Thermochromic Solid-State Emission of Dipyridyl Sulfoxide Cu(I) Complexes
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1 Supporting Information Thermochromic Solid-State Emission of Dipyridyl Sulfoxide Cu(I) Complexes Christopher M. Brown, Veronica Carta and Michael O. Wolf* Department of Chemistry, University of British Columbia, Vancouver, BC, V6T 1Z1, Canada Table of Contents Characterization Data... 2 NMR Spectra... 4 Powder X-Ray Diffraction Differential Scanning Calorimetry FT-IR Photophysical Properties Crystallographic Information... 25
2 S2 Characterization Data Me-DPS 1 H NMR (400 MHz, CD 2 Cl 2 ) δ 7.50 (t, J = 7.7 Hz, 2H, H 4 ), 7.19 (dt, J = 7.9, 0.8 Hz, 2H, H 3 ), 7.02 (ddd, J = 7.6, 0.9, 0.5 Hz, 2H, H 5 ), 2.50 (s, 6H, H Me ). 13 C{ 1 H} NMR (CD 2 Cl 2, 101 MHz) δ (C 2 ), (C 6 ), (C 4 ), (C 3 ), (C 5 ), (C Me ). HR-ESI MS: Calcd for C 10 H 8 N 2 OSNa: ; Found: [M+Na] +. 1 H NMR (CD 2 Cl 2, 400 MHz): δ (m, 4H, H 3,4 ), (m, 2H, H 5 ), 2.53 (s, 6H, H Me ). 13 C{ 1 H} NMR (CD 2 Cl 2, 101 MHz) δ (C 2 ), (C 6 ), (C 4 ), (C 5 ), (C 3 ), (C Me ). IR (solid): (σ SO) 1037 cm -1. HR-ESI MS: Calcd for C 12 H 12 N 2 OSNa: ; Found: [M+Na] +. Cu-DPSO 10 9 BF O P P Cu 3 N S O N 1 H NMR (CD 3 CN, 400 MHz): δ 8.48 (d, J = 4.8 Hz, 2H, H 6 ), (m, 4H, H 3,5 ), (m, 14H, H 4,9,10 ), (m, 10H, H 8,14 ), 7.00 (td, J = 7.6, 1.1 Hz, 2H, H 13 ), (m, 2H, H 15 ), 6.73 (ddt, J = 6.2, 4.0, 2.4 Hz, 2H, H 12 ). 13 C{ 1 H} NMR (CD 3 CN, 101 MHz) δ (C 1 ), (C 16 ), (C 6 ), (C 5 ), (C 12 ), (t, C 8 ), (C 14 ), (t, C 7 ), (C 10 ), (t, C 9 ), (C 4 ), (C 13 ), (t, C 11 ), (C 15 ), (C 3 ).
3 S3 31 P{ 1 H} NMR (CD 3 CN, 161 MHz): δ HR-ESI MS: Calcd for C 46 H 36 N 2 O 2 P 2 SCu: ; Found: [M BF] +. Anal. Calcd for C 46 H 36 BF 4 N 2 O 2 P 2 SCu: C, 61.86; H, 4.06; N, 3.14; S, Found: C, 61.82; H, 4.23; N, 2.98; S, Cu-Me-DPSO P O P Me Me Cu Me 3 N S O N BF 4 1 H NMR (CD 3 CN, 400 MHz): δ 7.82 (t, J = 7.7 Hz, 2H, H 5 ), 7.70 (d, J = 7.7 Hz, 2H, H 4 ), 7.41 (dt, J = 13.6, 6.8 Hz, 12H, H 8,9 ), (m, 12H, H 8,14,16 ), 6.99 (t, J = 7.5 Hz, 2H, H 13 ), 6.93 (d, J = 8.0 Hz, 2H, H 15 ), 6.71 (dt, J = 7.2, 3.3 Hz, 2H, H 12 ), 2.48 (s, 6H, H Me ). 13 C{ 1 H} NMR (CD 3 CN, 101 MHz) δ (C 1 ), (C 3 ), (C 16 ), (C 5 ), (C 12 ), (t, C 8 ), (C 14 ), (t, C 7 ), (C 10 ), (t, C 9 ), (C 6 ), (C 13 ), (C 11 ), (C 15 ), (C 4 ), (C Me ). 31 P{ 1 H} NMR (CD 3 CN, 161 MHz): δ HR-ESI MS: Calcd for C 48 H 40 N 2 O 2 P 2 SCu: ; Found: [M BF 4 ] +. Anal. Calcd for C 48 H 40 BF 4 N 2 O 2 P 2 SCu: C, 62.85; H, 4.38; N, 3.04; S, Found: C, 62.41; H, 4.41; N, 2.85; S, 3.40.
4 S4 NMR Spectra Figure S1. 1 H NMR spectrum of Me-DPS in CD 2 Cl 2 at 25 C. Figure S2. 13 C{ 1 H} NMR spectrum of Me-DPS in CD 2 Cl 2 at 25 C.
5 S5 Figure S3. 1 H NMR spectrum of Me-DPSO in CD 2 Cl 2 at 25 C. Figure S4. 13 C{ 1 H} NMR spectrum of Me-DPSO in CD 2 Cl 2 at 25 C.
6 S6 Figure S5. 1 H NMR spectrum of Cu-DPSO in CD 3 CN at 25 C. Figure S6. 13 C{ 1 H} NMR spectrum of Cu-DPSO in CD 3 CN at 25 C.
7 S7 Figure S7. 31 P{ 1 H} NMR spectrum of Cu-DPSO in CD 3 CN at 25 C. Figure S8. COSY NMR spectrum of Cu-DPSO in CD 3 CN at 25 C.
8 S8 Figure S9. NOESY NMR spectrum of Cu-DPSO in CD 3 CN at 25 C. Figure S10. HSQC NMR spectrum of Cu-DPSO in CD 3 CN at 25 C.
9 S9 Figure S11. HMBC NMR spectrum of Cu-DPSO in CD 3 CN at 25 C. Figure S12. 1 H NMR spectrum of Cu-Me-DPSO in CD 3 CN at 25 C.
10 S10 Figure S C{ 1 H} NMR spectrum of Cu-Me-DPSO in CD 3 CN at 25 C. Figure S P{ 1 H} NMR spectrum of Cu-Me-DPSO in CD 3 CN at 25 C.
11 S11 Figure S16. COSY NMR spectrum of Cu-Me-DPSO in CD 3 CN at 25 C. Figure S17. NOESY NMR spectrum of Cu-Me-DPSO in CD 3 CN at 25 C.
12 S12 Figure S18. HSQC NMR spectrum of Cu-Me-DPSO in CD 3 CN at 25 C. Figure S19. HSQC NMR spectrum of Cu-Me-DPSO in CD 3 CN at 25 C.
13 S13 Figure S20. Possible binding modes of the diimine ligands in Cu-DPSO and Cu-Me-DPSO. Figure S21. Low temperature NMR spectra of Cu-Me-DPSO in CD 3 CN from 25 C to 40 C.
14 S14 Powder X-Ray Diffraction Figure S22. pxrd of Cu-DPSO compared to the simulated powder pattern generated from the single crystal structure (N,N and N,O bound). Figure S23. pxrd of Cu-DPSO during heating to 180 C.
15 S15 Figure S24. pxrd of Cu-DPSO during cooling to 180 C. Figure S25. pxrd cycle of c-cu-me-dpso cooled from room temperature to 180 C and back to room temperature.
16 S16 Differential Scanning Calorimetry Figure S26. DSC data of (a) Cu-DPSO and (b) Cu-Me-DPSO. Both samples were scanned over a temperature range of C with three cycles.
17 S17 FT-IR Figure S27. FT-IR spectrum of Me-DPSO (neat solid) at 25 C. Figure S28. FT-IR spectrum of Cu-DPSO (neat solid) at 25 C.
18 S18 Figure S29. FT-IR spectra of a-cu-me-dpso (grey) and c-cu-me-dpso (pink) as neat solids at 25 C.
19 S19 Photophysical Properties Figure S30. UV-vis absorption spectra of DPSO (blue trace) and Me-DPSO (red trace) in CH 2 Cl 2 at 25 C. Concentrations ~ M. Figure S31. Normalized excitation (dashed line) and emission (solid line) spectra of DPSO (blue trace) and Me-DPSO (red trace) in CH 2 Cl 2 at 25 C. Concentrations ~ M. λ ex = 310 nm.
20 S20 Figure S32. Absorption spectra of a-cu-me-dpso and c-cu-me-dpso in CH 2 Cl 2 at 25 C. Concentrations ~ M. Figure S33. Excitation spectra Cu-DPSO and Cu-Me-DPSO in CH 2 Cl 2. Concentrations ~ M.
21 S21 Figure S34. Variable temperature solid-state emission spectra of a-cu-me-dpso from 196 to 27 C. Thin film dropcast on quartz glass from MeOH. (λ ex = 380 nm) Figure S35. Variable temperature, solid-state emission lifetimes of c-cu-me-dpso from 196 to 25 C. To maintain accuracy, a 50 µs time range was used for 196 C and 20 µs for 25 C. Longest time component for each complex reported. Thin film dropcast on quartz glass from MeOH. (λ ex = 370 nm)
22 S22 Figure S36. Variable temperature UV-vis absorption spectra of c-cu-me-dpso from 196 to 27 C. Thin film dropcast on quartz glass from MeOH. Figure S37. Variable temperature excitation spectra of c-cu-me-dpso measuring the HE emission at 556 nm. Thin film dropcast on quartz glass from MeOH.
23 S23 Figure S38. Variable temperature excitation spectra of c-cu-me-dpso measuring the LE emission at 658 nm. Thin film dropcast on quartz glass from MeOH. Figure S39. Variable temperature excitation spectra of Cu-DPSO measuring the emission at 524 nm. Thin film dropcast on quartz glass from MeOH.
24 Figure S40. Solid-state emission spectra of the crystallization process from a-cu-me-dpso to c-cu- Me-DPSO. At 87 C (black trace) the thin film shows HE emission, and at 107 C (initial) the LE band has already started to grow in. Over the next 30 min the HE band diminishes and the LE band increases in intensity (pink trace). S24
25 S25 Crystallographic Information Table S1. Selected bond length (Å) and angles ( ) of Cu-DPSO (N,N-bound), Cu-DPSO (N,Obound) and Cu-Me-DPSO (N,O-bound). Cu-DPSO (N,N-bound) Cu-DPSO (N,O-bound) Cu-Me-DPSO (N,Obound) Cu1-N (2) a 2.066(2) (18) Cu1-N (2) Cu1-O (18) (17) Cu1-P (7) b (7) (6) Cu1-P (7) c (7) (5) N11-Cu1-N (8) N1-Cu1-O (8) 83.81(7) P1-Cu1-P (2) d (3) (2) a Cu11-N11; b Cu11-P11; c Cu11-P12; d P11-Cu11-P12.
26 S26 Table S2. Summary of crystallographic data for compounds Cu-DPSO and Cu-Me-DPSO. Cu-DPSO Cu-Me-DPSO Chemical formula 2(C 46 H 36 CuN 2 O 2 P 2 S), 2(BF 4 ) C 48 H 40 CuN 2 O 2 P 2 S, BF 4, CH 2 Cl 2 Formula weight a (Å) (7) (11) b (Å) (14) (14) c (Å) (15) (14) α (deg) (16) (2) β (deg) (16) (2) γ (deg) (15) (2) Unit cell volume (Å 3 ) (5) (4) Temperature (K) Crystal system triclinic triclinic Space group P -1 P -1 Z 2 2 Absorption coefficient (µ/mm -1 ) Total number of reflections Unique reflections Final R 1 values (I > 2σ(I) ) Final wr(f 2 ) values (all data)
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