Iron and porphyrin metal organic frameworks: insight into
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1 Iron and porphyrin metal organic frameworks: insight into structural diversity, stability and porosity Alexandra Fateeva*,a,e, Jade Clarisse a, Guillaume Pilet a, Jean-Marc Grenèche b, Farid Nouar c, Brian K. Abeykoon a, Frederic Guegan a, Christelle Goutaudier a, Dominique Luneau a, John E. Warren d,e, Matthew J. Rosseinsky e and Thomas Devic c a b c d e Université de Lyon, Université Claude Bernard Lyon 1, Laboratoire des Multimatériaux et Interfaces, UMR CNRS 5615, 43 Bd du 11 Nov 1918, Villeurbanne, France Institut des Molécules et des Matériaux du Mans, UMR CNRS 6283 Université du Maine - Avenue Olivier Messiaen Le Mans, France Institut Lavoisier, UMR CNRS 8180, Université de Versailles Saint-Quentin-en-Yvelines, 45 avenue des Etats- Unis, Versailles cedex, France School of Materials, The University of Manchester, Manchester M13 9PL, UK Department of Chemistry, University of Liverpool, Liverpool, L697ZD, UK 1
2 Single crystal diffraction Crystal data of complexes 1, 2, 4 A and 4 B were collected at room temperature using a Geminini Oxford Diffractometer (MoKα radiation, l = Å) equipped with a CCD camera and by using the related software 1. An absorption correction (analytical) has been applied to all the data sets 2. All the structures were solved by direct methods using the SIR97 program 3 combined with Fourier Difference and the refined against F using the CRYSTALS program 4. In each structure, all atomic displacements for non-hydrogen atoms were refined using an anisotropic model. Hydrogen atoms have been placed by Fourier Difference account the hybridization of the supporting atoms and for the possible presence of hydrogen bonds in the case of donor atoms. Hydrogen atoms have been finally refined using a riding mode. During 4 A crystal structure refinement, C14 and C15 carbon atoms of the pyrazin ring were refined as 50% of occupancies due to geometry symmetrical elements of the space group. During 4 B crystal structure refinement, C1 carbon atom of the pyrazin ring was refined as 50% of occupancy due to geometry symmetrical elements of the space group. CCDC , , and references contain the supplementary crystallographic data for complexes 1, 2, 4 A and 4 B, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via Table 1. Single-crystal X-ray diffraction data collection details and structure refinement results A 4 B Empirical formula C 51 H 34 Cs 1 Fe 2 N 5 O 11 C 68 H 40 Fe 3 N 8 O 8 C 56 H 32 Fe 3 N 8 O 8 C 52 H 30 Fe 3 N 6 O 10 Formula weight (g.mol -1 ) Temperature (K) Z Wavelength (Å) Crystal system Monoclinic Tetragonal Tetragonal Orthorhombic Space group C2/c I4/mmm I4/mmm Cmmm Unit-cell dimensions a = (5) a = (9) Å (7) a = 6.835(2) b = (2) b = (9) Å (7) b = (4) c = (2) c = (3) Å (1) c = (2) β = (6) β = 90 β = 90 β = 90 Volume (Å 3 ) (6) (9) (5) 3737(1) Density (calculated) Absorption coefficient (mm -1 ) F(000) Crystal size (mm 3 ) Crystal color Green Dark Dark Dark Crystal shape Plate Cubic Needle Plate Reflections collected / unique [R int ] 18836/6671 [0.039] 11249/2413 [0.064] 6805/1577 [0.070] 6623/2554 [0.098] Absorption correction Analytical Analytical Analytical Analytical Data / restraints / parameters 4408/20/ /35/99 887/6/ /8/112 Goodness of fit Final R/R w indices / / / / Δρ max / Δρ min (e -.Å -3 ) 2.39/ / / /-1.40 Explanations about IUCRcheckcif alerts levels A and B Alerts level A (2, 4 A and 4 B ) Structure Contains Solvent Accessible VOIDS of : this is usually encountered for porous MOF structures and has not then been corrected. Alerts level B 2
3 2, 4 A and 4 B Calculated Density less than 1.0 g.cm -3 : this is due to 3D porous networks of MOF architectures and has not then been corrected. 1 and 4 B D-H Without Acceptor : even using special commands of CRYSTALS program (refinement) and Fourier Difference, it has not been possible to find hydrogen atoms for these oxygen atoms creating some hydrogen interactions with other acceptors atoms. Powder X-Ray diffraction Powder X Ray diffraction was performed on a PANanlytical XpertPro MRD diffractometer with a Cu Kα 1 radiation (λ = Å) used with 40 kv and 30mA settings in / mode, reflection geometry. Due to a strong preferential orientation, the powder diffraction data of (4 B ) were measured at room temperature on a Bruker D8 Advance diffractometer with a Debye-Scherrer geometry, in the 2θ ranges 5-40 (unless stated otherwise). The D8 system is equipped with a Ge(111) monochromator producing Cu Kα 1 radiation (λ = Å) and a LynxEye detector Position [ 2Theta] Fig S1. PXRD pattern of sample (1) (black) and the calculated powder pattern from the single-crystal structure (blue) Position [ 2Theta] Fig S2. PXRD pattern of 2, 5 minutes after removal of the solvent (black), 35 minutes after the removal of the solvent (grey) and the calculated powder pattern from the single-crystal structure (blue) 3
4 Fig S3. PXRD pattern of Position [ 2Theta] Fig S4. PXRD pattern of 4 B after synthesis (black), after BET (purple) and the calculated powder pattern from the single-crystal structure (blue) Variable temperature diffraction Variable temperature diffraction was performed using a θ-θ Bruker-D8 Advance diffractometer equipped with a HTK-1200N (Anton Parr) high temperature chamber and a LYNXEYE XE detector (Cu radiation). Diagrams were collected every 10 C between 20 and 300 C. The peak at 2 = 25.7 corresponds to the alumina sample holder. 4
5 Thermogravimetric Analysis (TGA) 2-Theta - Scale Fig S5. Variable temperature PXRD of compound 1 Thermogravimetric analysis (TGA) was performed with a TGA/DSC 1 STARe System from Mettler Toledo. Around 6 mg of sample is heated at a rate of 10 K min -1 from 25 to 800 C, in a 70 µl alumina crucible, under air atmosphere (20 ml.min -1 ). Fig S6. TG analysis of 1 5
6 Fig S7. TG analysis of 2 Fig S8. TG analysis of 3 6
7 Fig S9. TG analysis of 4 B Supercritical CO 2 drying (SCD) The as-synthesized solid contained DMF in the pores hence liquid solvent exchange was performed with anhydrous ethanol during 5 cycles. In each cycle the solid was soaked in anhydrous ethanol for 24 hours, then centrifuged and the solvent was replaced. The solid containing ethanol was then activated using a supercritical CO 2 dryer to prevent pores collapse due to capillary effect. About 40 mg of ethanol exchanged sample was loaded into a glass cell in the chamber. The chamber was then filled with liquid CO 2 and after 5 cycles of purge (5min) and soak (1H) steps, the temperature was elevated to obtain a supercritical CO 2 fluid. After 90 minutes, the bleed valve was slightly opened to allow a slow pressure decrease. When the pressure was low enough, the purge valve was opened and the chamber opened. The sample was finally loaded into a sorption cell. Gas Sorption Measurements Surface areas were measured by N 2 adsorption and desorption at 77.3 K using a Micromeritics ASAP 2010 volumetric adsorption analyzer for compounds (1), (3), (4 B ) and a BelsorpII mini BEL apparatus for compound (2) which was activated by SCD.The samples (40-50 mg) were activated under secondary vacuum at 150 C prior to sorption measurement. The BET surface calculations was performed using points at the pressure range 0 <P/P 0 <
8 Fig S10. N 2 sorption isotherm for compound 3, BET surface area: 440m 2 g -1 Fig S11. successive N 2 sorption isotherms for compound 4 B ) showing no noticeable porosity loss after sorption and reactivation process 8
9 Scanning Electron Microscopy The morphology of crystalline materials was observed by scanning electron microscopy on FEI Quanta 250 FEG microscope in the microscopy centre of Lyon1 University. Samples were mounted on stainless pads and sputtered with 2 nm of a Au/Pd mixture to prevent charging during observation. Fig S12. SEM images of 1 Fig S13. SEM picture of 2 9
10 Fig S14. SEM pictures of 3 Fig S15. SEM pictures of compound 4 B Infrared Spectroscopy Infrared spectroscopy was performed with a Nicolet 380 FT-IR spectrometer coupled with the Attenuated Total Reflectance (ATR) accessory 10
11 Intensity (a.u.) Intensity (a.u.) wavenumber (cm-1) Fig S16. IR spectrum of wave number (cm -1 ) Fig S17. IR spectrum of (2) Because of the air sensitivity of compound 2 the IR spectrum was recorded without intensively drying the compound, therefore bands corresponding to ethanol are present 11
12 Intensity (a.u.) Intensity (a.u.) wave number (cm-1) Fig S18. IR spectrum of compound wave number (cm -1 ) Fig S19. IR spectrum of compound 4 B In all the above spectra, the peaks at 1600 and 1390 cm -1 attest of the antisymmetric and symmetric stretching of the carboxylate C=O respectively, the peak at 1580 cm -1 is due to the presence of porphyrin aromatic C=C, the large band at 1330 cm -1 is characteristic of C=N stretch in aromatic porphyrin or the aromatic base for compound 2 and 4 B. 12
13 Water stability tests To test water stability samples of compound 1 and 4 B (40 mg) were immersed in 3 ml of water and allowed to stand for 24 hours. After that time the remaining solids were filtered and dried. Powder X- ray diffraction and IR spectra were collected. Comparison of the supernatant color for compounds 1 and 4 B Fig S20. supernatant form water stability test of 1 (left) and 4 B right Position [ 2Theta] Fig S21. PXRD pattern of 1 as synthesized sample (black) and after 24 hours in water (blue) 13
14 Intensity (a.u.) wave number (cm -1 ) Fig S22. IR spectra of 1 as synthesized (black) and after 24 hours in water (blue) The appearance of the peak at 1700cm -1 attests of the presence of uncoordinated carboxylic acid, from some extent of hydrolysis of the carboxylate-iron bond in compound Position [ 2Theta] Fig S23. PXRD pattern of 4 B as synthesised sample (black) and after 24 hours in water (blue) (PXRD obtained in reflection geometry) 14
15 Intensity (a.u.) wave number (cm-1) Fig S24. IR spectra of 4 B before (black) and after 24 hours in water (blue) Mossbauer spectroscopy The 57 Fe Mossbauer spectrum was recorded at 300 K and 77K in a transmission geometry using a 57 Co/Rh source mounted on an electromagnetic drive with a triangular velocity form and a bath cryosytat. 15
16 References (1) CrysAlisPro, version (rel , CrysAlis171.NET), Oxford Diffraction Ltd. (2) O. D. L. CrysAlisPro, version (rel , CrysAlis1 171.NET), (compiled Aug. 27, 2010, 11:50:40). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by: R. C. Clark, J. S. Reid, Acta Crystallogr., Sect. A 1995, 51, (3) G. Cascarano, A. Altomare, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, D. Siliqi, M. C. Burla, G. Polidori, M. Camalli, Acta Crystallogr., Sect. A 1996, A52. (4) D. J. Watkin, C. K. Prout, J. R. Carruthers, P. W. Betteridge, Chemical Crystallography Laboratory, Oxford, (5) J. Cosier and A. M. Glazer, J. App.Cryst., 1986, 19, (6) J. E. Warren, FMD: Free My Data - an automated frame conversion program utilising Simon Parson's Eclipse and Bruker Frm2Frm executables. (2010) (7) APEX2 (Bruker AXS Inc. 2009) (8) SAINT Version 7.68A (Bruker AXS Inc., 2009) (9) SADABS 2008/2 (Sheldrick, 2008) (10) O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst., 2009, 42, (11) SHELXL, G.M. Sheldrick, Acta Cryst., 2008, A64, (12) R. E. Thorne, Z. Stum, J. Kmetko, K. O Neill, and R. Gillilan, J. App. Cryst., 2003, 36,
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