Electronic Supplementary Information. Selective Sorption of Light Hydrocarbons on a Family of
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1 Electronic Supplementary Information Selective Sorption of Light Hydrocarbons on a Family of Metal-Organic Frameworks with different Imidazolate Pillars Hong-Ru Fu and Jian Zhang* State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences Fuzhou Fujian P. R. China. * Corresponding Author zhj@fjirsm.ac.cn Fax: Tel:
2 General methods. 1,3,5-(tri-benzoic acid)aniline and 1,3,5-(tri-benzoic acid) phenol) were synthesized via suzuki reaction. 1 Et COOEt COOH O O Br + NH 2 NH 2 NH 2 HO B OH Br Br EtOOC COOEt HOOC COOH A mixture of 2,4,6-Tribromoaniline (2.5 g, 7.5 mmol), p-ethoxycarbonylphenyl boronic acid (6 g, 30.0 mmol), Na 2 CO 3 (4.0 g, 40 mmol), and Pd(PPh 3 ) 4 (0.7 g, 0.5 mmol) was added into degassed toluene methanol water (80/40/40 ml) under an argon atmosphere. The resulting reaction mixture was stirred for 24 h under reflux. After removal of the solvent, the residue was extracted with dichloromethane (80 3 ml), washed with brine (80 ml), dried over anhydrous MgSO 4 and concentrated in vacuum. The residue was purified by silica gel column chromatography (petroleumether/dichloromethane¼1/5) to give 1,3,5-tri(p-methoxycarbonyl-phenyl)aniline (2.56 g, 73%), which was hydrolyzed with 6 M NaOH to afford the title compound. 1H NMR (DMSO-d 6, 400 MHz) d (ppm): (s, 3H), 8.10 (s, 3H), (s, 12H); 13 C NMR (DMSO-d6, 150 MHz) d (ppm): , , , , , , ; FT-IR (KBr, cm1): 3382, 3014, 2660, 2538, 1697, 1608, 1569, 1512, 14 47, 1416, 1393, 1317, 1286, 1241, 1181, 1016, 847, 76 4; MS (ESI) (m/z ) calcd for C27N1H20O6 : 451.1, found: Adsorption Characterization. Virial Equation Analysis. The virial equation can be written as follows: n ln( ) p 2 A0 An 1 A2n (S1) where n is the amount adsorbed (mol g -1 ) at pressure p (Pa). At low surface coverage, the A 2 and higher terms can be neglected and the equation becomes n ln( ) A An 0 1 p (S2)
3 A linear graph of ln(n/p) versus n is obtained at low surface coverage and this is consistent with neglecting higher terms in equation (S2). A 0 quantifies the adsorbate-adsorbent interactions while A 1 is related to adsorbate-adsorbate interactions. This equation has been used extensively in probe molecule studies of adsorption on porous carbons and MOFs. Adsorption Equilibrium Selectivity. The selectivities of C3, C2 over CH 4 were calculated by the ideal adsorption solution theory (IAST). IAST is a method for predicting the adsorption equilibria for components in a mixture using only single-component adsorption data at the same temperature and on the same adsorbent. The measured experimental data is excess loadings (q ex ) of the pure components CO 2, CH 4, C 2 H 4, C 2 H 6 and C 3 H 8 for MOF-ms, which should be converted to absolute loadings (q) firstly. Here Z is the compressibility factor. The Peng-Robinson equation was used to estimate the value of compressibility factor to obtain the absolute loading, while the measure pore volume is also necessary. In order to perform the IAST calculations, the single-component isotherm was fitted by the single-site Langmuir-Freundlich (SSLF) adsorption model to correlate the pure-component equilibrium data and further predict the adsorption of mixtures. The SSLF model is described as: Here p is the pressure of the bulk gas at equilibrium with the adsorbed phase (kpa), q is the adsorbed amount per mass of adsorbent (mol kg -1 ), q m1 are the saturation
4 capacities of sites 1 (mol kg -1 ), b 1 are the affinity coefficients of sites 1 (1/kPa), n 1 are the deviations from an ideal homogeneous surface. To investigate the separation of binary mixtures, the adsorption selectivity is defined by x 1 and x 2 are the absolute component loadings of the adsorbed phase in the mixture. These component loadings are also termed the uptake capacities. We calculate the values of x 1 and x 2 using the Ideal Adsorbed Solution Theory (IAST) of Myers and Prausnitz. 4 Table. S1 The crystallgraphy data. Compound 1-mim 1-eim formula [Zn 2 (NH 2 -BTB)][2-mim] 3 DMF 7H 2 O formula weight crystal system Orthorhombic Monoclinic space group Cmcm C2/c a (Å) (12) (8) b (Å) (17) (12) c (Å) (4) (4) α ( o ) β ( o ) (4) γ ( o ) V (Å 3 ) (5) (3) Z 4 8 Absorption (mm 1 ) coefficient μ(mo/cu Kα) (mm 1 ) F(000) temperature (K) Theta min, max(deg) 2.39, , T min and T max 0.799, , R(int) N ref, N par 7298, , 4965 [Zn 2 (NH 2 -BTB)][2-eim] 3 DMF 5H 2 O R 1,wR [I 2σ(I)] , , S R 1, wr 2 (all data) , ,
5 Table. S2 The crystallgraphy data. Compound 1-pim 1-buim formula [Zn 2 (NH 2 -BTB)][2-pim] 3 DMF 6H 2 O formula weight crystal system Monoclinic Monoclinic space group C2/c C2/c a (Å) (5) (15) b (Å) (8) (3) c (Å) (2) (6) α ( o ) β ( o ) (3) (7) γ ( o ) V (Å 3 ) (2) (6) Z 8 4 Absorption coefficient (mm 1 ) μ(mo/cu Kα) (mm 1 ) F(000) temperature (K) Theta min, max(deg) 5.32, , T min and T max 0.765, , R(int) N ref, N par 8952, , 4405 [Zn 2 (NH 2 -BTB)][2-buim] 3 DMF 5H 2 O R 1,wR [I 2σ(I)] , , S a R 1, wr 2 (all data) , , a R 1 =Σ F o F c / Σ F o. wr 2 ={Σ[w(F o 2 F c 2 ) 2 ]/Σ[w(F o 2 ) 2 ]} 1/2 ; w=1/[σ 2 (F o 2 )+(ap) 2 + bp] Figure S1 a) 3D pillared-layer framework of 1-buim along the a axis; b) 2-fold interpenetrated topology of the framework of 1-ims along the c axis.
6 Figure S2 a) 3D framework of 1-mim along the b axis; b) 3D framework of 1-mim along the b axis; c) 3D framework of 1-buim along the b axis; d) 3D framework of 1-buim along the b axis. Figure S3 a) The single framework of 1-buim along the b axis; b) the other single framework of 1-buim along the b axis; c) the single framework of 1-buim along the c axis d) the ther single framework of 1-buim along the c axis; e) The 2-fold interpenetrated framework along the c axis, the 2-n-butylimidazole was limited on the well of the channel.
7 Figure S4 The pore size distributions of these porous MOFs. Figure S5 a) CO 2 sorption isotherms of MOF-ms at 273 K; b f) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-ims at 273 K, respectively.
8 Figure S6 a) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-mim at 273 K; b) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-mim at 297 K. Figure S7 a) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-eim at 273 K; b) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-eim at 297 K. Figure S8 a) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-pim at 273 K; b) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-pim at 297 K.
9 Figure S9 a) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-buim at 273 K; b) CH 4, C 2 H 2, C 2 H 4, C 2 H 6 and C 3 H 8 sorption isotherms of 1-buim at 297 K. Table S3 Summary of the enthalpies (Q st,n=0 /kj mol 1 ) of gas adsorption on four complex at 273 and 297 K obtained from the virial equation. CH 4 C 2 H 2 C 2 H 4 C 2 H 6 C 3 H 8 CO 2 MOF-mim MOF-eim MOF-pim MOF-buim Table S4 Relevant physical properties of C1 C3 hydrocarbons. Gas σ a b c M P B P μ d (Å) (K) (K) [esu cm] CH α e (10-25 cm3) C 2 H C 2 H C 2 H C 3 H a Kinetic diameter. b Melting point. c Boiling point. d Dipole moment. e Polarizability
10 Figure S10 IAST-predicted adsorption selectivity of C3/C1, C2/C1 on 1-ims at 273 K. a) 1-mim; b) 1-eim;c) 1-pim;d) 1-buim. Figure S11 The Powder XRD patterns of 1-ims.
11 Figure S12 The TGA plots of 1-ims. References 1. He, Y. B.; Bian, Z.; Kang, C. Q.; Cheng, Y. Q.; Gao, L. X.; Tetrahedron, 2010, 66, Fu, H. R.; Wang, F.; Zhang, J. Dalton Trans., 2014, 43, Lin, X.; Telepeni, I.; Blake, A. J.; Dailly, A.; Brown, C. M.; Simmons, J. M.; Zoppi, M.; Walker, G. S.; Thomas, K. M.; Mays, T. J.; Hubberstey, P.; Champness, N. R.; Schröder, M. J. Am. Chem. Soc., 2009, 131, Myers, A. L. Prausnitz, J. M. AIChE J. 1965, 11,
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