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1 Supporting Information Highly Selective Carbon Dioxide Sorption in an Organic Molecular Porous Material Hyunuk Kim, Yonghwi Kim, Minyoung Yoon, Soyoung Lim, Se Min Park, Gon Seo, Kimoon Kim*, National Creative Research Initiative Center for Smart Supramolecules, Department of Chemistry, and Division of Advanced Materials Science, Pohang University of Science and Technology, San 31 Hyojadong, Pohang , Republic of Korea, School of Applied Chemical Engineering and The Research Institute for Catalysis, Chonnam National University, 300, Yongbong-dong, Gwangju , Republic of Korea General: All the reagents and solvents were purchased from commercial sources and used without further purification. The single-crystal X-ray diffraction data of CO 2 adsorbed 1 were collected on a ADSC Quantum 210 CCD diffractometer with synchrotron radiation at Pohang Accelerator Laboratory. The X-ray powder diffraction patterns were recorded on a Bruker D8 Advance system equipped with a Cu sealed tube (λ= Å). Gas sorption isotherms were volumetrically recorded on a Quantachrome Autosorb 1MP and Bel Japan Belsorp-Max. Gravimetric CO 2 uptake at high pressure, RT was measured with a Robotherm MSB instrument. High purity gases (CO 2 : %, Deokyang Energen, CO: %, Air Liquide, and CH 4 : %, Quadren Cryogenic Processing) were used for the measurements. S1
2 Figure S3. Powder XRD profiles confirming the chemical stability of 1 (a) exposed to moisture in open-air, (b) soaked in MeOH, (c) 0.1 M HCl, (d) benzene, and (e) DMSO Gas Sorption. Gas (CO 2, CH 4 and CO) sorption isotherms for 1 were measured up to 1 bar at 298 K, and 298 K by the Autosorb 1MP instrument. Gravimetric CO 2 uptake at high pressure, RT was measured with a Robotherm MSB instrument. The buoyancies at elevated pressures were corrected by multiplying the skeleton volume of 1 and gas density at each pressure. S2
3 Figure S4. Gas sorption isotherms for 1 at 273 K (red: CO 2, blue: CH 4, black: CO, close marks: adsorption, open marks: desorption). Figure S5. CO 2 sorption isotherms for 1 at 298 K measured up to 30 bar. Table S1. CO 2 uptake and enthalpy of adsorption for MOFs and 1. Asterisks indicate the simulated enthalpy of adsorption due to the lack of experimental data. S3
4 Isosteric heat of CO 2 adsorption The CO 2 sorption data for 1 measured up to 1 bar at 273 K and 298 K were fitted by the virial equation (1) to estimate the enthalpy of adsorption (Figure S1). where p is pressure, n is amount adsorbed, T is temperature, and a 0, a 1, a 2 and b 1 are temperature independent empirical parameters. The isosteric heat of adsorption was estimated from the following equation(2) as a function of CO 2 uptake. ln(p) = ln(n) + 1 T (a + a n + a n2 ) + b Q st = -R (a 0 + a 1 n + a 2 n 2 ) (1) (2) Henry s constant (K H ) is calculated from where T is temperature. (3) The Henry s Law selectivity (S ij ) for gas i over j at 298 K is calculated from the following equation (4) (4) Figure S6. Virial analysis of the CO 2 sorption data for 1 (circles: 298 K, squares: 273 K). a 0 = , a 1 = , a 2 = , a 3 = , b 0 = , b 1 = S4
5 Figure S7. Virial analysis of the CO sorption data for 1 (circles: 298 K, squares: 273 K). a 0 = , a 1 = , a 2 = , a 3 = , b 0 = , b 1 = Figure S8. Virial analysis of the CH 4 sorption data for 1 (circles: 298 K, squares: 273 K). a 0 = , a 1 = , a 2 = , a 3 = , a 4 = , a 5 = , b 0 = , b 1 = In situ IR spectroscopy In situ IR spectroscopic studies were carried out using an FT-IR spectrophotometer (Bio-Rad, FTS 175C) equipped with an in situ cell (GRASEBY SPECAC). A series of FT-IR spectra of CO 2 adsorbed 1 were taken with a thin wafer of each sample on a sample holder while evacuating it with a stepwise increase of temperature from 50 ºC to 150 ºC (Figure S7) Temperature ( o C) Wavenumber (cm -1 ) Figure S9. In situ FT-IR spectra of CO 2 adsorbed 1 recorded during the evacuation with increasing temperature for 50 o C from 150 o C. S5
6 Figure S10. Heat of CO 2 adsorption for 1 estimated by the virial equation X-ray Crystallography: A single-crystal of activated 1 was placed in a thick-wall glass capillary, which was then evacuated, filled with CO 2 gas and sealed while immersed in a liquid nitrogen bath. The diffraction data of CO 2 adsorbed CB[6] were collected at 90 K on a ADSC Quantum 210 CCD diffractometer with synchrotron radiation (λ= Å) at Macromolecular Crystallography 6B1, Pohang Accelerator Laboratory (PAL), Pohang, Korea. The raw data were processed and scaled using the program HKL2000. The structure was solved by direct methods, and the refinements were carried out with full-matrix leastsquares on F 2 with appropriate softwares implemented in SHELXTL program package. X-ray data for CB[6] 3.72CO 2 : C39.72H36N24O19.44, M = , trigonal, R-3 (No. 148), a = (5) Å, c = (3) Å, V =10836(3) Å 3, Z = 9, T = 90 K, µ(synchrotron) = mm -1, ρ calc = g cm -3, reflections measured, 3939 unique (R int = ), R 1 = , wr 1 = for 3146 reflections (I > 2σ(I)), R 1 = , wr 2 = (all data), GOF = 1.094, 735 parameters and 168 restraints. All the non-hydrogen atoms were refined anisotropically. Hydrogen atoms were added to their geometrically ideal positions. Figure S11. X-ray crystal structure of CO 2 adsorbed 1 at site A. The CO 2 molecules adsorbed on sorption sites A, near the wall of the 1D channels, interact with CB[6] through hydrogen bonding (CH O=C=O; Å on average). The occupancies of CB[6] disordered over two positions are 0.57 and The occupancy of CO 2 molecules in site A is S6
7 Figure S12. X-ray crystal structure of CO 2 adsorbed 1 at site A and B. The CO 2 molecules occupying sites B interact with those in sites A in a T-shaped arrangement (O 2 C O 2 C; 3.00 Å). Figure S13. X-ray crystal structure of CO 2 adsorbed 1 at site C. Two CO 2 molecules are included in the CB[6] cavity (site C, 0.89 occupancy) with a slipped-parallel configuration. Reference 1. Yazaydin, A. Ö; Snurr, R. Q.; Park, T.-H.; Koh, K.; Liu, J.; Levan, M. D.; Benin, A. I.; Jakubczak, P.; Lanuza, M.; Galloway, D. B.; Low, J. J.; Wills, R. R. J. Am. Chem. Soc. 2009, 131, S. R.; Wong-Foy, A. G.; Matzger, A. J. J. Am. Chem. Soc. 2008, 130, S7
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