Switching of the Photophysical Properties of. Bodipy-derived Trans Bis(tributylphosphine) Pt(II) bisacetylide Complexes with Rhodamine

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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information for: Switching of the Photophysical Properties of Bodipy-derived Trans Bis(tributylphosphine) Pt(II) bisacetylide Complexes with Rhodamine as the Acid-Activatable Unit Poulomi Majumdar, Xiaoneng Cui, Kejing Xu and Jianzhang Zhao* State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, E-208 West Campus, 2 Ling-Gong Road, Dalian , P. R. China. zhaojzh@dlut.edu.cn Web: Table of Contents 1. General.S2 2.0 MR and HR MS spectra..... S3 3.0 UV Vis absorption spectra of the complex in different solvents....s Emission Spectra, decay curve and Cyclic voltammogram of the complexes....s DFT calculations... S The x, y, z coordinates....s25 S1

2 1.0 General Singlet oxygen ( 1 2 ) quantum yields (Φ Δ ) Φ Δ value of the triplet photosensitizers were measured with methylene blue (Φ Δ = 0.57 in dichloromethane) as standard. 39 Quantum yields for singlet oxygen ( 1 2 ) generation in CH 2 Cl 2 were determined by monitoring the photooxidation of 1,3- diphenylisobenzofuran (DPBF) sensitized by the Pt(II) complexes. 1,3- Diphenylisobenzofuran (DPBF) was used as the 1 2 scavenger, due to its fast reaction with 1 2. The absorbance of DPBF was adjusted to around 1.0 at 414 nm in air saturated CH 2 Cl 2. Then, the photosensitizer was added to cuvette and photosensitizer s absorbance was adjusted to around Then, the cuvette was exposed to monochromatic light at the specific wavelength for 10 seconds depending on the efficiency of the triplet photosensitizers. The photosensitizer and MB were irradiated at the same wavelength. Absorbance was measured six times after each irradiation. Then, the slope of the curves of absorbance maxima of DPBF at 414 nm versus irradiation time for each photosensitizer were calculated. Singlet oxygen quantum yield (Φ Δ ) were calculated according to the equation (eqn (1)): ΦΔsam = ΦΔstd m m sam std F F std sam (eqn 1) where sam and std designate the Pt(II) photosensitizers and MB, respectively. m is the slope of difference in change in absorbance of DPBF (at 414 nm) with the irradiation time, F is the absorption correction factor, which is given by F = 1 10 D (D is the optical density, i.e. absorbance at the irradiation wavelength). S2

3 2.0 MR and HR MS spectra B F F 1 n-hexane Fig. S1 1 H MR of compound 1 (400 MHz, CDCl 3 ). ppm B F F ppm Fig. S2 1 H MR of compound 2 (400 MHz, CDCl 3 ). S3

4 B F F Pt Cl BDPY-Pt-1 Water n-hexane Fig. S3 1 H MR (400 MHz, CDCl 3 ) of complex BDPY-Pt-1. ppm B F F BDPY-Pt-1 Pt Cl ppm Fig. S4 13 C MR (100 MHz, CDCl 3 ) of BDPY-Pt-1. S4

5 JHR(CHCA) (1.749) TF LD e4 % B F F Pt Cl BDPY-Pt m/z Fig. S5 MALDI-HRMS of BDPY-Pt F F B Pt Cl BDPY-Pt Fig. S6 1 H MR (400 MHz, CDCl 3 ) of complex BDPY-Pt-2. ppm S5

6 F F B Pt Cl BDPY-Pt Fig. S7 13 C MR (100 MHz, CDCl 3 ) of BDPY-Pt ppm PM-1(CHCA) (3.585) TF LD e (M+) F F B Pt Cl % BDPY-Pt m/z Fig. S8 MALDI-HRMS of BDPY-Pt-2. S6

7 RH ppm Fig. S9 1 H MR (500 MHz, CDCl 3 ) of RH. S7

8 RH ppm Fig. S10 13 C MR (125 MHz, CDCl 3 ) of RH. Majumdar (0.371) AM (Cen,2, 80.00, Ht,5000.0,0.00,1.00); Sm (SG, 2x3.00); Cm (17:20) e3 % RH m/z Fig. S11 TF ES+ HRMS of RH. S8

9 RH-Pt Pt Cl n-hexane Water EtAc Fig. S12 1 H MR (500 MHz, CDCl 3 ) of RH-Pt ppm RH-Pt Pt Cl Fig. S13 13 C MR (125 MHz, CDCl 3 ) of RH-Pt. ppm S9

10 PM-1(CHCA) (0.901) TF LD % RH-Pt Pt Cl m/z Fig. S14 MALDI-HRMS of RH-Pt. Pt B F F RH-BDPY-Pt ppm Fig. S15 1 H MR (500 MHz, CDCl 3 ) of RH-BDPY-Pt-1. S10

11 Pt B F F RH-BDPY-Pt pp 95 Pt B F F RH-BDPY-Pt ppm Fig. S16 13 C MR (125 MHz, CDCl 3 ) of RH-BDPY-Pt-1. S11

12 PM-2(CHCA) (1.400) TF LD Pt P(n-Bu) B F F RH-BDPY-Pt m/z % Fig. S17 MALDI-HRMS of RH-BDPY-Pt-1. Pt B F F RH-BDPY-Pt ppm Fig. S18 1 H MR (500 MHz, CDCl 3 ) of RH-BDPY-Pt-2. S12

13 Pt B F F RH-BDPY-Pt pp 95 Pt B F F RH-BDPY-Pt ppm Fig. S19 13 C MR (125 MHz, CDCl 3 ) of RH-BDPY-Pt-2. S13

14 PM(CHCA) (0.834) TF LD e F F B % (n-bu) 3 P m/z Pt RH-BDPY-Pt-2 Fig. S20 MALDI-HRMS of RH-BDPY-Pt UV-Vis absorption spectra of the complex in different solvents Absorbance Toluene DCM MeC MeH a Absorbance Toluene DCM MeC MeH b Wavelength / nm Absorbance Toluene DCM MeC MeH c Absorbance Wavelength / nm Toluene DCM MeC MeH d Wavelength / nm Wavelength / nm Fig. S21 Solvent-polarity-dependence of the absorption of the complexes (a) BDPY-Pt-1, (b) RH- BDPY-Pt-1, (c) BDPY-Pt-2, (d) RH-BDPY-Pt-2. c = M. 20 C. S14

15 4.0 Emission Spectra, decay curve and Cyclic voltammogram of the complexes RH-BDPY-Pt-1 RH-Pt+TFA RH-BDPY-Pt-1+TFA Intensity Wavelength / nm Fig. S22 Emission of complexes. (a) RH-BDPY-Pt-1 (c = M), RH-Pt (c = M) + TFA (333 eqv.) and RH-BDPY-Pt-1(c = M) +TFA(333 eqv.) (λ ex = 550 nm). in deaerated dichloromethane. 20 C Δ.D τ T = 45.3 μs Time / μs Fig. S23 The decay curve of complexes BDPY-Pt-1+TFA (333 eqv.) at 580 nm (upon λ ex = 532 nm pulsed laser excitation). c = M in deaerated dichloromethane at 20 C. S15

16 Fc + /Fc Current Current a Fc + /Fc Potential / V Potential / V Fig. S24 Cyclic voltammogram of (a) RH-Pt in deaerated CH 2 Cl 2 solutions containing 1.0 mm photosensitizers with the ferrocene(fc) as internal reference, 0.10 M Bu 4 PF 6 as supporting electrode, Ag/Ag 3 as reference electrode. Scan rates: 0.1 mv/s. 5.0 DFT Calculations HM-2 HM-1 HM LUM LUM+1 LUM+2 Fig. S25 Electron density maps of the frontier molecular orbitals of complex BDPY-Pt-1 based on the optimized ground state geometry. The solvent toluene was considered in the calculations (PCM model). Calculated at the B3LYP/GECP/LAL2DZ level with Gaussian 09W. S16

17 Table S1: Excitation Energies (ev) and corresponding scillator Strengths (f), main configurations and CI coefficients of the Low-lying Electronically Excited States of complex BDPY-Pt-1, Calculated by TDDFT//B3LYP/LAL2DZ, based on the DFT//B3LYP/LAL2DZ ptimized Ground State Geometries Singlet TDDFT//B3LYP/LAL2DZ Electronic Energy f b Composition c CI d Character transition [ev/nm] a S 0 S / H L MLCT S 0 S / H 2 L MLCT Triplet S 0 T / H L MLCT a nly the selected low-lying excited states are presented. b scillator strengths. c nly the main configurations are presented. d The CI coefficients are in absolute values. e o spin-orbital coupling effect was considered, thus the f values are zero. HM-2 HM-1 HM LUM LUM+1 LUM+2 Fig. S26 Electron density maps of the frontier molecular orbitals of complex BDPY-Pt-2 based on the optimized ground state geometry. The solvent toluene was considered in the calculations (PCM model). Calculated at the B3LYP/GECP/LAL2DZ level with Gaussian 09W. S17

18 Table S2. Excitation Energies (ev) and corresponding scillator Strengths (f), main configurations and CI coefficients of the Low-lying Electronically Excited States of complex BDPY-Pt-2, Calculated by TDDFT//B3LYP/LAL2DZ, based on the DFT//B3LYP/LAL2DZ ptimized Ground State Geometries TDDFT//B3LYP/ LAL2DZ Electronic Energy f b Composition c CI d Character transition [ev/nm] a Singlet S 0 S / H L MLCT S 0 S / H 1 L ILCT S 0 S / H L ILCT Triplet S 0 T / H L MLCT a nly the selected low-lying excited states are presented. b scillator strengths. c nly the main configurations are presented. d The CI coefficients are in absolute values. e o spin-orbital coupling effect was considered, thus the f values are zero. S18

19 HM HM 2 HM 4 LUM+1 HM 1 HM 3 LUM LUM+2 Fig. S27 Electron density maps of the frontier molecular orbital of the complex RH-BDPY-Pt-1 in dichloromethane. Based on ground state optimized geometry by the DFT calculations at the B3LYP/GEECP level with Gaussian 09W. S19

20 Table S3. Electronic excitation energies (ev) and corresponding oscillator strengths (f), main configurations and CI coefficients of the low-lying electronic excited states of the complex RH- BDPY-Pt-1 in dichloromethane calculated by TDDFT//B3LYP/GEECP based on the DFT//B3LYP/ GEECP optimized ground state geometries Singlet Triplet Electronic transition Energy [ev/nm] a TDDFT//B3LYP/ GEECP f b Composition c CI d Character S 0 S / H L MLCT/ILCT S 0 S / H 4 L MLCT/ILCT H L MLCT/ILCT S 0 S / H 1 L ILCT H L LLCT S 0 S / H 1 L MLCT H 2 L MLCT H 3 L MLCT S 0 T / H L MLCT/ILCT S 0 T / H 4 L MLCT/ILCT S 0 T / H 1 L LLCT S 0 T / H 2 L LLCT S 0 T / H 3 L MLCT a nly the selected low-lying excited states are presented. b scillator strengths. c nly the main configurations are presented. d The CI coefficients are in absolute values. e o spin-orbital coupling effect was considered, thus the f values are zero. S20

21 HM HM 2 HM 3 HM 6 LUM LUM+1 Fig. S28 Electron density maps of the frontier molecular orbital of the complex RH(o)-BDPY-Pt-1 in dichloromethane. Based on ground state optimized geometry by the DFT calculations at the B3LYP/GEECP level with Gaussian 09W. S21

22 Table S4. Electronic excitation energies (ev) and corresponding oscillator strengths (f), main configurations and CI coefficients of the low-lying electronic excited states of the complex RH(o)-BDPY-Pt-1 in dichloromethane calculated by TDDFT//B3LYP/GEECP based on the DFT//B3LYP/ GEECP optimized ground state geometries. Singlet Triplet TDDFT//B3LYP/ GEECP Electronic Energy f b Composition c CI d Character transition [ev/nm] a S 0 S / H L LLCT S 0 S / H L ILCT H 3 L MLCT/ILCT S 0 S / H 2 L ILCT S 0 S / H 3 L MLCT/ILCT H L ILCT S 0 S / H 6 L ILCT S 0 T / H L ILCT 0 H 3 L MLCT/ILCT S 0 T / H 2 L ILCT 0 S 0 T / H L LLCT 0 S 0 T / H 3 L MLCT/ILCT 0 S 0 T / H 2 L ILCT 0 a nly the selected low-lying excited states are presented. b scillator strengths. c nly the main configurations are presented. d The CI coefficients are in absolute values. e o spin-orbital coupling effect was considered, thus the f values are zero. S22

23 Table S5. Electronic excitation energies (ev) and corresponding oscillator strengths (f ), main configurations and CI coefficients of the low-lying electronic excited states of the complex RH- Pt in dichloromethane calculated by TDDFT//B3LYP/GEECP based on the DFT//B3LYP/ GEECP optimized ground state geometries. TDDFT//B3LYP/ GEECP Electronic Energy f b Composition c CI d Character transition [ev/nm] a Singlet S 0 S / H L ILCT S 0 S / H 3 L ILCT S 0 S / H 7 L MLCT S 0 S / H L LLCT Triplet S 0 T / H L ILCT S 0 T / H 3 L ILCT S 0 T / H 1 L MLCT S 0 T / H 1 L MLCT a nly the selected low-lying excited states are presented. b scillator strengths. c nly the main configurations are presented. d The CI coefficients are in absolute values. e o spin-orbital coupling effect was considered, thus the f values are zero. S23

24 HM HM 1 HM 3 HM 7 LUM LUM+1 Fig. S29 Electron density maps of the frontier molecular orbital of the complex RH(o)-Pt in dichloromethane Based on ground state optimized geometry by the DFT calculations at the B3LYP/GEECP level with Gaussian 09W. S24

25 6.0 The x -y- z coordinates of the optimized geometries of complexes BDPY-Pt-1 ground state configuration (B3LYP/6-31G/LAL2DZ) Symbolic Z-matrix: Charge = 0 Multiplicity = 1 C P C H H H C H H H C H H H P C H H H C H H H C H H H C C C C C C C C C B F S25

26 F C H H H C H H H C H H H C H H H C C C C C H H H C H H Cl Pt C H BDPY-Pt-2 ground state configuration (B3LYP/6-31G/LAL2DZ) Symbolic Z-matrix: Charge = 0 Multiplicity = 1 C Pt P C H H H C H H S26

27 H C H H H P C H H H C H H H C H H H C C C C C C C C B F F C H H H C H H H C H H H C H H H S27

28 C C C C C H H H C H Cl C H C H RH-BDPY-Pt-1 ground state configuration (B3LYP/6-31G/LAL2DZ) Symbolic Z-matrix: Charge = 0 Multiplicity = 1 C P C H H H C H H H C H H H P C H H H C H H H C H S28

29 H H C C C C C C C C C B F F C H H H C H H H C H H H C H H H C C C C C H H H C H H C H C C S29

30 C C C C H H H C C C C C C C H H H C C C C C C H H H H C H H C C H C H C H C H C H H S30

31 C H H H C H H H C H H H H H C H H H C Pt RH-BDPY-Pt-2 ground state configuration (B3LYP/6-31G/LAL2DZ) Symbolic Z-matrix: Charge = 0 Multiplicity = 1 C C C C C C C B F F C H H H C H H H C S31

32 H H H C H H H C C C C C H H H H C H C C C H P C H H H C H H H C H H H P C H H H C H H H C H H S32

33 H C C C C C C H H H C C C C C C C H H H C C C C C C H H H H C H H C C H C H C H C H C S33

34 H H C H H H C H H H C H H H H H C H H H C Pt C RH-BDPY-Pt-1(open amide form) ground state configuration (B3LYP/6-31G/LAL2DZ) Symbolic Z-matrix: Charge = 1 Multiplicity = 1 C P C H H H C H H H C H H H P C S34

35 H H H C H H H C H H H C C C C C C C C C B F F C H H H C H H H C H H H C H H H C C C C C H S35

36 H H C H H C H C C Pt C C C C C C H H H C C C C C C H H H C H C H C H C H C C C C C C H H S36

37 H C H C H H H C H H H C H H H C H H H C H H H H H C H H RH-BDPY-Pt-2(open amide form) ground state configuration (B3LYP/6-31G/LAL2DZ) Symbolic Z-matrix: Charge = 1 Multiplicity = 1 C C C C C C C S37

38 B F F C H H H C H H H C H H H C H H H C C C C C H H H H C H C P C H H H C H H H C H H H P C H S38

39 H H C H H H C H H H C C C Pt C C H C C C C C C H H H C C C C C C H H H C H C H C H C H C S39

40 C C C C C H H H C H C H H H C H H H C H H H C H H H C H H H H H C H H RH- Pt(open amide form) ground state configuration (B3LYP/6-31G/LAL2DZ) Symbolic Z-matrix: Charge = 1 Multiplicity = 1 P C H H H S40

41 C H H H C H H H P C H H H C H H H C H H H C C Pt C C C C C C H H H C C C C C C H H H C H C H S41

42 C H C H C C C C C C H H H C H C H H H C H H H C H H H C H H H C H H H H H C H H Cl S42

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