Electronic Supplementary Information
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- Αίγλη Φιλιππίδης
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1 Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Construction of two heteropore covalent organic frameworks with Kagome lattices Yuan Tian, a,b Shun-Qi Xu, b Rong-Ran Liang, b Cheng Qian, a,b Guo-Fang Jiang a, * and Xin Zhao b,* a State Key Lab of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, China. gfjiang@hnu.edu.cn. b CAS Key Laboratory of Synthetic and Self-assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai China. xzhao@sioc.ac.cn. Table of Contents Instruments and Methods Synthesis of the COFs..3-4 Fig. S1-2 FT-IR Spectra of the COFs Fig. S3-4 Solid-state CP/MAS NMR 13 C Spectra the COFs Fig. S5 TGA traces of the COFs Fig. S6 SEM images of the COFs Fig. S7 BET plots of the COFs Fig. S8 CO 2 adsorption isotherms of the COFs Table S1 Elemental analyses of the COFs Table S2-3 Fractional atomic coordinates
2 Instruments and Methods Fourier transform infrared spectroscopy(ft-ir) Fourier transform infrared spectroscopy (FT-IR) was carried out with a Nicolet 380 FT-IR spectrometer. The samples for IR study were prepared as KBr pellets. Solid-state 13 C spectroscopy The 13 C CP/MAS NMR spectra of the dual-pore COFs were recorded on Agilgent DD2 600 Solid NMR System with 4 mm zirconia rotors. The spinning rate is 9 k Hz and the contact time is 3 ms. Thermal gravimetric analysis (TGA) Thermal gravimetric analysis was carried out on THA Q500 by heating the samples from 30 to 950 o C under nitrogen atmosphere at a heating rate of 10 o C/min. Field-emission scanning electron microscopy (FE-SEM) Field-emission scanning electron microscopy (FE-SEM) was performed on a JEOL model JSM-6390LV instrument. Powder X-ray diffraction Powder X-ray diffraction measurements were carried out with an X Pert PROX system using monochromated Cu/K α (λ=0.1542nm). The sample was spread on the square recess of XRD sample holder as a thin layer. Nitrogen adsorption-desorption isotherm measurement The measurements were carried out using a Quadrasorb SI MP. Before gas adsorption measurements, the as-prepared sample (ca. 50 mg) was activated by being immersed in anhydrous dioxane for 12 h. The solvent was decanted and the sample was dried 2
3 under dynamic vacuum at 150 o C for 8 h. The resulting sample was then used for gas adsorption measurements from 0 to 1 atm at 77 K. The Brunauer-Emmett-Teller (BET) method was utilized to calculate the specific areas. By using the non-local density function theory model, the pore size distribution curves were derived from the sorption data. Structural simulation and power X-ray diffraction analysis The Pawley refinements were performed by the Reflux module in the Materials Studio 7.0. Before the simulations, the structures were firstly optimized in Gaussian 09 package by semiempirical calculations at PM3 level. The simulations of the two possible structures were carried out in Accelrys Materials Studio 7.0 software package. The stimulated PXRD patterns were determined by the Refled module. And the unit cell was optimized by Forcite module under molecular mechanics calculation using COMPASS II as the forcefield to give the relative total energies. P1 space group was used for the initial simulations. Procedure for the synthesis of the COFs COF-BTA-DAB. A mixture of 1,1'-biphenyl]-3,3',5,5'-tetracarbaldehyde (BTA) 1 (39.9 mg, 0.15 mmol) and 1,4-diaminobenzene (DAB) (32.4 mg, 0.3 mmol) in a mesitylene /dimethylacetamide/acoh (6 M, aqueous) (5:5:1 by vol., 2.2 ml) was placed in a glass tube. The mixture was sonicated for 2 minutes and then degassed through three freeze-pump-thaw cycles. After that the tube was sealed under vacuum. The mixture was heated at 120 o C for 3 days without disturbance to yield a yellow solid. After being cooled to room temperature, the solvent was decanted and the solid was washed with anhydrous dioxane for 3 times and acetone twice and then dried under vacuum at 120 o C for 4 h to afford COF-BTA-DAB as a yellow powder (53.0 mg, 86.2%). 3
4 COF-BTA-BZ. A mixture of BTA (26.6 mg, 0.1 mmol) and benzidine (BZ) (36.8 mg 0.2 mmol) in mesitylene/dimethylacetamide/acoh (6 M, aqueous) (5:5:1 by vol., 2.2 ml) in a glass tube. The mixture was sonicated for 2 minutes and then degassed through three freeze-pump-thaw cycles. After that the tube was sealed under vacuum. The mixture was heated at 120 o C for 3 days without disturbance to yield a yellow solid. After being cooled to room temperature, the solvent was decanted and the solid was washed with anhydrous dioxane for 3 times and acetone twice and then dried under vacuum at 120 o C for 4 h to afford COF-BTA-BZ as a yellow powder (47.0 mg, 83.6%). Reference 1 Y. Tian, S.-Q. Xu, Q. Cheng, Z.-F. Pang, G.-F. Jiang and X. Zhao, Chem. Commun., 2016, 52, COF-BTA-DAB BTA 1694 DAB Wavenumber(cm -1 ) Fig. S1 FT-IR spectra of COF-BTA-DAB, BTA and DAB. 4
5 1623 COF-BTA-BZ BTA 1694 BZ Wavenumber(cm -1 ) Figure S2. FT-IR spectra of COF-BTA-BZ, BTA and BZ. Fig. S3 Solid-state CP/MAS 13 C NMR Spectrum of COF-BTA-DAB. 5
6 Weight(%) Weight(%) Fig. S4 Solid-state CP/MAS 13 C NMR spectrum of COF-BTA-BZ. a 100 b Temperature ( o C) Temperature (oc) Fig. S5 TGA traces of (a) COF-BTA-DAB and (b) COF-BTA-BZ. 6
7 Gas uptake (cm 3 g -1 ) Gas uptake (cm 3 g -1 ) 1/[Q(P 0 /P-1))] 1/[Q(P 0 /P-1)] Fig. S6 SEM images of COF-BTA-DAB (left) and COF-BTA-BZ (right). a b Relative Pressure (P/P 0 ) Relative Pressure (P/P 0 ) Fig. S7 BET surface area plots for (a) COF-BTA-DAB and (b) COF-BTA-BZ calculated from their N 2 absorption isotherms. a 70 b Pressure (Bar) Pressure (Bar) Fig. S8 CO 2 adsorption isotherms of (a) COF-BTA-DAB and (b) COF-BTA-BZ at 273 K. Table S1 Elemental analyses of COF-BTA-DAB and COF-BTA-BZ. C (%) H (%) N (%) COF-BTA-DAB Theoretical Found COF-BTA-BZ Theoretical Found
8 Table S2 Fractional atomic coordinates for the unit cell of COF-BTA-DAB with DP-AA stacking. COF-BTA-DAB: Space group symmetry P-6 a = b = Å, c = 3.6 Å α = β = 90, γ = 120 H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C
9 H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C C C C C C C C C C C C C C C C C C C C N C N C N C N C N C N C N C N C N C N C N C N
10 Table S3 Fractional atomic coordinates for the unit cell of COF-BTA-BZ with DP-AA stacking. COF-BTA-BZ: Space group symmetry P-6 a = b = Å, c = 3.6 Å α = β = 90, γ = 120 H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C
11 H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C H C
12 C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C N C N C N C N C N C N C N C N C N C N C N C N
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