, Br). Insets show the experimental isotopic patterns of [C30H27N4ClAu] + and [C30H27N4BrAu] + (black) along with the calculated ones (red). 7
8 Figure S4. Transformation of complex 7 into 4A and 6PF6 monitored by 1 H NMR (DMSO-d6, rt). 8
9 Figure S5. 1 H NMR spectra of NHC HBr (top) and NHC HPF6 (bottom) (DMSO-d6, rt). 9
10 Figure S6. 1 H NMR spectrum of complex 5 (DMSO-d6, rt). 10
11 Figure S7. 1 H NMR spectra of complexes 6PF6 (top) and 6Br (bottom) (DMSO-d6, rt). 11
12 Figure S8. 1 H NMR spectrum of complex 4A (DMSO-d6, rt). 12
13 Figure S9. 1 H NMR spectrum of complex 4B (DMSO-d6, rt). 13
14 Figure S10. 1 H NMR spectrum of complex 4C (DMSO-d6, rt). 14
15 Figure S11. 1 H NMR spectra of complexes 1A, 2A, and 3A (DMSO-d6, rt). 15
16 Figure S12. 1 H NMR spectra of complexes 1B, 2B, and 3B (DMSO-d6, rt). 16
17 Figure S13. 1 H NMR spectra of complexes 1C, 2C, and 3C (DMSO-d6, rt). 17
18 Figure S C{ 1 H} NMR spectrum of complex 2A (CDCl3, rt). 18
19 Figure S C{ 1 H} NMR spectrum of complex 3A (CDCl3, rt). 19
20 Figure S C{ 1 H} NMR spectrum of complex 3B (DMSO-d6, rt). 20
21 Figure S C{ 1 H} NMR spectrum of complex 3C (CDCl3, rt). 21
22 Figure S18. ESI + mass spectrum of complex 6Br. The inset shows the experimental isotopic pattern of [C30H28N4Au] + (black) along with the calculated one (red). 22
23 Figure S19. ESI + mass spectrum of complex 6PF6. The inset shows the experimental isotopic pattern of [C30H28N4Au] + (black) along with the calculated one (red). 23
24 Figure S20. ESI mass spectrum of 6PF6. 24
25 Figure S21. ESI + mass spectrum of complex 4A. The inset shows the experimental isotopic pattern of [C23H19N2AuNa] + (black) along with the calculated one (red). 25
26 Figure S22. ESI + mass spectrum of complex 4B. The inset shows the experimental isotopic pattern of [C23H25N2OAuNa] + (black) along with the calculated one (red). 26
27 Figure S23. ESI + mass spectrum of complex 4C. The inset shows the experimental isotopic pattern of [C20H21N2OAuNa] + (black) along with the calculated one (red). 27
28 Figure S24. ESI + mass spectrum of complex 1A. The inset shows the experimental isotopic pattern of [C45H34N4Au2Na] + (black) along with the calculated one (red). 28
29 Figure S25. ESI + mass spectrum of complex 2A. The inset shows the experimental isotopic pattern of [C46H36N4Au2Na] + (black) along with the calculated one (red). 29
30 Figure S26. ESI + mass spectrum of complex 3A. The inset shows the experimental isotopic pattern of [C47H38N4Au2Na] + (black) along with the calculated one (red). 30
31 Figure S27. ESI + mass spectrum of complex 1B. The inset shows the experimental isotopic pattern of [C45H46N4O2Au2Na] + (black) along with the calculated one (red). 31
32 Figure S28. ESI + mass spectrum of complex 2B. The inset shows the experimental isotopic pattern of [C46H48N4O2Au2Na] + (black) along with the calculated one (red). 32
33 Figure S29. ESI + mass spectrum of complex 3B. The inset shows the experimental isotopic pattern of [C47H50N4O2Au2Na] + (black) along with the calculated one (red). 33
34 Figure S30. ESI + mass spectrum of complex 1C. The inset shows the experimental isotopic pattern of [C39H38N4O2Au2Na] + (black) along with the calculated one (red). 34
35 Figure S31. ESI + mass spectrum of complex 2C. The inset shows the experimental isotopic pattern of [C40H40N4O2Au2Na] + (black) along with the calculated one (red). 35
36 Figure S32. ESI + mass spectrum of complex 3C. The inset shows the experimental isotopic pattern of [C41H42N4O2Au2Na] + (black) along with the calculated one (red). 36
37 Figure S33. 1 H NMR spectra of complex 7 (green) and 8 (red) (DMSO-d6, rt). The spectrum of 6Br is shown in blue for comparison. Note that for 8, a slight contamination with in situ formed complex 4C is observed. 37
38 Figure S34. ESI + mass spectrum of complex 7. The inset shows the experimental isotopic pattern of [C30H28N4Au] + (black) along with the calculated one (red). 38
39 Figure S35. ESI + mass spectrum of complex 8. The inset shows the experimental isotopic pattern of [C30H28N4Au] + (black) along with the calculated one (red). 39
40 Figure S36. ESI mass spectrum of complex 7. The inset shows the experimental isotopic pattern of [C16H10Au] (black) along with the calculated one (red). 40
41 Figure S37. ESI mass spectrum of 8. The inset shows the experimental isotopic pattern of [C10H14O2Au] (black) along with the calculated one (red). 41
42 Figure S38. A fragment of the infinite one-dimensional chain of interpenetrated π-π-linked cations in the solid-state structure of complex 7. Hydrogen atoms and PF6 anions are omitted for clarity. Normalized Absorbance NHC HBr NHC CH 2 NHC 2HBr NHC (CH 2 ) 2 NHC 2HBr NHC (CH 2 ) 3 NHC 2HBr Wavelength (nm) Figure S39. UV/vis spectra of NHC ligand precursors (NHC HBr in CH2Cl2, the rest in MeOH). 42
43 Normalized Absorbance 5 6PF 6 6Br Wavelength (nm) Figure S40. UV/vis spectra of complexes 5, 6PF6, and 6Br in CH2Cl2. 43
44 Normalized Absorbance 4B 4C 1B 2B 3B 1C 2C 3C Wavelength (nm) Figure S41. UV/vis spectra of alkylalkynyl complexes 1B 4C in CH2Cl2. 44
45 Normalized Absorbance 4A 1A 2A 3A Wavelength (nm) Figure S42. UV/vis spectra of phenylalkynyl complexes 1A, 2A, 3A, and 4A in CH2Cl2. 45
46 Experimental pattern Calculated pattern of 4A blue Theta (deg) Figure S43. PXRD pattern of 4A blue. 46
47 Normalized Emission Intensity (a.u.) Batch 1 Batch Wavelength (nm) Figure S44. Room-temperature emission spectra of two different batches of crystals of complex 4A. Batch 1 is comprised mostly of 4A green, batch 2 is formulated as a mixture of 4A green DCM and 4A yellow. Excitation wavelength is 350 nm. 47
48 Sum of the calculated patterns of 4A yellow green DCM and 4A Experimental pattern Theta (deg) Figure S45. PXRD pattern of material in batch 2, formulated as a mixture of 4A green DCM and 4A yellow. 48
49 Experimental pattern Calculated pattern of 3A Theta (deg) Figure S46. PXRD pattern of complex 3A. 49
50 Normalized Emission Intensity (a.u.) 350 nm Excitation (rt) 310 nm Excitation (rt) 350 nm Excitation (77 K) 310 nm Excitation (77 K) rt 77 K Wavelength (nm) Figure S47. Solid-state emission (solid line) and excitation (dashed line) spectra of 4A blue at room temperature and 77 K. 50
51 Figure S48. Overlay of the asymmetric units of 4A green at 100 and 260 K. 51
52 Normalized Emission Intensity (a.u.) 4A green DCM /4A yellow Excitation at 310 nm 4A green DCM /4A yellow Excitation at 350 nm 1A Excitation at 310 nm 1A Excitation at 350 nm 2A Excitation at 310 nm 2A Excitation at 350 nm 3A Excitation at 310 nm 3A Excitation at 350 nm Wavelength (nm) Figure S49. Solid-state emission spectra of 1A, 2A, 3A, and 4A green DCM /4A yellow under 310 and 350 nm excitation at 77 K. 52
53 Normalized Emission Intensity (a.u.) 4A green 77 K 4A green rt 1A 77 K 1A rt 2A 77 K 2A rt 3A 77 K 3A rt Wavelength (nm) Figure S50. Solid-state excitation spectra of 1A, 2A, 3A, and 4A green at 77 K and room temperature. 53
54 lowest-energy open structure open structure, +4.6 kj/mol open structure, +5.1 kj/mol 54
55 closed structure, kj/mol Figure S51. Open and closed structures for complex 3A obtained from DFT calculations. 55
56 HOMO 1 HOMO LUMO LUMO+1 Figure S52. Ground-state frontier orbitals of the optimized structure of complex 1A. 56
57 HOMO 1 HOMO LUMO LUMO+1 Figure S53. Ground-state frontier orbitals of the optimized structure of complex 2A. 57
58 HOMO 1 HOMO LUMO LUMO+1 Figure S54. Ground-state frontier orbitals of the optimized structure of complex 3A. 58
59 Table S1. Absorption and emission wavelengths obtained from DFT and TDDFT calculations. Absorption: energy of the lowest singlet state with high oscillator strength observed in TDDFT calculations. Emission: energy gap between the lowest triplet state and the singlet ground state obtained from DFT geometry optimizations. Experimental values are taken from Table 1. Complex Absorption, nm Emission, nm Experiment Calculation Experiment Calculation (solution) 5 281, none 348 1A , A , A , A , B 283, none 375 2B 281, none 333 3B 284, none 333 4B 283, none 312 1C 283, none 336 2C 281, none 338 3C 283, none 333 4C 283, none
60 Figure S55. Spin density map for the lowest triplet state of complex 2A. 60
61 HOMO 1 HOMO LUMO LUMO+1 Figure S56. Ground-state frontier orbitals of the dimeric unit of 4A green polymorph. 61
62 HOMO 1 HOMO LUMO LUMO+1 Figure S57. Ground-state frontier orbitals of the dimeric unit of 4A yellow polymorph. 62
63 HOMO 1 HOMO LUMO LUMO+1 Figure S58. Ground-state frontier orbitals of the trinuclear cationic part of complex 7. 63
64 The solid-state structures of 9 compounds were determined by single crystal X-ray diffraction analyses. For 3A, diffraction data were collected with an Agilent Technologies Excalibur Eos diffractometer at 100 K using monochromated MoKα radiation. Diffraction data for the crystals of all the other compounds were recorded with an Agilent Technologies SuperNova Atlas diffractometer at 100 K (and also at 260 K for 4A green ) using monochromated microfocused CuKα radiation. Empirical absorption correction was applied in the CrysAlisPro 1 program complex using spherical harmonics implemented in SCALE3 ABSPACK scaling algorithm. Using Olex2 2, the structures of 3A, 4A green (both at 100 and 260 K), and 4A green DCM were solved with the ShelXS 3 structure solution program using Direct Methods and refined with the ShelXL 3 refinement package using Least Squares minimisation. All the other structures were solved with the Superflip 4 structure solution program using Charge Flipping and refined with the ShelXL 3 refinement package using Least Squares minimisation. The carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.5Ueq(C) and C H 0.96 Å for the CH3 groups, Uiso(H) set to 1.2Ueq(C) and C H 0.97 Å for the CH2 groups and Uiso(H) set to 1.2Ueq(C) and C H 0.93 Å for the CH groups. The unit cell parameters and refinement characteristics for the crystal structures of the investigated compounds are given in Table S2. The hygroscopic nature of complex 6Br results in the incorporation of 1.75 water molecules per formula unit. For complex 7, high values of the refinement parameters and rather low bond precision in the structural model are due to the low quality of the crystal and severe disorder. Additionally, the crystal underwent changes in the process of the X-ray experiment. Supplementary crystallographic data for this paper have been deposited at the Cambridge Crystallographic Data Centre and can be obtained free of charge via (1) CrysAlisPro, Agilent Technologies, Version (release ). (2) Dolomanov, O. V; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, (3) Sheldrick, G. M. A Short History of SHELX. Acta Crystallogr. Sect. A 2008, 64, (4) Palatinus, L.; Chapuis, G. SUPERFLIP - a Computer Program for the Solution of Crystal Structures by Charge Flipping in Arbitrary Dimensions. J. Appl. Crystallogr. 2007, 40,
65 Table S2. Crystallographic data. Compound 6Br 6PF6 4A blue 4A green (100 K) 4A green (260 K) 4A green DCM 4A yellow Formula C 30H 28N 4AuBr, 1.75H 2O C 30H 28N 4AuPF 6 C 23H 19N 2Au C 23H 19N 2Au C 23H 19N 2Au C 23H 19N 2Au, 0.38CH 2Cl 2 C 23H 19N 2Au Formula weight Temperature (K) 100(2) 100(2) 100(2) 100(2) 260(2) 100(2) 100(2) Crystal system monoclinic triclinic monoclinic monoclinic monoclinic triclinic triclinic Space group P2 1/c P-1 P2/c P2 1/c P2 1/c P-1 P-1 a (Å) (10) (9) (2) (3) (4) (3) (3) b (Å) (3) (12) (6) (2) (2) (5) (5) c (Å) (3) (10) (14) (4) (5) (4) (7) α ( ) (7) (3) (4) β ( ) (10) (7) (6) (19) (2) (3) (4) γ ( ) (9) (3) (4) Volume (Å 3 ) (18) (2) (6) (12) (14) (12) (8) Z ρ calc (mg/mm 3 ) μ (mm -1 ) F(000) Crystal size (mm 3 ) Θ range ( ) 6.74 to to to to to to to Index ranges -10 h k l 34-9 h k l h 26-7 k 6-33 l h 15-7 k l h k 8-26 l h k l 17-6 h k l 15 Reflections collected Independent reflections [R(int) = ] 5313 [R(int) = ] 7008 [R(int) = ] 7510 [R(int) = ] 6222 [R(int) = ] 7601 [R(int) = ] 3571 [R(int) = ] Data/restraints/parameters 21058/0/ /0/ /0/ /0/ /0/ /0/ /0/236 Goodness-of-fit on F Final R indexes [I>2σ(I)] R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = Final R indexes [all data] R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = Largest diff. peak/hole (e Å -3 ) 3.32/ / / / / / /-1.27 CCDC R 1 = Σ F o F c /Σ F o ; 2 wr 2 = {Σ[w(F o F 2 c ) 2 ]/Σ[w(F 2 o ) 2 ]} 1/2 ; w =1/[σ 2 (F 2 o )+(ap) bp], where P = (F o + 2F 2 2 c )/3; S = {Σ[w(F o F 2 c ) 2 ]/(n p)} 1/2, where n is the number of reflections and p is the number of refinement parameters. 65
66 Compound 4C 3A 7 Formula C 20H 21N 2OAu C 47H 38N 4Au 2, CH 2Cl 2 C 76H 66N 8Au 3PF 6 Formula weight Temperature (K) 100(2) 100(2) 100(2) Crystal system triclinic triclinic triclinic Space group P-1 P-1 P-1 a (Å) (6) (4) (12) b (Å) (5) (8) (2) c (Å) (5) (9) (8) α ( ) (4) (5) (10) β ( ) (5) (4) (8) γ ( ) (5) (4) (13) Volume (Å 3 ) (8) (18) (4) Z ρ calc (mg/mm 3 ) μ (mm -1 ) F(000) Crystal size (mm 3 ) Θ range ( ) 9.82 to to to Index ranges -12 h k l h k l 19-8 h k l 14 Reflections collected Independent reflections 3341 [R(int) = ] 9431 [R(int) = ] 7199 [R(int) = ] Data/restraints/parameters 3341/0/ /0/ /35/194 Goodness-of-fit on F Final R indexes [I>2σ(I)] R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = Final R indexes [all data] R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = Largest diff. peak/hole (e Å -3 ) 2.65/ / /-3.89 CCDC R 1 = Σ F o F c /Σ F o ; 2 wr 2 = {Σ[w(F o F 2 c ) 2 ]/Σ[w(F 2 o ) 2 ]} 1/2 ; w =1/[σ 2 (F 2 o )+(ap) bp], where P = (F o + 2F 2 2 c )/3; S = {Σ[w(F o F 2 c ) 2 ]/(n p)} 1/2, where n is the number of reflections and p is the number of refinement parameters. 66
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