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1 Supporting Information pyright Wiley-VCH Verlag GmbH &. KGaA, Weinheim, 2008
2 Time-Evolving Self-rganization and Autonomous Structural Adaptation of balt(ii) rganic Framework Materials with Nets scu and pts Jing-Yun Wu, [a] Shang-Li Yang, [b] Tzuoo-Tsair Luo, [a] Yen-Hsiang Liu, [c] Yi-Wei Cheng, [a] Yen- Fu Chen, [b] Yuh-Sheng Wen, [a] Lee-Gin Lin, [b] and Kuang-Lieh Lu* [a] [a] Dr. J. Y. Wu, Dr. T. T. Luo, Y. W. Cheng, Y. F. Chen, Dr. Y. S. Wen, Prof. Dr. K. L. Lu Institute of Chemistry, Academia Sinica, Taipei, 115 (Taiwan) Fax: (+886) [b] S. L. Yang, Prof. Dr. L. G. Lin Department of Chemistry Chinese Culture University, Taipei 111 (Taiwan) [c] Prof. Dr. Y. H. Liu Department of Chemistry Fu Jen Catholic University, Taipei 242 (Taiwan) 1
3 Detailed Experimental Section General Details: Chemical reagents were purchased commercially and were used as received without further purification. Thermogravimetric analyses were performed under nitrogen with a Perkin-Elmer TGA-7 TG analyzer. Powder-diffraction measurements were recorded with a Siemens D-5000 diffractometer at 40 kv (30 ma) with Cu-Ka (? = Å), with a step of 0.02 in? and a scan speed of 1 sec per step size. Elemental analyses were conducted on a Perkin-Elmer 2400 CHN elemental analyzer. Syntheses of {K 2 [ 3 (btec) 2 (H 2 ) 4 ] 6H 2 } n (1) and {K 2 [(btec)] 7H 2 } n (2). In a tube at ambient temperature, a solution of Cl 2 6H 2 (95.8 mg, mmol) in EtH (5 ml) was carefully layered on top of a bilayer solution comprised of an aqueous solution (5 ml) containing tetrapotassium benzene-1,2,4,5-tetracarboxylate (K 4 btec, 81.6 mg, mmol) on the bottom and a buffer solvent of THF on the top. Scarlet crystals of 1 were produced within a 3-day period. After allowing the solution to stand for further seven days, violet crystals of 2 appeared. The crystals were washed with ethanol and deionized water, and dried in air. The powder X-ray diffraction patterns of the samples are in good agreement of the patterns simulated from the single-crystal diffraction data of 1 and 2 (Figure S7). For 1: Yield: 80% based on K 4 btec (75.3 mg, mmol). Anal. Calcd for C 20 H 24 3 K 2 26 : C, 25.68; H, Found: C, 25.24; H, For 2: Yield: 1% based on K 4 btec (1.4 mg, mmol). Anal. Calcd for C 10 H 16 K 2 15 : C, 23.40; H, Found: C, 23.42; H, Following a similar procedure, Cl 2 6H 2 (38.5 mg, mmol) and K 4 btec (82.9 mg, mmol), at a low II /K I (1:5) ratio, were introduced into the reaction system. The scarlet crystals of 1 was initially formed after the self-assembly system was allowed to stand for the first several days at ambient temperature. Along with 1, violet crystals of 2 were formed. Because this supramolecular system is not totally homogenerous, both compound 1 and 2 can be forming for a further period of time. Yield of 1: 46% based on Cl 2 6H 2 (23.2 mg, mmol). Yield of 2: 47% based on Cl 2 6H 2 (39.5 mg, mmol). 2
4 Synthesis of 1 as the only product. Following a similar procedure, in a tube at ambient temperature, a solution of Cl 2 6H 2 (190.9 mg, mmol) in EtH (5 ml) was carefully layered on top of a bilayer solution comprised of an aqueous solution (5 ml) containing K 4 btec (83.2 mg, mmol) on the bottom and a buffer solvent of THF on the top. Scarlet crystals (92.3 mg, mmol, 96% yield based on K 4 btec) of 1 were produced in a 3-day period. Synthesis of 2 as the only product. Following a similar procedure, in a tube at ambient temperature, a solution of Cl 2 6H 2 (190.8 mg, mmol) in EtH (5 ml) was carefully layered on top of a bilayer solution comprised of an aqueous solution (5 ml) containing K 4 btec (81.4 mg, mmol) and KCl (151.7 mg, 2.0 mmol) on the bottom and a buffer solvent of THF on the top. Violet crystals (69.8 mg, mmol, 68% yield based on K 4 btec) of 2 were obtained as the only product in a 10-day period. Syntheses of 1 and 2 in Different II /K I Ratios in the Addition of Extra KCl Salt. As shown in Table 1, a series of experiments, using a fixed metal-to-ligand ratio (Cl 2 6H 2, 0.8 mmol; K 4 btec, 0.2 mmol), but with different amounts of KCl ( mmol) added were carried out. In the absence of KCl, compound 1 was obtained as an only product in near quantitative yield. When 0.1 mmol of KCl was added to the self-assembly system, a much lower amount of compound 1 was formed (final yield, 51%), while 2 was generated in a yield of 23%. ntinuing to increase the amount of KCl in the selfassembly systems, the yield of 2 was found to be increased whilst that of 1 was decreased. Crystal structure determination. Suitable single crystals of 1 and 2 were mounted on the tip of a glass fiber with dimensions of mm 3 and mm 3, respectively and placed onto the goniometer head for indexing and intensity data collection using an Enraf-Nonius CAD4 diffractometer equipped with graphite monochromatized Mo Kα radiation (λ = Å). Empirical absorptions were applied 3
5 using the psi-scan method. Both structures were solved by direct methods, and refined against F 2 by the full-matrix least-squares technique using the WINGX, [1] PLATN, [2] and SHELX [3] software packages. Anisotropical thermal factors were assigned to non-hydrogen atoms. The positions of the C H hydrogen atoms were generated geometrically, assigned isotropic thermal parameters. In 1, the potassium atoms are disordered over two positions with a site-occupation factor (S..F.) of 0.5. The positions of the hydrogen atoms of bridging water molecules were located from difference Fourier maps, and no attempt was made to locate the hydrogen atoms of guest water molecules. Crystal data for 1: C 20 H 24 3 K 2 26, M r = , monoclinic, C2/m, a = (2) Å, b = (1) Å, c = 9.467(1) Å, ß = (1), V = (4) Å 3, Z = 2, ρ calcd = g cm 3, µ = mm 1, F(000) = 942, T = 293(2) K. A total of 1606 reflections were collected in the range of θ = , of which 1510 were unique (R int = ). Final R indices: R 1 = , wr 2 = for 1405 reflections [I > 2σ (I)]; R 1 = , wr 2 = for 1510 independent reflections (all data) and 143 parameters, GF = Crystal data for 2: C 10 H 16 K 2 15, M r = , monoclinic, C2/c, a = (1) Å, b = (3) Å, c = (2) Å, ß = 90.95(1), V = (6) Å 3, Z = 4, ρ calcd = g cm 3, µ = mm 1, F(000) = 1044, T = 293(2) K. A total of 1803 reflections were collected in the range of θ = , of which 1713 were unique (R int = ). Final R indices: R 1 = , wr 2 = for 1472 reflections [I > 2σ (I)]; R 1 = , wr 2 = for 1713 independent reflections (all data) and 138 parameters, GF = References [1] L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837. [2] A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7. [3] G. M. Sheldrick, SHELX-97, University of Göttingen, Germany,
6 TGA analysis. Thermogravimetric analysis of 1 showed that guest water molecules were eliminated from the networks (calcd, 19.3%; found 19.5%) when the temperature was increased from room temperature to about 400 C, after which decomposition of the framework occurred. For 2, the release of guest and coordinated water molecules occurred in one step from 30 C to 180 C (found, 23.2%; calcd, 24.5%); 2 was thermally stable upon heating up to 350 C (Figure S6). Figure S1. ordination modes of the btec ligand in 1 (Left) and in 2 (Right). a) b) Figure S2. Local coordination environments of II centers in a) 1 and b) 2 (atoms are represented as 30% thermal ellipsoids); hydrogen atoms have been omitted for clarity (red =, cyan = oxygen, white = carbon). 5
7 a) b) c) Figure S3. a) The eight-connecting building unit in a distorted cubic geometry in 1 and its simplified view. b) Perspective view of the network of 1 simplified according to part (a). c) The (4,8)-connected net scu of 1. The btec ligand is simplified as a four connecting motif in a square-planar geometry (In part (a): red =, cyan = oxygen, white = carbon, orange = hydrogen). a) b) c) Figure S4. a) The four-connecting building unit in a distorted tetrahedral geometry in 2 and its simplified view. b) Perspective view of the network of 1 simplified according to part (a). c) The (4,4)- connected net pts of 2. 6
8 a) b) Figure S5. Water rods inside the network channels: a) {(H 2 ) 4 2(K 2 (H 2 ) 2 ) 4 } n in 1. The disordered K I ion and the disordered water molecule occupy the same position. b) {(H 2 ) 4 (H 2 ) 4 } n in 2. The green atoms represent disordered water molecules. Figure S6. Thermogravimetric (TG) analysis diagrams of 1 (solid line) and 2 (dashed line). 7
9 Simulated of 1 Simulated of 2 As-synthesized of 1 As-synthesized of 2 Figure S7. PXRD diagrams of 1 (left) and 2 (right). Table S1. Dynamic self-organization of 1 and 2 from Cl 2 6H 2 (M), K 4 btec (L) and KCl a. Entry KCl yield of 1 M : L : KCl II : K I b yield of 2 b (mmol) % mmol % mmol : 2: 0 8 : : 2: 1 8 : : 2: 2 8 : : 2: 3 8 : : 2: 4 8 : : 2: 5 8 : : 2: 10 8 : : 2: 20 8 : a Cl 2 6H 2 = 0.8 mmol, K 4 btec = 0.2 mmol. b The yield percentage is calculated based on the K 4 btec ligand. 8
10 Table S2. Selected bond lengths (Å) and angles (deg) for 1 a 1 2# (3) (3) 1 2# (3) 1 2# (3) 1 11# (4) 1 11# (4) 2 1# (3) 2 1# (3) 2 3# (3) (3) (5) (4) 2# (3) 2#1 1 2#2 89.6(2) 2 1 2#2 90.4(2) 2#1 1 2#3 90.4(2) 2 1 2#3 89.6(2) 2#2 1 2# (3) 2#1 1 11# (12) # (12) 2#2 1 11# (12) 2#3 1 11# (12) 2#1 1 11# (12) # (12) 2#2 1 11# (12) 2#3 1 11# (12) 11#4 1 11# (14) 1#5 2 1#6 94.6(2) 1#5 2 3# (13) 1#6 2 3# (13) 1# (13) 1# (13) 3# (18) 1# (13) 1# (13) 3# (13) (13) 1# (12) 1# (12) 3# (12) (12) (18) a Symmetry transformations: #1 x, y, z; #2 x, y, z; #3 x, y, z; #4 x 1/2, y 1/2, z; #5 x + 1/2, y + 1/2, z; #6 x + 1/2, y + 1/2, z; #7 x, y + 1, z. Table S3. Selected bond lengths (Å) and angles (deg) for 2 a 1 2# (2) (2) 1 2# (2) 1 4# (2) 4 1 2# (11) 4 1 2# (11) 4 1 4# (15) 2#1 1 2# (15) 2#1 1 4# (11) 2#2 1 4# (11) a Symmetry transformations: #1 x + 1, y, z + 2; #2 x, y, z + 1/2, #3 x + 1, y, z + 5/2. 9
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