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1 Supporting Information Selective Metal Cation Capture by Soft Anionic Metal-Organic Frameworks via Drastic Single-crystal-to-single-crystal Transformations Jian Tian, Laxmikant V. Saraf, Birgit Schwenzer, Stephanie M. Taylor, Euan K. Brechin, Jun Liu, Scott J. Dalgarno* and Praveen K. Thallapally* SI 1
2 Content General experimental details Figure S1: ORTEP drawing of 1a and 1b crystals and additional representations of crystal structures of 1a and 1b. Figure S2: Comparison of L 4- conformers in 1a and 1b. Figure S3: The coordination modes of L 4- linker in complexes 1a, 1b, 2, 3 and 1a-Cu. Figure S4: Crystallographic view along the b crystal axis of the 1a-Cu structure. Figure S5: Photometric spectra monitoring cation uptake. Figure S6: Plot of the χ M T versus T for complexes 1-3. Figure S7: ORTEP drawing of 2 and 3 and additional representations of crystal structures. Figure S8: Crystal pictures of 1a, 2, 1a-Cu, and 3 Figure S9: PXRD patterns of as-synthesized samples. Figure S10: TGA curves for complex 1a, 1b, 2 and 3. Figure S11: Selected EDX spectra of TM 2+ -captured complex of 1a Figure S12: Selected EDX spectra of 1a for selective capture of TM 2+ over alkali ions Table S1. Metal ion analysis for the products after capture/exchange of TM 2+ Table S2. Metal ion analysis for the products after selective metal cation capture/exchange Table S3. Crystallographic parameters for 1a, 1b, 1-Cu, 2 and 3 SI 2
3 Experimental details: Materials and Methods : Tetrakis[4-(carboxyphenyl)oxamethyl]methane acid (H 4 L) was synthesized according to published procedures. 1 All metal salts and DMF (N,N-dimethylformamide) (Sigma-Aldrich) were obtained from commercial sources and used without further purification. Elemental analyses (C, H and N) were performed on a Perkin-Elmer 240 CHN elemental analyzer. Powder X-ray diffraction measurements were recorded on a D/Max-2500 X-ray diffractometer using Cu Kα radiation. Thermal analyses (N2 atmosphere, heating rate of 5 C/min) were carried out in a Labsys NETZSCH TG 209 Setaram apparatus. Energy dispersive X-ray spectroscopy (EDX) was measured on a JEOL-7500F Microscope equipped with an energy dispersive spectroscopy (EDS) instrument. ICP was measured by ICP-9000(N+M) (USA Thermo Jarrell-Ash Corp). A portion of the research was performed using EMSL, a national scientific user facility sponsored by the Department of Energy's Office of Biological and Environmental Research and located at Pacific Northwest National Laboratory (USA). Syntheses of structures. For all structures, TGA and elemental analysis revealed the amount of solvent in the crystals and were taken into account to decide the formula unit and calculate the yield. Synthesis of 1a: Tetrakis[4-(carboxyphenyl)oxamethyl]methane acid (H 4 L) (30.8 mg, 0.05 mmol) and MnCl 2 4H 2 O (22 mg, 0.11mmol) were added to a mixture of (DMF) (4 ml) and H 2 O (100 µl) in a capped vial, sonicated to mix, and heated to 110 C for 72 followed by slow cooling to room temperature over 8 h. Block-shaped colorless crystals of 1a were obtained in a 72% yield (based on H 4 L). Elemental analysis calcd (%) for 1a SI 3
4 [Mn 3 (L) 2 ] 2-2[NH 2 (CH 3 ) 2 ] + 9DMF: C, 55.77; H, 5.93; N, 7.19%. Found: C, 55.28; H, 5.84; N, 7.42%. Synthesis of 1b: H 4 L (30.8 mg, 0.05 mmol) and MnCl 2 4H 2 O (22 mg, 0.11mmol) were added to a mixture of N,N-dimethylformamide (DMF) (4 ml) and H 2 O (1 ml) in a capped vial, sonicated to mix, and heated to 110 C for 24 h, followed by slow cooling to room temperature over 8 h. Bar-shaped colorless crystals of 1b were obtained in a 68% yield (based on H 4 L). Elemental analysis calcd (%) for 1b [Mn 3 (L) 2 ] 2-2H 3 O + 12DMF: C, 53.06; H, 5.98; N, 7.28%. Found: C, 52.09; H, 5.76; N, 6.78%. Note: one of the two solvated protons (2H 3 O + ) per formula unit balancing the framework charge were found by X-ray diffraction analysis but the other one is suggested by TGA and elemental analysis. Transformation of 1a (or 1b) to 2 and 3: Fresh colorless crystals of 1a (or 1b) were briefly dried on filter paper and prior to immersion in a DMF solution of either Co(NO 3 ) 2 or Ni(NO 3 ) 2 (to afford 2 and 3 respectively). Upon standing the color of the immersed crystals gradually changed to purple and light-green, respectively. The crystals of 2 and 3 were filtered and washed with DMF. Following this, cation-captured crystals were stored in fresh DMF for convenient observation and to further remove any residual surface impurities. Cation capture/exchange experiments: The fresh colorless crystals of 1a (or 1b) were briefly dried on the filter paper, and then 20mg crystals were immersed in 2 ml DMF solution of M(NO 3 ) 2 xh 2 O (M=Zn, Cu, Co, Ni, Mg, Ca, Sr) or YNO3 (Y=Li, Na) with a molarity of 0.2 M/L (0.1 M/L for Sr 2+ ). After three days, the crystals were filtered and washed with sufficient DMF to remove surface-absorbed cations. Then the crystals were examined by EDX or ICP-OES studies to decide the metal ratios (Table S1 and Table S2). For the selective metal ion capture experiments, the crystals were immersed in the blended DMF solution containing both metal SI 4
5 salts (0.2 M/L). For the UV-vis study of Co(II) ions capture process, 535mg (0.25mmol) crystals of 1a were soaked in 10 ml DMF solution of Co(NO 3 ) 2 6H 2 O (0.2 M/L). X-Ray Structure Determination:All crystallographic data (Table S3) were collected with a Bruker Kappa APEX II Single Crystal Diffractometer, which was equipped with graphite monochromatic Mo Kα radiation (λ = Å). Structures were solved by direct methods with the SHELXTL-97 program and refined by full-matrix least-squares techniques against F2 with the SHELXTL-97 program package. 2 All non-hydrogen atoms were refined anisotropically, and hydrogen atoms were located and refined isotropically. The contribution of disordered solvent molecules was treated as a diffuse using the Squeeze procedure in Platon. 3 The resulting new HKL4 files were used to further refine the structures. CCDC (1a), (1b), (2), (Cu- inserted 1a), and (3) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via References: [S1] Laliberte, D.; Maris, T.; Wuest, J. D. J. Org. Chem. 2004, 69, [S2] Sheldrick, G. M. SHELXS 97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, [S3] Spek, A. L. Appl. J. Crystallogr. 2003, 36, 7. SI 5
6 a) b) Figure S1. a) (Left) ORTEP Representation (30% probability) of the 1a asymmetrical unit; (Right) Crystallographic view of the porous framework of 1a along the a crystal axis, which is constructed of the Mn3 clusters (as SBUs) connected by L 4- linkers. The balanced NH 2 (CH 3 ) + 2 ions locate in one of the two channels. b) (Left) ORTEP Representation (30% probability) of the 1b asymmetrical unit; (Right) Crystallographic view of the porous framework of 1b along the a crystal axis shows the network has the same topology as 1a, with balanced H 3 O + ions occupying one of the two channels. (Grey: Carbon; Red: Oxygen; Cyan: Manganese; White: Hydrogen). The hydrogen atoms are omitted in the frameworks for clarity. SI 6
7 complex d (Å) θ ( ) a axis (Å) 1a b Figure S2. Comparison of L 4- conformers in 1a and 1b. SI 7
8 1a and 1b 2 3 1a-Cu Figure S3. The coordination modes of the L 4- ligand in complexes 1a, 1b, 2, 3 and 1a-Cu. (Grey: carbon; Red: Oxygen; Cyan: Manganese; Purple: Cobalt; Green: Nickel; Blue: Copper) SI 8
9 Figure S4. (Top) Crystallographic view of the intermediate structure of Cu-inserted 1a crystal (1a-Cu) along the b crystal axis (hydrogen atoms omitted for clarity; C, gray; O, red; Mn, cyan; Cu, purple). (Bottom): The coordination environments of metal ions in the 1a-Cu complex. SI 9
10 Figure S5. UV-vis absorption spectra of the 10 ml DMF solution of Co(NO 3 ) 2 with initial concentration of 0.2 M at various intervals, in which 1a crystals (0.25mmol) were soaked. (Inset) Plot of uptake of Co(II) by 1a crystals over a 48-h period. Figure S6. Plot of the χ M T versus T for complexes 1-3. The red solid lines represent the best fit obtained from the Hamiltonian given in the text and Curie-Weiss law. SI 10
11 a) b) Figure S7. a) (Left) ORTEP Representation (30% probability) of the 2 asymmetrical unit; (Right) Crystallographic view of the porous framework of 2 along the a crystal axis, which is constructed of the one-dimensional MnCo 3 infinite chains (as SBUs) connected by L 4- linkers. b) (Left) ORTEP Representation (30% probability) of the 3 asymmetrical unit; (right) Crystallographic view of the porous framework of 3 along the a crystal axis. (Grey: Carbon; Red: Oxygen; Cyan: Manganese; White: Hydrogen; Purple: Cobalt; Green: Nickel). The hydrogen atoms are omitted in the frameworks for clarity. SI 11
12 Figure S8. Crystal pictures of 1a, 2, 1-Cu, and 3 (from left to right). SI 12
13 Figure S9. PXRD patterns of as-synthesized samples of 1a, 2, 3 and Na + -exchanged 1a (1a-Na). SI 13
14 Figure S10. TGA curves for complex 1a, 1b, 2 and 3. The samples were heated to 550 C at a heating rate of 5 C/min. SI 14
15 a) b) c) Figure S11. Selected EDX spectra of TM 2+ -captured complex of 1a: (a) 2 with Co(II) uptake/exchange; (b): 1a-Cu with Cu(II) uptake/exchange; (c) 3 with Ni(II) uptake/exchange. The metal ratios in each complex are listed in Table S1. SI 15
16 Table S1. Metal ion analysis for the products after capture/exchange of divalent metal ions Sample EDX Fresh 1a Mn 100% Zn-captured product Zn 100%, no Mn Cu-captured product (intermediate phase) a Cu 77.18%, Mn 22.82% Cu-captured product (completed phase) b Cu 90.49%, Mn 9.51% Co-captured product (2) Co 75.88%, Mn 24.12% Ni-captured product (3) Ni 68.08%, Mn 31.92% Mg-captured product Mg 29.92%, Mn 70.08% Ca-captured product Ca 19.91%, Mn 80.09% Sr-captured product Sr 18.16%, Mn 81.84% 1a soaked in the blended DMF solution of Ca 2+ and Cu 2+ Cu 95.10%, Mn 4.90%, no Ca a 1a crystals were soaked in the DMF solution of Cu(II) nitrate for 16 hrs. The structure of the Cu-inserted crystals was successfully elucidated. b 1a crystals were soaked in the DMF solution of Cu(II) nitrate for 72 hrs. The crystals were found to lose single crystallinity. SI 16
17 a) b) Figure S12. Selected EDX spectra of complex 1a after metal ions uptake/exchange experiments: (a) Na + -exchanged sample of 1a; (b): Crystal 1a after soaking in the blended DMF solution of Na + and Co 2+. The metal ratios in each complex are listed in Table S2. SI 17
18 Table S2. Metal ion analysis for the products after selective metal cation capture/exchange between divalent metal ions (Co 2+ for example) and alkali metal ions (Na + and Li + ) Sample EDX Na + -exchanged compound Na 44.54%, Mn 55.46% 1a product soaked in a solution of Na + and Co 2+ Na 8.83%, Mn 22.11%, Co 69.05% *Li + -exchanged compound Li 36.14%, Mn 63.86% *1a after soaked in the blended solution of Li + and Co 2+ Mn 25.98%, Co 74.02%, no Li *The metal ratios are decided by ICP-OES study. SI 18
19 Table S3. Crystallographic parameters for 1a, 1b, 1a-Cu, 2 and 3 complexes 1a 1b 1a-Cu 2 3 formula C 35 H 30 Mn 1.5 N C 33 H 24 Mn 1.5 C 33 H 24 Cu 1.5 C 33 H 24 Co 1.5 C 33 H 24 Mn 0.5 Ni 1. O 12 O 12.5 Mn 0.5 O 13 Mn 0.5 O 13 5O 16 formula weight temperature (K) 100(2) 100(2) 100(2) 100(2) 100(2) wavelength (Å) crystal system triclinic triclinic triclinic triclinic triclinic space group P-1 P-1 P-1 P-1 P-1 a (Å) (4) (4) (8) (4) (7) b (Å) (6) (4) (10) (5) (6) c (Å) (6) (4) (10) (6) (7) α ( ) (2) (10) (4) (2) (2) β ( ) (2) (2) (3) (2) (2) γ ( ) (2) (2) (3) (2) (2) volume (Å 3 ) (17) (14) (3) (16) (2) Z Dc (g cm -3 ) µ (mm -1 ) GOF data collected/ R int 38270/ / / / / R1, wr2 (I > 2σ(I)) , , , , , R1, wr2 (all data) , , , , , SI 19
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