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1 DOI: /NCHEM.2201 Highly emissive platinum(ii) metallacages Xuzhou Yan, 1 Timothy R. Cook, 2 Pi Wang, 1 Feihe Huang,,1 and Peter J. Stang,3 1 Center for Chemistry of High-Performance & Novel Materials, State Key Laboratory of Chemical Engineering, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang , P. R. China 2 Department of Chemistry, University at Buffalo, 359 Natural Sciences Complex, Buffalo, New York, Department of Chemistry, University of Utah, 315 South 1400 East, Room 2020, Salt Lake City, Utah addresses: fhuang@zju.edu.cn; stang@chem.utah.edu Table of Contents S1. Materials and methods 2 S2. Synthesis of tetragonal metallacage 1 3 S3. Synthesis of PEG-functionalized tetragonal metallacage 2 5 S4. 2D DOSY NMR spectra of metallacages 1 and 2 7 S5. DLS data of metallacages 1 and 2 in CH 2 Cl 2 8 S6. Fluorescence emission spectra of S7. Absorption spectra of metallacages 1 and 2 in CH 2 Cl 2 /hexane mixtures with different hexane contents 9 S8. Quantum yields of metallacages 1 and 2 in CH 2 Cl 2 /hexane mixtures with different hexane contents 9 S9. DLS data of metallacages 1 and 2 in CH 2 Cl 2 /hexane mixtures 10 S10. TEM images of polymeric metallacage 1 in CH 2 Cl 2 /hexane solutions with different hexane contents 10 S11. TEM images of polymeric metallacage 2 in CH 2 Cl 2 /hexane solutions with different hexane contents 11 S12. Absorption spectra of metallacages 1 and 2 in different solvents 11 S13. Quantum yields of metallacages 1 and 2 in different solvents 12 S14. Temperature dependence of fluorescence emission spectra of metallacage 1 and 2 in different solvents 12 S15. Fluorescence emission spectra and photographs (inset) of polymeric metallacage 2 in THF with different times 13 S16. Absorption spectra of Polymeric Metallacage 2 in different ester solvents 14 S17. TEM images of polymeric metallacage 2 in different ester compounds 14 S18. Illustration of the molecular structure of the aggregates 15 S19. Solubility data of the two metallacages 16 NATURE CHEMISTRY 1
2 S1. Materials and methods All reagents were commercially available and used as supplied without further purification. Deuterated solvents were purchased from Cambridge Isotope Laboratory (Andover, MA). Compounds 3 S1, 5 S2, and 6 S3 were prepared according to the published procedures. 1 H and 31 P{ 1 H} NMR spectra were recorded with a Bruker Avance DMX 500 spectrophotometer or a Bruker Avance DMX 400 spectrophotometer with use of the deuterated solvent as the lock and the residual solvent or TMS as the internal reference. 31 P{ 1 H} NMR chemical shifts are referenced to an external unlocked sample of 85% H 3 PO 4 (δ 0.0). 2D DOSY NMR spectra were recorded on a Varian Unity 600 MHz spectrometer. Mass spectra were recorded on a Micromass Quattro II triple-quadrupole mass spectrometer using electrospray ionization and analyzed with the MassLynx software suite. Dynamic light scattering (DLS) was carried out on a Malvern Nanosizer S instrument at room temperature. Transmission electron microscopy (TEM) investigations were carried out on a JEM-1200EX instrument. The fluorescence experiments were conducted on a RF-5301 spectrofluorophotometer (Shimadzu Corporation, Japan). The temperature-dependent fluorescent experiments were conducted on a Hitachi F-3000 fluorescence spectrophotometer. NATURE CHEMISTRY 2
3 S2. Synthesis of tetragonal metallacage 1 Tetra(4-pyridylphenyl)ethylene compound 3 (3.20 mg, 5.00 μmol), cis-pt(pet 3 ) 2 (OTf) 2 6 (14.6 mg, 20.0 μmol), and carboxylate ligand 4 (2.10 mg, 10.0 μmol) were placed in a 2-dram vial, followed by addition of H 2 O (0.200 ml) and acetone (0.800 ml). After 8 h of heating at 70 C, all solvent was removed by N 2 flow and the solid was dried under vacuum. Acetone (0.500 ml) was then added into the resultant mixture, and the solution was stirred for 30 min at room temperature. Then, the mixture was filtered to remove insoluble materials. The resulting tetragonal metallacage 1 was precipitated with diethyl ether, isolated and dried under reduced pressure and dissolved in CD 2 Cl 2 for characterization. The 1 H NMR spectrum of tetragonal metallacage 1 is shown in Figure S1. 1 H NMR (CD 2 Cl 2, room temperature, 500 MHz) δ (ppm): 8.58 (d, J = 5.0 Hz, 16H), 7.96 (t, J = 5.0 Hz, 4H), (m, 8H), 7.62 (d, J = 5.0 Hz, 16H), 7.40 (d, J = 10.0 Hz, 16H), 7.19 (t, J = 15.0 Hz, 4H), 7.10 (d, J = 10.0 Hz, 16H), (m, 96H), (m, 144H). The 31 P { 1 H} NMR spectrum of tetragonal metallacage 1 is shown in Figure S2. 31 P{ 1 H} NMR (CD 2 Cl 2, room temperature, MHz) δ (ppm): 5.27 (d, 2 J P P = 20.0 Hz, 195 Pt satellites, 2 J Pt P = 3210 Hz), and 0.54 (d, 2 J P P = 20.0 Hz, 195 Pt satellites, 2 J Pt P = 3526 Hz). TOF-ESI-MS is shown in Figure S3: m/z [M 6OTf] 6+, [M 4OTf + 2Na] 6+, [M 4OTf 1HOTf + K] 5+, [M 3OTf + Na] 5+, [M 4OTf] 4+. NATURE CHEMISTRY 3
4 Supplementary Figure S1 1 H NMR spectrum (CD 2 Cl 2, room temperature, 500 MHz) of tetragonal metallacage 1. Supplementary Figure S2 31 P{ 1 H} NMR spectrum (CD 2 Cl 2, room temperature, MHz) of tetragonal metallacage 1. NATURE CHEMISTRY 4
5 +ESI 全扫描 ( 分钟, 3 扫描数 ) Frag=125.0V XZY-126B-1.d 计数 (%) 与质荷比 (m/z) Supplementary Figure S3 Experimental (red) and calculated (blue) electrospray ionization mass spectra of metallacage 1. S3. Synthesis of PEG-functionalized tetragonal metallacage 2 Tetra(4-pyridylphenyl)ethylene compound 3 (2.56 mg, 4.00 μmol), cis-pt(pet 3 ) 2 (OTf) 2 6 (11.7 mg, 16.0 μmol), and PEG-functionalized carboxylate ligand 5 (7.21 mg, 8.00 μmol) were placed in a 2-dram vial, followed by addition of H 2 O (0.200 ml) and acetone (0.800 ml). After 8 h of heating at 70 C, all solvent was removed by N 2 flow and the solid was dried under vacuum. Acetone (0.500 ml) was then added into the resultant mixture, and the solution was stirred for 3 h at 70 C. Then, the mixture was filtered to remove insoluble materials. The resulting PEG-functionalized tetragonal metallacage 2 was precipitated with diethyl ether, isolated and dried under reduced pressure and dissolved in CD 2 Cl 2 for characterization. The 1 H NMR spectrum of tetragonal metallacage 2 is shown in Figure S4. 1 H NMR (CD 2 Cl 2, room temperature, 500 MHz) δ (ppm): 8.58 (d, J = 5.0 Hz, 16H), 7.62 (d, J = 5.0 Hz, 16H), 7.57 (s, 4H), 7.41 (d, J = 10.0 Hz, 16H), 7.38 (s, 8H), 7.10 (d, J = 10.0 Hz, 16H), (m, 252H), (m, 96H), (m, 144H). The 31 P { 1 H} NMR spectrum of tetragonal metallacage 2 is shown in Figure S5. 31 P{ 1 H} NMR (CD 2 Cl 2, room temperature, MHz) δ (ppm): 5.12 (d, 2 J P P = 22.0 Hz, 195 Pt satellites, 2 J Pt P = 3225 Hz), and 0.60 (d, 2 J P P = 22.0 Hz, 195 Pt satellites, 2 J Pt P = 3441 Hz). TOF-ESI-MS is shown in Figure NATURE CHEMISTRY 5
6 S6: m/z [M 4OTf HOTf + 2Na + 2K] 8+, [M 4OTf + 4K] 8+, [M 4OTf 3HOTf + 3K] 7+, [M 4OTf 2HOTf + 3K] 7+, [M 4OTf + 3K] 7+. Supplementary Figure S4 1 H NMR spectrum (CD 2 Cl 2, room temperature, 500 MHz) of tetragonal metallacage 2. NATURE CHEMISTRY 6
7 Supplementary Figure S5 31 P{ 1 H} NMR spectrum (CD 2 Cl 2, room temperature, MHz) of tetragonal metallacage Supplementary Figure S6 Experimental (red) and calculated (blue) electrospray ionization mass spectra of metallacage 2. NATURE CHEMISTRY 7
8 S4. 2D DOSY NMR spectra of metallacages 1 and 2 Supplementary Figure S7 2D DOSY NMR spectra (CD 2 Cl 2, room temperature, 600 MHz) of metallacages 1 (a) and 2 (b) at 5.00 mm. S5. DLS data of metallacages 1 and 2 in CH 2 Cl Metallacage 1 Metallacage 2 50 Number / % Size / nm Supplementary Figure S8 Size distributions of metallacages 1 and 2 at 1.00 mm in CH 2 Cl 2. NATURE CHEMISTRY 8
9 S6. Fluorescence emission spectra of 1 3 Supplementary Figure S9 Fluorescence emission spectra of TPPE ligand 3 and metallacages 1 and 2 in CH 2 Cl 2 (λ ex = 355 nm, c = 10.0 μm). Inset: Photograph of ligand 3 and metallacages 1 and 2 in CH 2 Cl 2 excited at 365 nm using a UV lamp at 298 K. S7. Absorption spectra of metallacages 1 and 2 in CH 2 Cl 2 /hexane mixtures with different hexane contents Supplementary Figure S10 Absorption spectra of metallacages 1 (a) and 2 (b) in CH 2 Cl 2 /hexane mixtures with different hexane contents (c = 10.0 μm). NATURE CHEMISTRY 9
10 S8. Quantum yields of metallacages 1 and 2 in CH 2 Cl 2 /hexane mixtures with different hexane contents Supplementary Figure S11 Quantum yields of metallacages 1 (a) and 2 (b) in CH 2 Cl 2 /hexane mixtures with different hexane contents. Quantum yield was determined using quinine sulfate at 365 nm (Φ F = 56%). S9. DLS data of metallacages 1 and 2 in CH 2 Cl 2 /hexane mixtures Supplementary Figure S12 Size distributions of metallacages 1 (a) and 2 (b) in CH 2 Cl 2 /hexane mixtures. The percentages in the graphs are the hexane content. NATURE CHEMISTRY 10
11 S10. TEM images of metallacage 1 in CH 2 Cl 2 /hexane solutions with different hexane contents Supplementary Figure S13 TEM images of the aggregates of 1 formed in the CH 2 Cl 2 /hexane mixtures containing 40% (a and d), 60% (b and e), and 80% (c and f) hexane. S11. TEM images of polymeric metallacage 2 in CH 2 Cl 2 /hexane solutions with different hexane contents Supplementary Figure S14 TEM images of the aggregates of 2 formed in the CH 2 Cl 2 /hexane mixtures containing 40% (a and e), 60% (b and f), 70% (c and g), and 80% (d and h) hexane. NATURE CHEMISTRY 11
12 S12. Absorption spectra of metallacages 1 and 2 in different solvents Supplementary Figure S15 Absorption spectra of metallacages 1 (a) and 2 (b) in different solvents (c = 10.0 μm). S13. Quantum yields of metallacages 1 and 2 in different solvents Supplementary Figure S16 Quantum yields of metallacages 1 (a) and 2 (b) in different solvents. Quantum yield was determined using quinine sulfate at 365 nm (Φ F = 56%). The large absorption band at ~275 nm in water for cages 1 and 2 (SI, Fig. S15) does not populate an emissive excited state. As such, 330 nm was selected as the excitation wavelength for quantum yield measurements. Although the quantum yield in water is relatively high, the low absorption at longer wavelengths in this solvent makes solutions of the cages weakly emissive. NATURE CHEMISTRY 12
13 S14. Temperature dependence of fluorescence emission spectra of metallacage 1 and 2 in different solvents Supplementary Figure S17 Temperature dependence of fluorescence emission spectra of metallacage 1 in CH 2 Cl 2 (a), THF (b), EA (c), and dioxane (d). λ ex = 355 nm, c = 10.0 μm. Supplementary Figure S18 Temperature dependence of fluorescence emission spectra of metallacage 2 in CH 2 Cl 2 (a) and EA (b). c = 10.0 μm. NATURE CHEMISTRY 13
14 S15. Fluorescence emission spectra and photographs (inset) of polymeric metallacage 2 in THF with different times Supplementary Figure S19 Fluorescence emission spectra and photographs (inset) of 2 in THF with different times (λ ex = 355 nm, c = 10.0 μm). S16. Absorption spectra of Polymeric Metallacage 2 in different ester solvents Supplementary Figure S20 Absorption spectra of polymeric metallacage 2 in different ester solvents (c = 10.0 μm). NATURE CHEMISTRY 14
15 S17. TEM images of polymeric metallacage 2 in different ester compounds Supplementary Figure S21 TEM images of the aggregates of 2 formed in methyl formate (a and e), ethyl formate (b and f), ethyl acetate (c and g), and butyl acetate (d and h), respectively. S18. Illustration of the molecular structure of aggregate Supplementary Figure S22 Partial 1 H NMR spectra of PEG-functionalized metallacage 2 (CD 2 Cl 2, room temperature, 500 MHz): (a) 1.25 mm; (b) 2.50 mm; (c) 5.00 mm; (d) 10.0 mm; (e) 20.0 mm. NATURE CHEMISTRY 15
16 Supplementary Figure S23 Partial 1 H (a, b) and 31 P{ 1 H} (c, d) NMR spectra (CD 2 Cl 2, 293 K) of PEG-functionalized metallacage 2 before (a, c) and after (b, d) aggregation in CH 2 Cl 2 /hexane mixture solution (70% hexane content). The enhanced emission of the two assemblies in CH 2 Cl 2 /hexane mixture solutions originates from their aggregation through the stacking of TPE face between cages. In order to rule out the possibility of the formation of a polymer network through the flipping of a benzene dicarboxylate ligand during aggregation, we conducted 1 H NMR experiments to evidence the discrete nature of the assemblies before and after aggregation. For these experiments, we selected PEG-functionalized metallacage 2. As shown in Fig. S22, the 1 H NMR spectra of assembly 2 is virtually invariant to increases from its initial concentration ( mm), indicating that the assembly does not form a polymer (instead, aggregation occurs at higher concentration). Subsequently, we collected the aggregate from a 70% hexane content solution for 1 H and 31 P{ 1 H}NMR experiments. By comparing these spectra with those of the discrete metallacage, we found that the aggregate kept its original molecular structure (Fig. S23). S19. Solubility data of the two metallacages Unit: mm Temperature:20 C a CCl 4 Tol a THF EA BA a CH 2 Cl 2 CHCl 3 Dio a MeOH H 2 O Cage 1 < 10 3 < < < Cage 2 < 10 3 < < a Cyan emission is observed for solutions of the cages in solvents where they are sparingly soluble. Since the cages are so poorly soluble at typical concentrations for emission (10 3 mm) a qualitative upper limit of solubility is given for these solvents. Supplementary Table S1 Solubility data of the two metallacages were obtained by weighing a fixed amount of cage 1 or 2 in a 0.5 ml centrifuge tube and then adding appropriate solvent to make it just soluble. These solubility differences appear to be associated with different wavelengths of emissions observed in Fig. 3 in the main text. NATURE CHEMISTRY 16
17 References: S1. Wang, M., Zheng, Y.-R., Ghosh, K. & Stang, P. J. Metallosupramolecular tetragonal prisms via multicomponent coordination-driven template-free self-assembly. J. Am. Chem. Soc. 130, (2010). S2. Yan, X. et al. Hierarchical self-assembly: well-defined supramolecular nanostructures and metallohydrogels via amphiphilic discrete organoplatinum(ii) metallacycles. J. Am. Chem. Soc. 135, (2013). S3. Zheng, Y.-R. et al. A facile approach toward multicomponent supramolecular structures: selective self-assembly via charge separation. J. Am. Chem. Soc. 132, (2010). NATURE CHEMISTRY 17
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