Supporting Information. Crystal surface mediated structure transformation of kinetic framework. composed of multi-interactive ligand TPHAP and Co(II)
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1 Supporting Information Crystal surface mediated structure transformation of kinetic framework composed of multi-interactive ligand TPHAP and Co(II) Yumi Yakiyama, Akira Ueda, Yasushi Morita,* Masaki Kawano* Contents of Supplementary Information: 1. Methods Synthesis of K + TPHAP Syntheses of TPHAP-Co Kin, TPHAP-Co Therm -1 and TPHAP-Co- Therm -2 X-ray crystallographic data S2 S2 S3 2. Figures S1 S11 Fig. S1 ORTEP view of K + TPHAP CH 3 OH S5 Fig. S2 The N HO type hydrogen bonding interactions in a pore of TPHAP-Co Kin S5 Fig. S3 The N HO type hydrogen bonding interactions in a pore of TPHAP-Co Therm -1 S6 Fig. S4 AFM images of the surface of single crystal Co-TPHAP Kin S6 Fig. S5 The bond lengths of HAP skeletons in TPHAP-Co Kin crystal S7 Fig. S6 The bond lengths of HAP skeletons in two thermodynamically more stable crystals S7 Fig. S7 IR spectrum of K + TPHAP S8 Fig. S8 The face index of TPHAP-Co Kin crystal and the model picture S8 Fig. S9 The crystal structure of TPHAP-Co Therm -2 S9 Fig. S10 Temperature-dependent X-ray diffraction pattern change of TPHAP-Co Therm -1 S9 Fig. S11 The simulated void spaces of TPHAP-Co systems S10 Fig. S12 The CCD 2D-images of TPHAP-Co Kin crystals and the capillary pictures before and after in situ study S11 3. Reference S12 S1
2 Methods All chemicals and reagents were used as received. All reactions were performed at ambient temperature in air. UV/vis spectra were recorded on a Shimadzu UV/Vis-NIR scanning spectrophotometer UV-3600 PC using methanol solution (1.0 x 10 5 M). IR spectra were recorded on a Varian 670-IR FT-IR spectrometer in KBr pellets. The diffraction data for K + TPHAP were collected on a Bruker APEX II QUAZAR instrument in house. The diffraction data for TPHAP-Co Kin, TPHAP-Co Therm -1, and TPHAP-Co Therm -2 were collected on a RIGAKU/MSC Mercury CCD X-ray diffractometer with a synchrotron radiation ( = Å) at PF-AR (NW2A beamline) of the High Energy Accelerator Research Organization (KEK). The structures were solved by direct methods (SHELXS-97) and refined by full-matrix least squares calculations on F 2 (SHELXL-97) using the SHELX-TL program package. Elemental analyses were performed at Pohang University of Science and Technology. AFM images collection of TPHAP-Co Kin crystals AFM images of TPHAP-Co Kin crystals were measured on a VEECO Dimension 3100+Nanoscope V (Version 7.0) at National Center for Nanomaterials Technology (NCNT, Korea). After shaking the crystallization tube, we immediately picked up the single crystals and casted on a Si wafer after washing with EtOH twice. The images in 5 min or 10 min after shaking were also measured in the same way. Powder X-ray diffraction of TPHAP-Co crystals In situ powder X-ray diffraction of TPHAP-Co Kin crystals: Dozens of single crystals of TPHAP-Co Kin were loaded into a 0.7 mm capillary with a mother solution of the crystallization. In situ powder data were collected at 25 C on a Bruker APEX II QUAZAR instrument in house: the X-ray beam size, 100 m; scan, 360 rotation; exposure time, 180 sec. The 2D diffraction images were integrated with the FIT2D program to generate 1D powder diffraction data S1 If a mother solution of the crystallization for TPHAP-Co Kin was not provided enough, crystal transformation was not completed, leading to mixture of TPHAP-Co Kin and TPHAP-Co Therm -1. During diffraction measurement, a capillary was regularly shuffled by moving -axis to provide the mother solution to crystals and promote structure transformation smoothly. Temperature-dependent X-ray diffraction pattern change of TPHAP-Co Therm -1: Dozens of single crystals of TPHAP-Co Therm -1 were loaded into a 0.7 mm capillary with a mother solution of the crystallization. The crystals were collected and measured at 25 C firstly, then heated at 40 C for 12 h. The image data were collected at 25 C on a Bruker APEX II QUAZAR instrument in house: the X-ray beam size, 100 m; scan, 360 rotation; exposure time, 180 sec. The 2D diffraction images were integrated with the FIT2D program to generate 1D powder diffraction data. Synthesis of potassium 2,5,8-tri-(4 -pyridyl)-1,3,4,6,7,9-hexaazaphenalenate, K + TPHAP : 4-pyridylamidine hydrochloride (9.10 g, 57.7 mmol) and potassium tricyanomethanide (1.50 g, 11.6 mmol) were placed in a Teflon-lined stainless autoclave and heated at 200 ºC for 16 h. At this stage, a NMR yield of the product is about 62%. A 2M HCl aqueous solution was added to the reaction S2
3 mixture and washed with ethyl acetate. After removing ethyl acetate, the aqueous layer was neutralized with a 5M KOH aqueous solution. The resultant solid was collected and purified with MeOH/ethyl acetate to give the salt as brownish yellow powder (2.23 g, 43%). m.p. > 300 C; 1 H NMR: = 8.39 (d, 6H, J = 20 Hz), 8.77 (d, 6H, J = 20 Hz); 13 C NMR: = 10.76, , , , , ; UV/Vis (methanol): max = 326 nm; elemental analysis calcd (%) for C 23 H 17.2 N 9 O 1.6 K (=C 22 H 12 N 9 K(CH 3 OH)(H 2 O) 0.6 ): C, 57.04; H, 3.58; N, Found: C, 56.66; H, 3.40; N, Synthesis of Co II network of [Co(TPHAP ) 2 (CH 3 OH) 2 (H 2 O)] 3C 6 H 5 NO 2 HNO 3 5H 2 O (TPHAP-Co Kin ): The single crystals were grown from a double-layered solution consisting of a methanol solution of Co(NO 3 ) 2 6H 2 O (131.5 mm) as the top layer, and a nitrobenzene/methanol solution (volume ratio: nitrobenzene:methanol = 7:1) of K + TPHAP (12.8 mm) as the bottom layer at 14 C. After 1 day, pale red crystals were grown. As keeping more than 2 days or giving a shock can cause the transformation to TPHAP-Co Therm -1, all crystals are collected at this moment. The isolated yield was 21% yield (based on the amount of K + TPHAP ). This low yield comes from the high reactivity of TPHAP-Co Kin. Elemental analysis calcd (%) for C 64 H 60 N 22 O 17 Co(=(C 22 H 12 N 9 ) 2 (Co)(CH 3 OH) 2 (C 6 H 5 NO 2 ) 3 (HNO 3 )(H 2 O) 6 ): C, 52.35; H, 4.12; N, Found: C, 52.18; H, 3.83; N, Synthesis of single crystal of [Co(NO 3 )(TPHAP )(CH 3 OH) 2 ] CH 3 OH C 6 H 5 NO 2 2HNO 3 H 2 O (TPHAP-Co Therm -1): The single crystals of (TPHAP-Co Therm -1) were prepared by the structural transformation of a kinetic crystal of [Co(TPHAP ) 2 (CH 3 OH) 2 (H 2 O)] 3C 6 H 5 NO 2 HNO 3 5H 2 O, just leaving the crystallization tube for more than two days. The isolated yield is 31% (calculated based on the amount of K + TPHAP ). Elemental analysis calcd (%) for C 31 H 21 N 13 O 15 Co (= (C 22 H 12 N 9 )(Co)(CH 3 OH) 3 (C 6 H 5 NO 2 )(NO 3 )(HNO 3 ) 2 (H 2 O)): C, 42.09; H, 3.53; N, Found: C, 42.22; H, 3.64; N, Synthesis of single crystal of [Co(NO 3 )(TPHAP )(CH 3 OH)] CH 3 OH 2.5(C 6 H 5 NO 2 ) H 2 O (TPHAP-Co Therm -2): The single crystals were grown from a double-layered solution consisting of a methanol solution of Co(NO 3 ) 2 6H 2 O (131.5 mm) as the top layer, and a nitrobenzene/methanol solution (volume ratio: nitrobenzene:methanol = 7:1) of K + TPHAP (12.8 mm) as the bottom layer at 25 C. After 1 day, dark red crystals were grown and isolated in 3.2% yield. Elemental analysis calcd (%) for C 64 H 60 N 22 O 17 Co(=(C 22 H 12 N 9 )(Co)(CH 3 OH) 2 (C 6 H 5 NO 2 ) 2.5 (NO 3 )(H 2 O)): C, 51.80; H, 3.49; N, Found: C, 51.75; H, 3.31; N, X-ray crystallographic data for K + TPHAP : C 23 H 16 KN 9 O, Mr = , crystal dimensions mm 3, tetragonal, space group P4 2 /n, a = (2), b = (2), c = 9.635(1) Å, V = (6) Å 3, Z = 8, calcd = g cm 3, = 2.94 cm 1, T = 173 C, 6324 unique reflections out of 8203 with I > 2 (I), 359 parameters, 1.38 < < o, final R factors R 1 = and wr 2 = , GOF = S3
4 X-ray Crystallographic data for [Co(TPHAP ) 2 (CH 3 OH) 2 (H 2 O)] 3C 6 H 5 NO 2 HNO 3 5H 2 O (TPHAP-Co Kin ): C H 35 N O Co, M r = , crystal dimensions mm 3, Orthorhombic, space group Pca2 1, a = (5), b = (1), c = (4) Å, V = (2) Å 3, Z = 4, calcd = g cm 3, = 3.28 cm 1, T = 183 C, unique reflections out of with I > 2 (I), 950 parameters, 1.98 < < o, final R factors R 1 = and wr 2 = , GOF = X-ray Crystallographic data for [Co(NO 3 )(TPHAP )(CH 3 OH) 2 ] CH 3 OH C 6 H 5 NO 2 2HNO 3 H 2 O (TPHAP-Co Therm -1): C 54 H 412 N 21 O 13 Co 2, M r = , crystal dimensions mm 3, Orthorhombic, space group Pnc2, a = (3), b = (5), c = (1) Å, V = (1) Å 3, Z = 2, calcd = g cm 3, = 5.76 cm 1, T = 183 C, 9066 unique reflections out of with I > 2 (I), 481 parameters, 1.98 < < o, final R factors R 1 = and wr 2 = , GOF = X-ray Crystallographic data for [Co(NO 3 )(TPHAP )(CH 3 OH)] CH 3 OH 2.5(C 6 H 5 NO 2 ) H 2 O (TPHAP-Co Therm -2): C H 24 N O Co, M r = , crystal dimensions mm 3, monoclinic, space group P2 1 /n, a = (3), b = (3), c = (3) Å, V = (1) Å 3, Z = 4, calcd = g cm 3, = 4.96 cm 1, T = 183 C, 7919 unique reflections out of with I > 2 (I), 891 parameters, 2.45 < < o, final R factors R 1 = and wr 2 = , GOF = CCDC (K + TPHAP ), (TPHAP-Co Kin ), (TPHAP-Co Therm -1) and (TPHAP-Co Therm -2) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via S4
5 Fig. S1 ORTEP view of K + TPHAP CH 3 OH at 50% probability. A methanol molecule is coordinating K + as a crystal solvent. C, H: white, N: blue, O: red, K: purple. Fig. S2 The N HO type hydrogen bonding interactions in a pore of TPHAP-Co Kin. distances are Å (green), Å (blue), (red) Å, (pink) Å, (orange) Å. The N O S5
6 Fig. S3 The N HO type hydrogen bonding interactions in a pore of TPHAP-Co Therm -1. The N O distances are Å (red), Å (sky blue). Fig. S4 AFM images of the surface of single crystal Co-TPHAP Kin : a) immediately after shaking the crystallization tube, b) after 5 min, c) after 10 min. Scan area 10 m 10 m. S6
7 Fig. S5 The bond lengths of HAP skeletons in TPHAP-Co Kin in units of Å. Bidentate TPHAP Monodentate TPHAP C6 N (4) C20 N (4) C28 N (5) C42 N (4) C6 N (4) C20 N (4) C28 N (5) C42 N (4) C12 N (4) C22 N (4) C34 N (5) C44 N (5) C12 N (4) C22 N (4) C34 N (5) C44 N (5) C18 N (4) C19 C (5) C40 N (5) C41 C (4) C18 N (4) C20 C (4) C40 N (5) C42 C (5) C19 N (4) C21 C (4) C41 N (4) C43 C (5) C19 N (4) C41 N (5) Fig. S6 Å. The bond lengths of HAP skeletons in TPHAP-Co Themo -1 and TPHAP-Co Themo -2 in units of TPHAP-Co Themo -1 TPHAP-Co Themo -2 C6 N (4) C20 N (4) C6 N (4) C20 N (3) C6 N (4) C20 N (4) C6 N (3) C20 N (3) C12 N (4) C22 N (4) C12 N (3) C22 N (3) C12 N (4) C22 N (3) C12 N (3) C22 N (3) C18 N (4) C19 C (4) C18 N (3) C19 C (3) C18 N (4) C20 C (4) C18 N (3) C20 C (4) C19 N (4) C21 C (4) C19 N (3) C21 C (3) C19 N (3) C19 N (4) S7
8 Fig. S7 IR spectrum of K + TPHAP. C=N stretching vibration is observed at 1593 cm 1. Fig. S8 The face index of TPHAP-Co Kin crystal and the model picture of the crystal clipping by (0 1 2) (blue) and (0 1 1) (red) plane. S8
9 Fig. S9. The crystal structure of TPHAP-Co Therm -2. a) From a axis with H-bonding interactions. N O distances are Å (black broken line). b) From c axis. Fig. S10. Temperature dependent X-ray diffraction change of TPHAP-Co Therm -1. The powder plots were obtained by integration of CCD 2D-image data. Simulated powder diffraction: dotted line, TPHAP-Co Therm -1; dashed line, TPHAP-Co Therm -2. S9
10 Fig. S11. The simulated void spaces of TPHAP-Co systems using contact surface calculated on Mercury 3.0. TPHAP-Co Kim, 43.0% ( Å 3 ), cavity dimension: 7.4 Å 10.3 Å; TPHAP-Co Therm -1, 30.0% ( Å 3 ), cavity dimension: 4.9 Å 7.4 Å; TPHAP-Co Therm -2, 47.8% ( Å 3 ), cavity dimension: 11.3 Å 2.4 Å. Probe size: 1.2 Å. S10
11 Electronic Supplementary Material (ESI) for Chemical Communications Fig. S12. The CCD 2D-images of TPHAP-CoKin crystals and the capillary pictures before and after in situ study. S11
12 Reference S1) A. P. Hammersley, FIT2D V Reference manual V6.0, Proceedings of the ESRF International Report No. ESRF98HA01T, ESRF, Grenoble, S12
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