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1 Electronic Supplementary Information A Sensitive Phosphorescent Thiol Chemosensor Based on an Iridium(III) Complex with α,β-unsaturated Ketone Functionalized 2,2 -Bipyridyl Ligand Na Zhao, a Yu-Hui Wu, a Lin-Xi Shi, a Qi-Pu Lin, a and Zhong-Ning Chen *,a,b State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian , China, and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai , China S1
2 Table S1. Partial Molecular Orbital Compositions (%) of 1 in DMF media under the TD-DFT Calculations. Orbital Energy (ev) MO contribution (%) Ir L ligand ppy 2,2 -bpy -C(O)C 6 H 4 N(C 2 H 5 ) 2 LUMO LUMO LUMO LUMO HOMO HOMO HOMO Table S2. TD-DFT Calculated Singlet Absorption Data and the Measured Absorption Data for 1 in DMF Media. Transition CI Coef. E, nm (ev) O.S. Assignment Measured value (nm) S1 HOMO 1 LUMO (2.42) MLCT / 1 LLCT S2 HOMO LUMO (2.61) ILCT 430,460 S6 HOMO LUMO (3.27) ILCT S31 HOMO LUMO (4.31) ILCT / 1 LLCT 298, 270 HOMO 6 LUMO MLCT/ 1 LLCT HOMO LUMO ILCT/ 1 LLCT S2
3 Table S3. Partial Molecular Orbital Compositions(%) of 1-Cys in DMF solution under the TD-DFT Calculations. Orbital Energy (ev) MO contribution (%) Ir L ligand ppy 2,2 -bpy -C(O)C 6 H 4 N(C 2 H 5 ) 2 LUMO LUMO LUMO HOMO HOMO HOMO Table S4. TD-DFT Calculated Singlet Absorption Data in DMF Media and the Measured Absorption Data for the adduct 1-Cys in DMF media. Transition CI Coef. E, nm (ev) O.S. Assignment Measured value (nm) S1 HOMO 1 LUMO (2.68) MLCT / 1 LLCT 416 S2 HOMO LUMO (3.08) ILCT S6 HOMO 2 LUMO (3.44) LLCT/ 1 MLCT 348 HOMO 1 LUMO MLCT / 1 ILCT S18 HOMO LUMO (4.02) ILCT 312,280 S3
4 Table S5 DFT Optimized Coordinates for 1-Cys Center Atomic Coordinates (Angstroms) Number Number X Y Z S4
5 S5
6 S6
7 S7
8 1.2 Absorbance L ligand Wavelength (nm) Fig. S1. UV vis absorption spectra of complex 1 and L ligand (20 μm) in DMF HEPES buffer solution (50 mm, ph 7.2, 4:1, v/v). 1.0 Absorbance Wavelength (nm) Fig. S2. Changes of UV vis absorption spectra for complex 1 (20 μm) in DMF HEPES buffer (50 mm, ph 7.2, 4:1, v/v) upon titration with Hcy (0 80 equiv). The equilibration time is about 300 min. S8
9 0.6 Absorbance Wavelength (nm) Fig. S3. Changes of UV vis absorption spectra for the ligand L (20 μm) in DMF HEPES buffer (50 mm, ph 7.2, 4:1, v/v) upon titration with Cys (0 60 equiv). 600 Emission Intensity Wavelength (nm) Fig. S4. Changes of emission spectra for complex 1 (20 μm) in DMF HEPES buffer (50 mm, ph 7.2, 4:1, v/v) upon titration with Hys (0 80 equiv). The equilibration time is about 300 min. S9
10 Emission Intensity Y = * X R = Concentration(10 5 M) Fig. S5. Plot of Hcy concentration dependence of the emission intensity at 587 nm. Emission Intensity Cys Hcy GSH t (min) Fig. S6. Time course of the emission intensity at 587 nm for complex 1 (20 μm) upon addition of 80 equiv of Cys, Hcy, or GSH in 300 min (25 o C). S10
11 Fig. S7. Positive ion ESI spectra of 1 before (a) and after (b) addition of 80 equiv Cys. H a O N HOOC NH 2 S O N H a' Cys H d N N N N H a H a H d Fig. S8. 1 H NMR spectra of free L before (a) and after (b) addition of 5 equiv Cys in d 6 -DMSO. S11
12 Fig. S9. The 1 H 1 H COSY spectrum of complex 1 in d 6 -DMSO. Fig. S10. The 1 H 1 H COSY spectrum of complex 2 in d 6 -DMSO. S12
13 Fig. S11. The 1 H 1 H COSY spectrum of complex 1 and 5 equiv in d 6 -DMSO H 2 O. 800 Emission Intensity Gly Ala Thr Ser Val Leu Ile Trp Phe Met Pro Gln Lys Asn Asp Glu His Arg Tyr Fig. S12. Emission response of complex 1 (20 μm) in the presence of both Cys and another competing amino acid (both 80 equiv) in DMF HEPES buffer solution (50 mm, ph 7.2, 4:1, v/v). The excitation wavelength was 358 nm. S13
14 1000 Emission Intensity Cys(80 equiv) ph Fig. S13. The emission intensities at 587 nm for 1 (20 μm) in the absence ( ) or presence ( ) of Cys (80 equiv) at various ph values. The excitation wavelength is 358 nm. Absorbance CH 3 CN CH 2 Cl 2 DMF Wavelength (nm) Fig. S14. UV vis absorption spectra of complex 1 (20 μm) in CH 3 CN (black), CH 2 Cl 2 (red) and DMF (blue) solutions. S14
15 Fig. S15. Optimized structures of 1 (top) and 1-Cys (bottom) in the ground state by DFT method. S15
16 Absorbance Oscillator Strength Wavelength (nm) Fig. S16. Calculated (red bars) absorption and experimentally measured (blue line) UV vis spectrum (20 μm) of 1 in DMF solution at ambient temperature. Absorbance Oscillator Strength Wavelength (nm) Fig. S17. Calculated (red bars) absorptions in DMF media and experimentally measured (blue line) UV vis spectrum (20 μm) of the adduct 1-Cys in DMF HEPES buffer solution (50 mm, ph 7.2, 4:1, v/v). S16
17 LUMO+6 LUMO+5 LUMO+1 LUMO HOMO HOMO 1 HOMO 6 Fig. S18. Electron-density diagrams of the frontier molecular orbitals involved in absorption of 1 in DMF media. S17
18 LUMO+4 LUMO+3 LUMO HOMO HOMO 1 HOMO 2 Fig. S19. Electron-density diagrams of the frontier molecular orbitals involved in absorption of 1-Cys in DMF media. S18
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