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1 Supporting Information An n-channel Two-Dimensional Covalent Organic Framework Xuesong Ding, Long Chen, Yoshihito Honsho, Xiao Feng, Oraphan Saengsawang, Jingdong Guo, Akinori Saeki, Shu Seki,* Stephan Irle, Shigeru Nagase, Vudhichai Parasuk, and Donglin Jiang* Corresponding Author: Professor Donglin Jiang Department of Materials Molecular Science, Institute for Molecular Science, National Institutes of Natural Sciences, 5-1 Higashiyama, Myodaiji, Okazaki , Japan. Tel./Fax: Professor Shu Seki Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka , Japan Section A. Materials and methods Section B. Synthetic procedures Section C. FT-IR spectral profiles Section D. Simulation of Tetragons Section E. Atomic coordinates of unit cell Section F. Simulation and calculation of layer structure Section G. Double exponential curve fitting of FP-TRMC profiles Section H. Supporting reference S1
2 Section A. Materials and methods Anhydrous N, N-dimethylacetamide (DMAc, 99.0%) and o-dichlorobenzene were purchased from Kanto Chemicals. Methanol, anhydrous acetone (99.5%), anhydrous 1,4-dioxane (99.0%), toluene, bis(pinacolato)diboron, potassium acetate, and anhydrous dichloromethane (99.0%) were purchased from Wako Chemicals. Mesitylene, 4,7-dibromo-2,1,3-benzothiadiazole, and boron tribromide were purchased from TCI. (1,1-Bis(diphenylphosphino)ferrocene)dichloropalladium(II) and anhydrous N,N-dimethylformamide (DMF, 99.8%) were purchased from Aldrich. 1 H NMR spectra were recorded on JEOL models JNM-LA400 NMR spectrometers, where chemical shifts (δ in ppm) were determined with a residual proton of the solvent as standard. Fourier transform Infrared (FT-IR) spectra were recorded on a JASCO model FT-IR-6100 infrared spectrometer. UV-Vis-IR diffuse reflectance spectrum (Kubelka-Munk spectrum) was recorded on a JASCO model V-670 spectrometer equipped with integration sphere model IJN-727. Matrix-assisted laser desorption ionization time-of-flight mass (MALDI-TOF MS) spectra were recorded on an Applied Biosystems BioSpectrometry model Voyager-DE-STR spectrometer in reflector or linear mode. Field-emission scanning electron microscopy (FE-SEM) was performed on a JEOL model JSM-6700 operating at an accelerating voltage of 5.0 kv. The sample was prepared by drop-casting an acetone suspension onto mica substrate and then coated with gold. High-resolution transmission electron microscopy (HR-TEM) images were obtained on a JEOL model JEM-3200 microscopy. The sample was prepared by drop-casting an acetone suspension of NiPc-COF onto a copper grid. X-ray diffraction (XRD) data were recorded on a Rigaku model RINT Ultima III diffractometer by depositing powder on glass substrate, from 2θ = 1.5 up to 60 with 0.02 increment. Nitrogen sorption isotherms were measured at 77 K with a Bel Japan Inc. model BELSORP-mini II analyzer. Before measurement, the samples were degassed in S2
3 vacuum at 200 C for more than 10 h. The Brunauer-Emmett-Teller (BET) method was utilized to calculate the specific surface areas. By using the non-local density functional theory (NLDFT) model, the pore volume was derived from the sorption curve. All calculations were carried out using Gaussian 03 program. S1 The tetragonal pores were simulated with hybrid density functional theory at the B3LYP level using a double-zeta basis set (Lanl2dz) effective core potential (Lanl2 ECP) for Ni atoms and the 3-21G (d) basis set for all other atoms using Gaussian 03 program, S2 and single point calculations with basis set Lanl2dz for Ni atom and 6-31G(d) for the other atoms to improve energies. Molecular modeling and Pawley refinement were carried out using Reflex, a software package for crystal determination from XRD pattern, implemented in MS modeling ver 4.4 (Accelrys Inc.). S3 Unit cell dimension was first manually determined from the observed XRD peak positions using the coordinates. We performed Pawley refinement to optimize the lattice parameters iteratively until the R WP value converges. The pseudo-voigt profile function was used for whole profile fitting and Berrar-Baldinozzi function was used for asymmetry correction during the refinement processes. The final R WP and R P values were and 9.18%, respectively. The density-functional tight-binding (DFTB) method including Lennard-Jones (LJ) dispersion was applied to calculate the molecular and electronic structures of stacking types of the two dimensional 2D-NiPc-BTDA COF with D 2h space group. The corresponding LJ and crystal stacking energies as well as the HOMO-LUMO energy gaps were computed. The calculations were carried out with the DFTB+ program package version 1.1. S4 DFTB is an approximate density functional theory method based on the tight binding approach and utilizes an optimized minimal LCAO Slater-type all-valence basis set in combination with a two-center approximation for Hamiltonian matrix elements. The Coulombic interaction between partial atomic charges was determined using the self-consistent charge (SCC) S3
4 formalism. Lennard-Jones type dispersion was employed in all calculations to describe van der Waals (vdw) and π stacking interactions. Where possible, DFTB parameters from the dftb.org website S5 were employed as follows. Standard DFTB parameters for X Y element pairs (X, Y = C, H, O, S, and N) interactions were selected from the mio-0-1 set as well as B X (X = C, O, and N) related parameters were taken from the matsci-0-3 set. Note that, the DFTB parameters for B O element pairs were used instead of one for B S without result perturbation. Moreover, the B H parameters were replaced by C H from the same matsci-0-3 set to avoid the misleading bond between B and H atoms. The results with replaced parameters were validated, subsequently, utilized for all calculations with periodic boundary conditions (PBC). The parameters for Ni X (X = C, H, O, S and N) were taken from the trans3d-0-1 set. The optimal single layer 2D model systems consisted of 332 atoms with lattice constant of a = b = Å, then, the 4 types of stacking forms such as perfect AA, slipped structures with slight shifts by 0.72 and 1.44 Å in a and b directions as well as AB form were generated. For each type of stacking form, the structures were modeled by manually applying 0.1 Å intervals in separate geometry optimizations close to their optimum values. S4
5 Section B. Synthetic procedures 4,5-dimethoxyphthalodinitrile was prepared from veratrole using a literature procedure. S6 (2,3,9,10,16,17,23,24-Octahydroxyphthalocyaninato)nickel(II) ([OH] 8 NiPc) was synthesized according to reported method. S7 (2,3,9,10,16,17,23,24-Octahydroxyphthalocyaninato)nickel(II) ([OH] 8 NiPc). (MeO) 8 NiPc (142.0 mg, mmol) was suspended in 10 ml of dichloromethane, and boron tribromide (0.68 ml, 7 mmol) was added under N 2 atmosphere. The mixture was stirred for 3 days, and 10 ml of methanol was added slowly. The solvent was removed, the residue was washed by methanol and centrifuged. After repeating the cycle of wash and centrifuge more than 3 times, the precipitate was collected and dried in vacuum, to give (OH) 8 NiPc as a dark green solid in 70% yield. MALDI-TOF MS for C 32 H 16 N 8 O 8 Ni (Calc ), found m/z = ([M] + ). 2,1,3-Benzothiadiazole-4,7-bis(pinacolato)diboronic ester. A mixture of 4,7-dibromo-2,1,3-benzothiadiazole (1.009 g, 3.44 mmol), bis(pinacolato)diboron (1.919 g, 7.56 mmol), potassium acetate (2.023 g, mmol) in 1,4-dioxane (20 ml) was throughly degassed by three cycles of freeze-pump-thaw. (1,1-Bis(diphenylphosphino)ferrocene) dichloropalladium(ii) was added under Ar stream, the mixture was further degassed twice. Then the reaction mixture was heated up to reflux for 12 h. The reaction mixture was cooled to room temperature, added with water (30 ml), and extracted with EtOAc (50 ml 3), the combined organic layer was washed with brine and dried over anhydrous Na 2 SO 4, evaporated to dryness, the residue was purified by column chromatography using hexane/etoac (4/1) as an eluent. The first fraction was collected, evaporated and dried under vacuum, to afford a light yellow solid (0.586 g, 43% yield). 1 H NMR (CDCl 3, 400 MHz): δ (ppm) 8.13 (s, 2H), S5
6 1.44 (s, 24H). 13 C NMR (CDCl 3, 100 MHz): δ (ppm) , , 84.41, MALDI-TOF MS: m/z calcd for C 18 H 26 B 2 N 2 O 4 S, ; found, ([M] + ). 2,1,3-Benzothiadiazole-4,7-diboronic acid (BTDADA). A mixture of 2,1,3-benzothiadiazole-4,7- bis(pinacolato)diboronic ester ( g, 1.25 mmol) and sodium periodate (1.605 g, 7.5 mmol) in THF (16 ml) and water (4 ml) was stirred under Ar at r.t. for 30 min. Hydrochloric acid (1.0 M, 2.0 ml) was added dropwise to the above mixture, stirred under Ar for 24 h. The mixture was evaporated and the resulted microcrystal was collected by filtration, thoroughly washed with water, hexane and diethyl ether, to afford a light yellow fine crystalline soild (260 mg, 93% yield). 1 H NMR (d 6 -THF, 400 MHz): δ (ppm) 8.16 (s, 2H), 7.72(s, 2H). 13 C NMR (d 6 -THF, 100 MHz): δ (ppm) , MALDI-TOF MS: m/z calcd for C 6 H 6 B 2 N 2 O 4 S, ; found, ([M] + ). 2D-NiPc-BTDA COF. The mixture of [OH] 8 NiPc (21 mg, 0.03 mmol) and 1,4-benzothiadiazole diboronic acid (BTDADA, 13.6 mg, 0.06 mmol) in o-dichlorobenzene /DMAc (2 ml, 1/2 in vol.) were degassed in Pyrex tube (10 ml) by three freeze-pump-thaw cycles. The tube was sealed off and heated at 120 C for 7 days. The precipitate was collected by centrifugation, washed with anhydrous acetone for 5 times, extracted by Soxhlet with anhydrous acetone for 3 days, and dried at 150 C under vacuum for 24 h, to give a dark green powder in 85% isolation yield from a 2/1 stoichiometric ratio of BDBA and [OH] 8 NiPc. Elemental analysis (%) calcd. for (C 44 H 8 B 4 N 12 O 12 S 2 Ni) n (theoretical formula for an infinite 2D COF) C (52.70), H (1.21), N (16.76), found C (48.58), H (2.02), N (16.66). S6
7 Section C. FT-IR spectral profiles 250 2D-NiPc-BTDA COF [OH] 8 PcNi 100 BTDADA Wavenumber (cm -1 ) Figure S1. FT-IR spectra of [OH] 8 PcNi, BTDADA, and 2D-NiPc-BTDA COF. Table S1. Peak assignments for FT-IR spectrum of 2D-NiPc-BTDA COF (A), [OH] 8 PcNi (B), and BTDADA (C). A B C Assignment and Notes (cm 1 ) (cm 1 ) (cm 1 ) C=C vibration of phenyl ring C=N stretch of Pc macrocycles C=C vibration of phenyl ring B O stretch, characteristic band of boroxoine compounds C O stretch B C stretch, characteristic band of boroxoine compounds Vibration and characteristic band of Pc macrocycles N S stretch Vibration and characteristic band of Pc macrocycles Out-of-plane bending of the C H bonds of phenyl rings S7
8 Section D. Simulation of tetragons Tetragons with different orientation of BTDA groups Method: OPT: B3LYP//Lanl2dz <Ni> /3-21G(d) <the others> Single point calculation: B3LYP//Lanl2dz<Ni>/ 6-31G(d) <the others> Case 1: D 4h kcal/mol 776 (B2U)- - O , ev 777 (B2U)- - V , ev Case 2: D 4h 0.0 kcal/mol 776 (B2U)- - O , ev 777 (A2U)- - V , ev Case 3: C s kcal/mol 776 (A")- - O , ev 777 (A")- - V , ev Case 4: C 2v kcal/mol 776 (B1)- - O , ev 777 (B1)- - V , ev Case 5: C 2v kcal/mol 776 (B1)- - O , ev 777 (B1)- - V , ev Case 6: D 2h kcal/mol (lowest) 776 (B3U)- - O , ev 777 (B3U)- - V , ev Figure S2. Simulation of tetragons with different BTDA orientations. Case 6 D 2h is the most stable structure among the six geometries. S8
9 Section E. Atomic coordinates of unit cell Table S2. Fractional atomic coordinates for the optimized tetragonal pore structure No. Atom x y z 1 N Ni N C C C C C C C C O B O N C N C C C C C C C C C C N O B C C C C S9
10 35 C C O Ni H H H H H H N N S C C C C H Ni N N C N C O B O C C C C C C C O B C C S10
11 73 C C C C O H H H H H N N S Table S3. Crystal system Space group Refined crystal data Unit cell dimensions Tetragonal D 4h P4 a = b = Å c = Å α = 90, β = 90, γ = 90 Pseudo-Voigt of peak profile function U = , V = , W = Rietveld asymmetry correction P = Pawley refinement R wp = 11.82% R p = 9.18% S11
12 Section F. Simulation and calculation of structure Table S4. The total DFTB energies, Lennard-Jones contributions (LJ), and the crystal stacking energies per monolayer as well as the corresponding HOMO-LUMO energy gap. Stacking Distance [Å] Total DFTB Energy [Hartree] LJ Energy [Hartree] LJ Crystal Stacking Energy [kcal mol -1 ] Crystal Stacking Energy [kcal mol -1 ] HOMO- LUMO gap [ev] Monolayer Perfect AA AA Slipped 3.4 at 1.44 Å AA Slipped 3.4 at 0.72 Å Perfect AB Figure S3. Plots of relative energies vs. stacking distance for AA and AB stacking modes. S12
13 Section G. Double exponential curve fitting of FP-TRMC profiles Figure S4. Double exponential curve fitting (red) of FP-TRMC profiles (blue), using m 1 exp[ m 2 (t Δt)] + m 3 exp[ m 4 (t Δt)]. Table S5. Parameters of double exponential curve fitting of FP-TRMC profiles, using m 1 exp[ m 2 (t Δt)] + m 3 exp[ m 4 (t Δt)]. The m 2 component is the fast and m 4 is the slow component, respectively. ΦΣµ = m 1 exp[ m 2 (t 1.1E-6)] + m 3 exp[ m 4 (t 1.1E-6)] value error m E E-11 m E m E E-11 m χ E-16 NA R NA Ar S13
14 ΦΣµ = m 1 exp[ m 2 (t 1.1E-6)] + m 3 exp[ m 4 (t 1.1E-6)] SF 6 ΦΣµ = m 1 exp[ m 2 (t 1.1E-6)] + m 3 exp[ m 4 (t 1.1E-6)] value error Anneal SF 6 1h m E E-11 m E m E e-11 m χ E-16 NA R NA ΦΣµ = m 1 exp[ m 2 (t 1.1E-6)] + m 3 exp[ m 4 (t 1.1E-6)] value value error m E E-11 m E m E E-11 m χ E-16 NA R NA error m E E-11 m E m E E-11 m χ E-16 NA R NA Anneal SF 6 24h ΦΣµ = m 1 exp[ m 2 (t 1.1E-6)] + m 3 exp[ m 4 (t 1.1E-6)] Anneal O 2 24h value error m E E-11 m E m E E-12 m χ E-16 NA R NA S14
15 Section G. Supporting references S1. Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Wallingford CT, S2. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299. S3. Accelrys, Material Studio Release Notes, Release 4.4, Accelrys Software, San Diego S4. Aradi B.; Hourahine B.; Frauenheim T. J. Phys. Chem. A, 2007, 111, S5. S6. Metz, J.; Schneider, O.; Hanack, M. Inorg. Chem. 1984, 23, S7. Michael, R. M.; Lawrence, A. M.; Noll, B. C.; Pierpont, C. G. Inorg. Chem. 1998, 37, S15
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