Self-Assembly of Chiral Metal-Organic Tetartoid
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1 Supporting Information for Self-Assembly of Chiral Metal-Organic Tetartoid Dong Luo,, Xue-Zhi Wang,, Chen Yang, Xiao-Ping Zhou*, and Dan Li*, College of Chemistry and Materials Science, Jinan University, Guangzhou , P. R. China. Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Guangdong , P. R. China. Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China These authors contributed equally to this work. S1
2 Syntheses of the Complexes General Procedure Starting materials, reagents, and solvents were purchased from commercial sources (Alfa Aesar, J&K, TCI and Aldrich) and used without further purification. FT-IR spectra were measured using a Nicolet Avatar 360 FT-IR spectrophotometer (vs = very strong, s = strong, m = middle, w = weak). Thermogravimetric analysis (TGA) was carried out in a nitrogen stream using Q50 TGA (TA) thermal analysis equipment with a heating rate of 10 C min 1. Powder X-ray diffraction (PXRD) patterns of the bulk samples were measured on a Ultima Ⅳ X-ray Diffractometer and Mini FLex600 Benchtop X-ray Diffractometer (Cu K, = Å). Elemental analyses were carried out with an Elementar vario EL Cube equipment. The solid UV-vis spectra and CD spectra were recorded on a Bio-Logic MOS-450 multifunctional circular dichroism spectrometer with KCl pellets. Low-pressure (up to 1 bar) gas adsorption isotherms (N2 and CO2) were measured on a Micrometrics ASAP 2020 Surface Area and Porosity Analyzer. ESI-TOF mass spectra were recorded on a Bruker MaXis II UHR-TOF mass spectrometer. Data analyses and simulations of ESI-TOF mass spectra were processed on a Bruker Data Analysis software. Syntheses of 1 to 6 Synthesis of 1: A mixture of Co(BF4)2 6H2O (17.0 mg, 0.05 mmol), 2-methyl-1H-imidazole-4-carbaldehyde (6.6 mg, 0.06 mmol), m-xylylenediamine (4.1 mg, 0.03 mmol), and N,N -dimethylformamide (DMF)/methanol mixed solvent (2.5 ml, 4:1, v/v) was sealed in a Pyrex glass tube and heated in an oven at 100 C for 72 hours and cooled to room temperature at a rate of 5 C/h. Deep red polyhedron-like crystals were obtained (6.0 mg, yield 32.3%, based on Co(BF4)2 6H2O). IR spectrum (KBr, pellets, cm -1 ): (s), (w), (w), (vs), (w), (w), (m), (w), (w), (w), (m), (m), (vs), (w), (w), (w), (w), (w), (w), (w). Elemental analysis (CHN), Co20C239H395B8F32N77O75, (corresponding to [Co20(L1)12(OH)12(H2O)4] 8BF4 5DMF 8MeOH 46H2O), calculated (%): C 38.69, H 5.37, N 14.53; found (%): C 38.45, H 5.63, N Synthesis of 2: A mixture of Co(BF4)2 6H2O (17.0 mg, 0.05 mmol), S2
3 2,5-dimethyl-1H-imidazole-4-carbaldehyde (7.5 mg, 0.06 mmol), m-xylylenediamine (4.1 mg, 0.03 mmol) and DMF/methanol mixed solvent (1.25 ml, 4:1, v/v) was sealed in a Pyrex glass tube and heated in an oven at 100 C for 72 hours and cooled to room temperature at a rate of 5 C/h. Deep red polyhedron-like crystals were obtained with low yield (2.0 mg). IR spectrum (KBr, pellets, cm -1 ): (s), (w), (w), (w), (vs), (m), (m), (m), (s), (w), (w), (w), (m), (m), (s), (w), (w), (m), (s), (m), (w), (w), (m). Elemental analysis (CHN), C252H398B8Co20F32N74O62, (corresponding to [Co20(L2)12(OH)12(H2O)4] 8BF4 2DMF 6MeOH 38H2O), calculated (%): C 41.30, H 5.47, N 14.14; found (%): C 40.77, H 5.28, N Synthesis of 3: A mixture of Co(BF4)2 6H2O (17.0 mg, 0.05 mmol), 2-methyl-1H-imidazole-4-carbaldehyde (6.6 mg, 0.06 mmol), m-xylylenediamine (4.1 mg, 0.03 mmol), tetraethylammonium perchlorate (45.9 mg, 0.2 mmol) and DMF/methanol mixed solvent (2.5 ml, 4:1, v/v) was sealed in a Pyrex glass tube and heated in an oven at 100 C for 72 hours and cooled to room temperature at a rate of 5 C/h. Deep red polyhedron-like crystals were obtained (15.0 mg, yield 75.2 %, based on Co(BF4)2 6H2O). IR spectrum (KBr, pellets, cm -1 ): (s), (w), (w), (vs), (m), (m), (s), (w), (m), (s), (s), (s), (w), (w), (w), (m), (w), (w), (w), (w), (w), (w). Elemental analysis (CHN), Co20C248H445Cl8N79O124, (corresponding to [Co20(L1)12(OH)12(H2O)4] 8ClO4 7DMF 11MeOH 58H2O), calculated (%): C 37.33, H 5.62, N 13.87; found (%): C 37.16, H 5.92, N Synthesis of 4: A mixture of Co(BF4)2 6H2O (13.6 mg, 0.04 mmol), 2-methyl-1H-imidazole-4-carbaldehyde (6.6 mg, 0.06 mmol), m-xylylenediamine (4.1 mg, 0.03 mmol), tetraethylammonium hexafluorophosphate (44.0 mg, 0.16 mmol) and N,N - dimethylacetamide (DMA)/methanol mixed solvent (3.0 ml, 2:1, v/v) was sealed in a Pyrex glass tube and heated in an oven at 100 C for 72 hours and cooled to room temperature at a rate of 5 C/h. Deep red polyhedron-like crystals were obtained with low yield (0.5 mg). IR spectrum (KBr, pellets, cm -1 ): (s), (w), (w), (vs), (w), (w), (s), (w), (w), (s), (m), (m), S3
4 847.02(vs), (w), (w), (w), (w), (w), (w), (w), (w). Elemental analysis (CHN), C226H405Co20F48N73O91P8, (corresponding to [Co20(L1)12(OH)12(H2O)4] 8PF6 DMA 6MeOH 68H2O), calculated (%): C 34.19, H 5.14, N 12.88; found (%): C 34.55, H 4.97, N Synthesis of 5: A mixture of Co(BF4)2 6H2O (17.0 mg, 0.05 mmol), 2-methyl-1H-imidazole-4-carbaldehyde (6.6 mg, 0.06 mmol), m-xylylenediamine (4.1 mg, 0.03 mmol), tetraethylammonium trifluoromethanesulfonate (55.9 mg, 0.2 mmol) and DMF/methanol mixed solvent (2.5 ml, 4:1, v/v) was sealed in a Pyrex glass tube and heated in an oven at 100 C for 72 hours and cooled to room temperature at a rate of 5 C/h. Deep red polyhedron-like crystals were obtained (13.3 mg, yield 58.9 %, based on Co(BF4)2 6H2O). IR spectrum (KBr, pellets, cm -1 ): (s), (w), (w), (w), (vs), (m), (m), (s), (w), (s), (w), (vs), (m), (m), (w), (w), (m), (w), (w), (w), (w), (m), (w), (w), (w), (w), (w). Elemental analysis (CHN), Co20C280H502F24N90O126S8, (corresponding to [Co20(L1)12(OH)12(H2O)4] 8OTf 18DMF 2MeOH 66H2O), calculated (%): C 37.22, H 5.60, N 13.95, S 2.84; found (%): C 36.96, H 5.35, N 14.18, S Synthesis of 6: A mixture of Co(NO3)2 6H2O (11.6 mg, 0.04 mmol), 1H-imidazole-4-carbaldehyde (5.8 mg, 0.06 mmol), m-xylylenediamine (4.1 mg, 0.03 mmol) and DMA/methanol mixed solvent (3.0 ml, 2:1, v/v) was sealed in a Pyrex glass tube and heated in an oven at 100 C for 72 hours and cooled to room temperature at a rate of 5 C/h. Deep red block crystals were obtained. IR spectrum (KBr, pellets, cm -1 ): (m), (w), (w), (w), (vs), (s), (m), (m), (m), (w), (m), (m), (w), (w), (s), (s), (m), (w), (w), (m), (m), (m), (m), (w), (w), (w), (w). Synthesis of ΛΛΛΛ-1 or -1: An in-situ induction method was adopted to obtain the homochiral tetartoidal cages. A mixture of Co(BF4)2 6H2O (17.0 mg, 0.05 mmol), 2-methyl-1H-imidazole-4-carbaldehyde (6.6 mg, 0.06 mmol), m-xylylenediamine (4.1 mg, 0.03 mmol), (L)-menthol (for ΛΛΛΛ-1, 0.06 mmol, 9.4 mg) or (D)-menthol (for -1, S4
5 0.06 mmol, 9.4 mg), and N,N -dimethylformamide (DMF)/methanol mixed solvent (2.5 ml, 4:1, v/v) was sealed in a Pyrex glass tube and heated in an oven at 100 C for 72 hours and cooled to room temperature at a rate of 5 C/h. Deep red polyhedron-like crystals were obtained. Crystal Structure Analysis and Additional Characterization Crystallographic Studies Single crystal structures of 1 to 6 were measured by X-ray diffraction. Data collection was performed on a XtaLab PRO MM007HF DW Diffractometer System equipped with a MicroMax-007DW MicroFocus X-ray generator and Pilatus 200K silicon diarray detector (Rigaku, Japan, Cu Kα, λ = Å). Crystals of 1 to 5 were measured at 100 K and 6 was measured at 293 K. The structure was solved by direct methods and refined by full-matrix least-squares refinements based on F2. Anisotropic thermal parameters were applied to all non-hydrogen atoms. The hydrogen atoms were generated geometrically. The crystallographic calculations were performed using the SHELXL-2014/7 programs. The treatment for the disordered guest molecules in the cavities of all complexes involved the use of the SQUEEZE program of PLATON. Crystal data and structure refinement were summarized in Table S1-S6. CCDC nos S5
6 Table S1 Summary of Crystal Data and Structure Refinement Parameters for 1. Parameter ΛΛΛΛ-1-1 Chemical formula C216H224BN72O16F4Co20 C216H224BN72O16F4Co20 Formula weight Crystal system Cubic Cubic Space group F23 F23 a (Å) (4) (3) b (Å) (4) (3) c (Å) (4) (3) (deg) β (deg) (deg) V (Å 3 ) (13) (11) Z 4 4 Dcalcd(g cm -3 ) μ (mm -1 ) Reflections collected Unique reflections Rint Goodness-of-fit on F R1 a [I > 2σ(I)] wr2 b [I > 2σ(I)] R1 a [all refl.] wr2 b [all refl.] CCDC number Flack parameter 0.003(9) 0.005(6) a R1= ( F0 - Fc )/ F0 ; b wr2=[ w(f0 2 - Fc 2 ) 2 / w(f0 2 ) 2 ] 1/2 S6
7 Table S2 Summary of Crystal Data and Structure Refinement Parameters for 2. Parameter ΛΛΛΛ-2-2 Chemical formula C240H272BN72O16F4Co20 C240H272BN72O16F4Co20 Formula weight Crystal system Cubic Cubic Space group F23 F23 a (Å) (3) (3) b (Å) (3) (3) c (Å) (3) (3) (deg) β (deg) (deg) V (Å 3 ) (10) (9) Z 4 4 Dcalcd(g cm -3 ) μ (mm -1 ) Reflections collected Unique reflections Rint Goodness-of-fit on F R1 a [I > 2σ(I)] wr2 b [I > 2σ(I)] R1 a [all refl.] wr2 b [all refl.] CCDC number Flack parameter 0.014(6) 0.002(7) a R1= ( F0 - Fc )/ F0 ; b wr2=[ w(f0 2 - Fc 2 ) 2 / w(f0 2 ) 2 ] 1/2 S7
8 Table S3 Summary of Crystal Data and Structure Refinement Parameters for 3. Parameter ΛΛΛΛ-3-3 Chemical formula C216H224N72O20ClCo20 C216H224N72O20ClCo20 Formula weight Crystal system Cubic Cubic Space group F23 F23 a (Å) (4) (4) b (Å) (4) (4) c (Å) (4) (4) (deg) β (deg) (deg) V (Å 3 ) (13) (13) Z 4 4 Dcalcd(g cm -3 ) μ (mm -1 ) Reflections collected Unique reflections Rint Goodness-of-fit on F R1 a [I > 2σ(I)] wr2 b [I > 2σ(I)] R1 a [all refl.] wr2 b [all refl.] CCDC number Flack parameter 0.034(11) 0.040(10) a R1= ( F0 - Fc )/ F0 ; b wr2=[ w(f0 2 - Fc 2 ) 2 / w(f0 2 ) 2 ] 1/2 S8
9 Table S4 Summary of Crystal Data and Structure Refinement Parameters for 4. Parameter ΛΛΛΛ-4-4 Chemical formula C216H224N72O16F42P7Co20 C216H224N72O16F42P7Co20 Formula weight Crystal system Cubic Cubic Space group F23 F23 a (Å) (4) (2) b (Å) (4) (2) c (Å) (4) (2) (deg) β (deg) (deg) V (Å 3 ) (14) (7) Z 4 4 Dcalcd(g cm -3 ) μ (mm -1 ) Reflections collected Unique reflections Rint Goodness-of-fit on F R1 a [I > 2σ(I)] wr2 b [I > 2σ(I)] R1 a [all refl.] wr2 b [all refl.] CCDC number Flack parameter (5) 0.18(2) a R1= ( F0 - Fc )/ F0 ; b wr2=[ w(f0 2 - Fc 2 ) 2 / w(f0 2 ) 2 ] 1/2 S9
10 Table S5 Summary of Crystal Data and Structure Refinement Parameters for 5. Parameter ΛΛΛΛ-5-5 Chemical formula C217H224N72O19Co20F3S C217H224N72O19Co20F3S Formula weight Crystal system Cubic Cubic Space group F23 F23 a (Å) (3) (3) b (Å) (3) (3) c (Å) (3) (3) (deg) β (deg) (deg) V (Å 3 ) (5) (11) Z 4 4 Dcalcd(g cm -3 ) μ (mm -1 ) Reflections collected Unique reflections Rint Goodness-of-fit on F R1 a [I > 2σ(I)] wr2 b [I > 2σ(I)] R1 a [all refl.] wr2 b [all refl.] CCDC number Flack parameter 0.035(6) (7) a R1= ( F0 - Fc )/ F0 ; b wr2=[ w(f0 2 - Fc 2 ) 2 / w(f0 2 ) 2 ] 1/2 S10
11 Table S6 Summary of Crystal Data and Structure Refinement Parameters for 6. Parameter 6 Chemical formula C96H84N42O18Co8 Formula weight Crystal system Triclinic Space group P-1 a (Å) (5) b (Å) (6) c (Å) (5) (deg) (3) β (deg) (2) (deg) (3) V (Å 3 ) (4) Z 2 Dcalcd(g cm -3 ) μ (mm -1 ) Reflections collected Unique reflections Rint Goodness-of-fit on F R1 a [I > 2σ(I)] wr2 b [I > 2σ(I)] R1 a [all refl.] wr2 b [all refl.] CCDC number a R1= ( F0 - Fc )/ F0 ; b wr2=[ w(f0 2 - Fc 2 ) 2 / w(f0 2 ) 2 ] 1/2 S11
12 Figure S1. PXRD patterns for simulated (black line) and as-synthesized (red line) samples of tetartoid 1 (up) and 2 (bottom). S12
13 Figure S2. Four types of dodecahedra based on pentagons. ( Figure S3. Cobaltite from Sweden ( S13
14 The positive coordination cage [Co20L112(OH)12(H2O)4] 8+ in 1 is linked by BF4 - anions to form a diamond-like framework (Figure S4), which is similar to our previous reported mesoporous supramolecular framework assembled from cubic cages and anions. S1 Weak C-H F and edge to face interactions (C-H ) are observed (Figure S4b), which probably play a structure direction role to assemble the tetartoids to the 3-dimensional extended framework. Notable, due to the chiral property of tetartoid, the assembled supramolecular framework is also chiral. The framework of 1 is porous, and the potential solvent-accessible void volume is 18085Å 3 in one unit cell, with 48.4 % checked by PLATON. Anions BF4 - and solvent molecules (e.g. DMF, methanol) filled the cavities. The cavity s size (space between the cages) is about Å (distance between two opposite square pyramidal Co(II) centers belonged to two diagonal cages, Figure S4c), providing potential porous materials for gas adsorption and separation. (S1) Luo, D.; Zhou, X.-P.; Li, D. Angew. Chem., Int. Ed. 2015, 54, S14
15 Figure S4. (a) Three-dimensional structure of supramolecular framework based on tetartoid -1 and BF4-. (b) BF4- ion is surrounded by four tetartoid (C-H F interactions and C-H interactions are observed and are highlighted by red and yellow dashed line, respectively). (c) One diamond unit of supramolecular framework (green ball representing the central cavity). (d) Simplified diagram of the one diamond unit in the supramolecular (green ball representing the outer cavity, yellow ball representing the inner cavity of tetartoid -1, blue tetrahedron representing the anion BF4-). Color codes for elements: Co cyan, C gray, N blue, O red, B dark green, F green, H light gray. H atoms in (c) are omitted for clarity. S15
16 Figure S5. (a) ESI-TOF mass spectrum of 1. (b) Expanded spectra for 26 species {[Co20L112(OH)12(H2O)w(CH3CN)x] 4BF4 yh2o zmeoh} 4+ (peaks a-z: w = 0-4, x = 0-4, y = 0-4, z = 0-7). Insets show the observed and simulated isotopic patterns of the peaks at m/z (peak f) corresponding to a mixture of {[Co20L112(OH)12(H2O)4] 4BF4 MeOH} 4+. Preparing acetonitrile (CH3CN) solution of 1: the bulk sample of 1 (3 mg) was added to CH3CN (5 ml) and the mixture was heated at 65 for 12 hours and cooled to room temperature. After filtration, the filtrate was used for mass spectrum measurement. S16
17 Figure S6. The expanded spectra of the +4 target species: peak (a) {[Co20L112(OH)12(H2O)2] 4BF4} 4+, peak (b) {[Co20L112(OH)12(H2O)] 4BF4 MeOH} 4+, peak (c) {[Co20L112(OH)12] 4BF4 2MeOH} 4+, peak (d) {[Co20L112(OH)12(CH3CN)] 4BF4 MeOH}, peak (e) {[Co20L112(OH)12(H2O)(CH3CN)] 4BF4 MeOH} 4+, peak (f) {[Co20L112(OH)12(H2O)4] 4BF4 MeOH} 4+, peak (g) {[Co20L112(OH)12(H2O)3] 4BF4 2MeOH} 4+, peak (h) {[Co20L112(OH)12(H2O)2] 4BF4 3MeOH} 4+, peak (i) {[Co20L112(OH)12(H2O)3(CH3CN)] 4BF4 H2O MeOH} 4+. Red: observed isotope patterns; black: simulated isotope patterns. S17
18 Figure S7. The expanded spectra of the +4 target species: peak (j) {[Co20L112(OH)12(H2O)3(CH3CN)] 4BF4 2MeOH} 4+, peak (k) {[Co20L112(OH)12(H2O)4] 4BF4 4H2O MeOH} 4+, peak (l) {[Co20L112(OH)12(H2O)4] 4BF4 3H2O 2MeOH} 4+, peak (m) {[Co20L112(OH)12(H2O)4] 4BF4 2H2O 3MeOH} 4+, peak (n) {[Co20L112(OH)12(H2O)4] 4BF4 H2O 4MeOH} 4+, peak (o) {[Co20L112(OH)12(H2O)4] 4BF4 5MeOH} 4+, peak (p) {[Co20L112(OH)12(CH3CN)4] 4BF4 H2O 2MeOH} 4+, peak (q) {[Co20L112(OH)12(CH3CN)4] 4BF4 3MeOH} 4+, peak (r) {[Co20L112(OH)12(H2O)(CH3CN)3] 4BF4 2H2O 3MeOH} 4+. Red: observed isotope patterns; black: simulated isotope patterns. S18
19 Figure S8. The expanded spectra of the +4 target species: peak (s) {[Co20L112(OH)12(H2O)(CH3CN)3] 4BF4 H2O 4MeOH} 4+, peak (t) {[Co20L112(OH)12(H2O)(CH3CN)3] 4BF4 5MeOH} 4+, peak (u) {[Co20L112(OH)12(CH3CN)4] 4BF4 3H2O 3MeOH} 4+, peak (v) {[Co20L112(OH)12(CH3CN)4] 4BF4 2H2O 4MeOH} 4+, peak (w) {[Co20L112(OH)12(CH3CN)4] 4BF4 H2O 5MeOH} 4+, peak (x) {[Co20L112(OH)12(CH3CN)4] 4BF4 6MeOH} 4+, peak (y) {[Co20L112(OH)12(H2O)(CH3CN)3] 4BF4 2H2O 6MeOH} 4+, peak (z) {[Co20L112(OH)12(H2O)(CH3CN)3] 4BF4 H2O 7MeOH} 4+. Red: observed isotope patterns; black: simulated isotope patterns. S19
20 Figure S9. The expanded spectra of the +5 target species: peak (a) {[Co20L112(OH)12(H2O)(CH3CN)] 3BF4 MeOH} 5+, peak (b) {[Co20L112(OH)12(H2O)4] 3BF4 2H2O} 5+, peak (c) {[Co20L112(OH)12(H2O)3] 3BF4 2MeOH} 5+, peak (d) {[Co20L112(OH)12(H2O)2] 3BF4 3MeOH} 5+, peak (e) {[Co20L112(OH)12(H2O)] 3BF4 4MeOH} 5+, peak (f) {[Co20L112(OH)12] 3BF4 5MeOH} 5+, peak (g) {[Co20L112(OH)12(H2O)4] 3BF4 4H2O MeOH} 5+, peak (h) {[Co20L112(OH)12(H2O)4] 3BF4 3H2O 2MeOH} 5+. Red: observed isotope patterns; black: simulated isotope patterns. S20
21 Figure S10. The expanded spectra of the +3 target species: peak (a) {[Co20L112(OH)12(H2O)2] 5BF4 MeOH} 3+, peak (b) {[Co20L112(OH)12(H2O)2(CH3CN)] 5BF4} 3+, peak (c) {[Co20L112(OH)12(H2O)(CH3CN)] 5BF4 MeOH} 3+, peak (d) {[Co20L112(OH)12(H2O)4] 5BF4 MeOH} 3+, peak (e) {[Co20L112(OH)12(H2O)3] 5BF4 2MeOH} 3+, peak (f) {[Co20L112(OH)12(H2O)2] 5BF4 3MeOH} 3+, peak (g) {[Co20L112(OH)12(H2O)] 5BF4 4MeOH} 3+. Red: observed isotope patterns; black: simulated isotope patterns. S21
22 Figure S11. The narrow pore size (H H 2.691Å) of the pentagonal window in tetartoid 1. Color codes for elements: Co cyan, C gray, N blue, O red, H light gray. Figure S12. Photographs of 6 selected crystals of 1 for SCXRD data collection and solid CD spectra. S22
23 Table S7 A summary of structure determinations of 6 randomly selected crystals for 1: cell parameters, R factors, Flack parameters and observed absolute configurations are listed. V R1 wr2 Flack parameter Absolute configuration I (5) (16) (8) ΛΛΛΛ-1 II (4) (13) (7) ΛΛΛΛ-1 III (4) (12) (14) ΛΛΛΛ-1 IV (5) (17) (8) ΔΔΔΔ-1 V (6) 36381(2) (11) ΔΔΔΔ-1 VI (5) (15) (10) ΔΔΔΔ-1 Figure S13. Solid-state CD spectra of 6 selected crystals of 1 (correspond to the above table). S23
24 Figure S14. PXRD patterns of as-synthesized ΛΛΛΛ-1 (blue line) and -1 (red line) compare with simulated pattern of conglomerate 1 (black line). Figure S15. Solid-state CD spectra recorded for bulk samples of 5 parallel experiments for the ΛΛΛΛ-1 or -1 synthesized in the presence of (L)-menthol or (D)-menthol. Sample preparation: about 2 mg crystals are combined with KCl (25 mg) to get a pellet under 10 MPa pressure for CD spectrum measurement. S24
25 Single crystal X-ray diffraction analysis found that 6 crystallize in the triclinic P-1 space group. As shown in Figure S17, cobalt ions were coordinated by bis-imidazole ligands H2L4 (H2L4 = 1,3-bis[(1H-imidazol-4-yl)methyleneaminomethyl]benzene) to form a 8-nucleus cubic cage. The bis-imidazole ligand L was in situ formed by the condensation of 4-formylimidazole and m-xylylenediamine, which is further documented by its IR spectrum (C=N feature absorbance peak around 1606 cm -1 in Figure S21). Two cobalt ions in the cubic cage adopt octahedral coordination geometry, and each one is chelated by three L4, with Co-N (imidazole) bond lengths ranging from 1.892(5) to 1.905(5) Å. The shorter Co-N bonds indicate that the octahedral Co has a valence of +3, and the Co(III) is probably yielded by the oxidization of Co(II) by oxygen during the reaction. Interestingly, two Co(III) ions with L4 around them have opposite asymmetric arrangements, and as a whole the Co-imidazolate cage is achiral. The other six Co ions in the cage adopt distorted octahedral geometry and each Co is coordinated by four nitrogen atoms and two oxygen atoms (from nitrate) with Co-N (imidazole) bond lengths from 2.020(5) to 2.068(5) Å, which are obviously longer than the Co(III)-N bonds, indicating these Co ions of a valence of +2. The edge lengths in the Co-imidazolate cubic cage 6 are around 6.1 Å (6.042 Å Å, Co Co distance), and the volume is about 227 Å. S25
26 Figure S16. Square window in cubic cobalt-imidazolate cage [Co8L36(H2O)6] 6BF4 guests (dashed red line highlighted the short H H distances). Color codes for elements: Co cyan, C gray, N blue, O red, H light gray. Figure S17. SCXRD structure of cubic cage 6. Color codes for elements: Co cyan, C gray, N blue, O red, H light gray. Large yellow ball represents the cavity of cage 6. S26
27 Tetartoids 1 and 5 are chosen to evaluate the permanent porosity for their relative high yields. Before gas adsorption studies, 1 and 5 were solvent-exchanged with methanol for 3 days, followed by evacuation under vacuum at room temperature for 12 h. N2 adsorptions were measured at 77 K. Both samples exhibited type I isotherms (Figure S18), suggesting the permanent microporous properties. The Brunauer-Emmett-Teller (BET) and Langmuir surface areas for 1 and 5 are calculated to be 145 and 447 m 2 /g, 269 and 593 m 2 /g, respectively. The big difference of porosity is probably due to different stability under vacuum conditions. PXRD measurements of the samples after gas adsorption shown that the crystallinity of 5 is better than that of 1 (Figure S19), indicating that 1 lost partial porosity. However, as shown in Figure S20, their uptake abilities of CO2 (1 58 and 5 61 cm 3 /g) and N2 (1 3.6 and cm 3 /g ) at 273 K and 100 KPa is similar. The capacity of gas adsorption for 1 and 5 is moderate, which is compared to some porous materials based on coordination cage. S2 (S2) a) Dai, F.-R.; Wang, Z. J. Am. Chem. Soc. 2012, 134, 8002; b) Wang, X.-S.; Chrzanowski, M.; Gao, W.-Y.; Wojtas, L.; Chen, Y.-S.; Zaworotko, M. J.; Ma, S. Chem. Sci. 2012, 3, S27
28 Figure S18. N2 77 K adsorption isotherms (up) and DFT pore width (bottom) of 1 and 5. Activation condition: 1 and 5 were solvent-exchanged with methanol for 3 days, followed by direct evacuation under vacuum at room temperature for 12 h before gas adsorption measurement. S28
29 Figure S19. PXRD patterns of 1 and 5 after N2 77 K adsorption measurement. Figure S20. CO2 195 K adsorption isotherms (left) and CO2/N2 273 K adsorption isotherms (right) of 1 and 5. S29
30 All cage compounds (1 to 6) were characterized by IR spectra, showing a strong absorption peak at around cm -1 (Figure S21), which showed that the dynamic imine bonds (C=N) were formed in the subcomponent self-assembly. Meanwhile, characteristic absorption peaks of corresponding anions (BF4 -, ClO4 -, PF6 - and OTf - ) were involved in the IR spectra of these compounds (Figure S21). The thermogravimetric analyses (TGA) indicated they all had moderate thermal stability with a decomposing temperature around 300 C (Figure S22). The powder X-ray diffraction (PXRD) measurements revealed that the bulk 3 to 5 had uniform crystalline in the solid state (Figure S23). S30
31 Figure S21. IR spectra of 1 to 6. Figure S22. TGA plots of as-synthesized 1 to 5. S31
32 Figure S23. PXRD patterns for simulated (black line) and as-synthesized (red line) samples of 3 to 5. Figure S23 Solid-state UV-vis spectrum of tetartoid 1. S32
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