The Design and Synthesis of 60 Dendritic Donor Ligands and Their. Coordination-Driven Self-Assembly into Supramolecular. Rhomboidal Metallodendrimers
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1 The Design and Synthesis of 60 Dendritic Donor Ligands and Their Coordination-Driven Self-ssembly into Supramolecular Rhomboidal Metallodendrimers Qing Han, Quan-Jie Li, Jiuming He &, ingjie Hu #, Hongwei Tan, Zeper bliz &, Cui-Hong Wang, Yihua Yu #, and Hai-o Yang, * Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai , P. R. China Department of Chemistry, eijing Normal University, eijing , P. R. China & Institute of Materia Medica, Chinese cademy of Medical Sciences and Peking Union Medical College, eijing , P. R. China #Shanghai Key Laboratory of Magnetic Resonance, Department of Physics, East China Normal University, Shanghai , P. R. China hbyang@chem.ecnu.edu.cn Table of Contents 1 H and 13 C NMR Spectra of Precursors 5a c and 1a c...2 High Resolution Mass Spectra of Precursors 5a c and 1a c...17 CIS-TF-MS Spectrum of [G-3] Rhomboidal Metallodendrimer R Cyclic Voltammetry Measurements of R7 R The 1 H DSY NMR Spectra of R7 R9 in CD 2 Cl The Model Structures of Rhomboidal metallodendrimers
2 1 H and 13 C NMR Spectra of Precursors 5a c and 1a c Figure S1. 1 H () and 13 C () NMR spectra of compound 5a in CDCl 3. 2
3 Figure S2. 1 H () and 13 C (C) NMR spectra of compound 5b in CDCl 3. 3
4 Figure S3. 1 H () and 13 C (C) NMR spectra of compound 5c in CDCl 3. 4
5 Figure S4. 1 H () and 13 C () NMR of compound 1a in CDCl 3. 5
6 Figure S5. 1 H () and 13 C () NMR spectra of compound 1b in CDCl 3. 6
7 Figure S6. 1 H () and 13 C () NMR spectra of compound 1c in CDCl 3. 7
8 Figure S7. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R1 in CD 2 Cl 2. 8
9 Figure S8. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R2 in CD 2 Cl 2. 9
10 Figure S9. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R3 in CD 2 Cl 2. 10
11 Figure S10. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R4 in CD 2 Cl 2 and acetone-d Et 3 P Pt Pt PEt 3 N N PEt 3 Et 3 P 4N 3 - PEt N 3 Pt Et 3 P Et 3 P N Pt PEt 3 11
12 Figure S11. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R5 in CD 2 Cl 2 and acetone-d 6. 12
13 Figure S12. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R6 in CD 2 Cl 2 and acetone-d Et 3P Pt Pt PEt 3 N N PEt 3 Et 3P PEt N 3 Pt Et 3P Et 3P Pt N PEt 3 4N 3-13
14 Figure S13. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R7 in CD 2 Cl 2. 14
15 Figure S14. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R8 in CD 2 Cl 2. 15
16 Figure S15. 1 H () and 31 P () NMR spectra of rhomboidal metallodendrimer R9 in CD 2 Cl 2. 16
17 High Resolution Mass Spectra of Precursors 5a c and 1a c Figure S16. HR MLDI-MS spectrum of 5a, m/z calced for C 28 H 20 r 2 2 Na, ([M+Na] + ): , found: Figure S17. HR MLDI-MS spectrum of 5b, m/z calced for C 56 H 44 r 2 6 Na ([M+Na] + ): , found:
18 Figure S18. HR MLDI-MS spectrum of 5c, m/z calced for C 112 H 92 r 2 14 Na ([M+Na] + ): , found: Figure S19. High resolution mass spectrum (EI + ) of 1a, m/z calced for C 42 H 28 N 2 2, (M + ) , found:
19 Figure S20. High resolution mass spectrum (ESI + ) of 1b, m/z calced for C 70 H 53 N 2 6, (M) + : , found Figure S21. HR MLDI-MS spectrum of 1c, m/z calced for C 126 H 100 N 2 14 Na ([M+Na] + ): , found:
20 CIS-TF-MS Spectrum of [G-3] Rhomboidal Metallodendrimer R6 Figure S22. Calculated (top) and experimental (bottom) CSI-TF-MS spectra of R6, m/z calced for C 530 H 504 N 4 60 P 8 Pt 4 ([M-4N 3 ] 4+ ): , found:
21 Cyclic Voltammetry Measurements of R7 R9 Cyclic voltammetry (CV) was performed using a 3-electrode cell and a RST electrochemical work station. The working electrode was a glassy carbon disk with surface area of about 7.0 mm 2. SCE electrode was used as reference electrode and a Pt wire as the counter electrode. The CV measurements were carried out in a dichloromethane solution containing 0.2 M tetra-n-butylammonium hexafluorophosphate (n-u 4 NPF 6 ). The concentration of redox molecule in solution was: (1) [G-1] rhomboid R7, M, (2) [G-2] rhomboid R8, M, (3) [G-3] rhomboid R9, M. The results of electrochemical studies are summarized in the Table 1 of the main text and shown in Figure S23. Scan rates are indicated in the figures. In reversible system, the peak current (i) with respect to the scanning speed (v) can be expressed as: i = n 3/2 F 3/2 (RT) -1/2 D 1/2 Cv 1/2. Where the F 3/2 (RT) -1/2 is a constant which has a value of ; n is the mole of electrons transferred per mole of electroactive species (in our system,n=1); is the area of the electrode in cm 2 ; D is the diffusion coefficient in cm 2 /s; C is the concentration of samples in mol/ml; and v is the scan rate of the potential in volt/s. plot of i vs v 1/2 should give a straight line, the slope of which can be used to determine the diffusion coefficient, if n,, and C are known. Thus by plotting i vs v 1/2, D can be evaluated from the slope. The results are outlined in Table1 of main text. The errors of slopes were estimated by fitting the data with two reasonable lines with a maximum slope and a minimum slope and taking one-half of the difference between the max and min slopes. 21
22 Figure S23. Cyclic voltammograms of R7 (1), R8 (2) and R9 (3) at a scan rate of mv/s and plot of the experimental ratio i vs v 1/2 at a scan rate of mv/s (1-3 for R7 R9)
23 The 1 H DSY NMR Spectrum of R7 R9 in CD 2 Cl 2 Figure S24. The 1 H DSY spectrum of R7 (), R8 () and R9 (), recorded at 292.5k, ruker 500MHz(CD 2 Cl 2 ). 16 gradient increments were acquired in 128 scans, with a diffusion time( ) of 120 ms and bipolar pulse field gradient total duration(δ) of 1.5 ms for a total of 2 h. () 23
24 () (C) 24
25 The Model Structures of Rhomboidal metallodendrimers Figure S25. The Model Structures of Rhomboidal Metallodendrimers R1 () and R2 (). 0.7 nm 2.9 nm 2.1 nm 1.2 nm 2.9 nm 2.1 nm Figure S26. The Model Structures of Rhomboidal Metallodendrimers R4 () and R5 (). 1.9 nm 1.3 nm 0.7 nm 2.7 nm 1.7 nm 1.3 nm 2.7 nm 1.7 nm 25
26 Figure S27. The Model Structures of Rhomboidal Metallodendrimers R7 () and R8 (). 0.7 nm 2.8 nm 1.6 nm 1.3 nm 2.8 nm 1.6 nm 26
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