Supporting Information for Rapid and Highly Sensitive Dual-Channel Detection of Cyanide by Bis-heteroleptic Ruthenium(II) Complexes
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1 Supporting Information for Rapid and Highly Sensitive Dual-Channel Detection of Cyanide by Bis-heteroleptic Ruthenium(II) Complexes Snehadrinarayan Khatua, Debabrata Samanta, Jan W. Bats, Michael Schmittel * Center of Micro and Nanochemistry and Engineering, Organische Chemie I, Universität Siegen, Adolf-Reichwein-Str. 2, D Siegen, Germany, Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität, Max-von-Laue Strasse 7, D Frankfurt am Main, Germany schmittel@chemie.uni-siegen.de Fax: (+49) Table of Contents 1 List of Compounds. S2 2 NMR spectra of PDA S2 3 ESI mass spectrum of PDA S3 4 NMR spectra of 1[PF 6 ] 2 and 2[PF 6 ] 2 S4 5 ESI mass spectra of 1[PF 6 ] 2 and 2[PF 6 ] 2 S9 6 Cyclic voltammetric (CV) analysis S10 7 UV-vis data of 2[PF 6 ] 2 S12 8 UV-vis data of 1[PF 6 ] 2 S13 9 Photoluminescence data of 1[PF 6 ] 2 S14 10 Calculation of detection limit S15 11 ESI mass spectrum of 2[PF 6 ] 2 with CN - S15 12 PL titration of 2[PF 6 ] 2 in aqueous acetonitrile and the time course S16 13 Calculated molecular orbitals S17 14 Table for main optical transitions S18 15 Energy minimized structure of the 1-(CN) 2, and 2-(CN) 2 S19 16 Coordinates from the computation S20 17 References S22 S1
2 Chart S1. List of compounds CHO CHO 9 7 CHO N 7 N 11 2 N N 14 N 5 N 14 N Ru II 11 6 Ru II N N N N 12 N N CHO N 2 4 CHO 2 4 CHO PDA 1 2 Figure S1. 1 H NMR spectrum of the ligand, PDA in CDCl 3. S2
3 Figure S2. 13 C NMR spectrum of the ligand PDA in CDCl 3. Figure S3. ESI mass spectrum of the ligand PDA in CHCl 3. S3
4 Figure S4. 1 H NMR of compound 1[PF 6 ] 2 in acetone d 6. Figure S5. 1 H- 1 H COSY NMR spectrum of compound 1[PF 6 ] 2 in acetone d 6. S4
5 Figure S6. 13 C NMR spectrum of compound 1[PF 6 ] 2 in acetone d 6. Figure S7. 1 H- 13 C HSQC NMR spectrum of compound 1[PF 6 ] 2 in acetone d 6. S5
6 Figure S8. 1 H- 13 C HMBC NMR spectrum of compound 1[PF 6 ] 2 in acetone d 6. Figure S9. 1 H NMR spectrum of compound 2[PF 6 ] 2 in acetone d 6. S6
7 Figure S10. 1 H- 1 H COSY NMR spectrum of compound 2[PF 6 ] 2 in acetone d 6. Figure S C NMR spectrum of compound 2[PF 6 ] 2 in acetone d 6. S7
8 Figure S12. 1 H- 13 C HSQC NMR spectrum of compound 2[PF 6 ] 2 in acetone d 6. Figure S13. 1 H- 13 C HMBC NMR spectrum of compound 2[PF 6 ] 2 in acetone d 6. S8
9 Figure S14. ESI mass spectrum of compound 1[PF 6 ] 2 in CH 3 CN. Figure S15. ESI mass spectrum of compound 2[PF 6 ] 2 in CH 3 CN. S9
10 (a) (b) Figure S16a. Cyclic voltammetric (CV) analysis of a 1 mm solution of 1[PF 6 ] 2 in actonitrile versus the FeCp 2 0/+ couple. (a) Oxidation of 1[PF 6 ] 2 ; (b) reduction of 1[PF 6 ] 2. S10
11 (c) (d) Figure S16b. Cyclic voltammetric (CV) analysis of a 1 mm solution of 2[PF 6 ] 2 in actonitrile versus the FeCp 2 0/+ couple. (c) Oxidation of 2[PF 6 ] 2 ; (d) reduction of 2[PF 6 ] 2. S11
12 (a) (b) Figure S17. (a) Expanded UV-vis titration spectrum of 2[PF 6 ] 2 (20 µm) with CN solution (0-2.0 equiv.) in CH 3 CN at 25 C. (b) The spectra of the 1:1 and 1:2 adduct of 2[PF 6 ] 2 with CN as derived from the titration. S12
13 (a) (b) Figure S18. (a) UV-vis titration of 1[PF 6 ] 2 (20 µm) with CN solution ( equiv.) in CH 3 CN at 25 C. (b) Plot of the change of ratio of absorbance at 232 nm and 261 nm upon addition of CN solution (the linearization serves to illustrate the change in stoichiometry). S13
![(a) (b) Figure S19. (a) PL titration of 1[PF 6 ] 2 (20 µm) with a CN solution (0-2.0 equiv.) in CH 3 CN at 25 C.](/docs-images/86/93187218/images/14-1.jpg "(b) Plot of the PL intensity change at 624 nm upon addition of the CN solution (the linearization serves to illustrate the change in")
14 (a) (b) Figure S19. (a) PL titration of 1[PF 6 ] 2 (20 µm) with a CN solution (0-2.0 equiv.) in CH 3 CN at 25 C. (b) Plot of the PL intensity change at 624 nm upon addition of the CN solution (the linearization serves to illustrate the change in stoichiometry). S14
15 Figure S20. A calibration curve for CN over the concentration range between 0 and 19.6 µm derived from the PL titration with 2[PF 6 ] 2 (20.0 µm). The detection limit was calculated according to the equation DL = 3 SD/slope. 1 SD corresponds to the standard deviation of the blank sample (obtained by 10 consecutive scans of the blank sample). Figure S21. ESI mass spectrum of compound 2[PF 6 ] 2 after addition of a slight excess of tetra-n-butylammonium cyanide (TBACN) in CH 3 CN. S15
![2[PF 6 ] 2 upon addition of 2.0 equiv.](/docs-images/86/93187218/images/16-9.jpg "of cyanide in CH 3 CN and in 1%, 3% and 5 %")
16 (a) (b) (c) (d) Figure S22. PL titration of 2[PF 6 ] 2 with CN in (a) 1%, (b) 3% and (c) 5 % aqueous acetonitrile. (d) The time course of the PL response of 2[PF 6 ] 2 upon addition of 2.0 equiv. of cyanide in CH 3 CN and in 1%, 3% and 5 % aqueous acetonitrile at 25 C. S16
17 Figure S23. Calculated MOs of 1, 1-(CN) 2, 2 and 2-(CN) 2 [isovalue = 0.05]. S17
18 Table S1. Main calculated optical transitions for 1, 1-(CN) 2, 2 and 2-(CN) 2. Compounds 1 Computed vertical excitation energy (ev) 2.81 Experimentally observed transition energy (ev) 2.63 Transition HOMO - 1 LUMO + 1 Oscillator strength (f) HOMO - 2 LUMO (CN) HOMO - 1 LUMO HOMO - 2 LUMO HOMO - 2 LUMO HOMO - 2 LUMO HOMO - 2 LUMO (CN) HOMO - 1 LUMO HOMO - 2 LUMO HOMO - 1 LUMO HOMO - 2 LUMO S18
19 (a) (b) Figure S24. Energy minimized structure of (a) 1-(CN) 2, and (b) 2-(CN) 2. S19
20 Table S2: The x,y,z cartesian coordinates of the corresponding compounds calculated using Gaussian03 at B3LYP/6-31G (d) level and LANL2DZ for Ru. 1 Ru N N N N N N C C C C C C C C C C C C C C C C C 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 H H H H H H H H H H H H O O (CN) 2 Ru N N N N N N N N C C C C C C C C C C C C C C C C S20 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
21 C C C C C C C C C C C C H H H H H H H H H O O Ru N N N N N N C C C C C C C C C C C C C C C C C C C C C 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 H H H H H H H H H H H H O O S21
22 2-(CN) 2 Ru N N N N N N N N C C C C C C C C C C C C C C C C C C C C C C C 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 H H H H H H H H H H H H H H O O References 1. (a) Niu, H.-T.; Su, D.; Jiang, X.; Yang, W.; Yin, Z.; He, J.; Cheng J. -P., Org. Biomol. Chem., 2008, 6, (b) Zhu, M. Yuan, M. Liu, X. Xu, J. Lv, J. Huang, C. Liu, H. Li, Y. Wang, S. Zhu, D., Org. Lett., 2008, 10, # End # S22
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