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1 Supporting Information Degradation of Paraoxon and the Chemical Warfare Agents VX, Tabun and Soman by the Metal-Organic Frameworks UiO-66- NH 2, MOF-808, NU-1000 and PCN-777. Martijn C. de Koning,* Marco van Grol, Troy Breijaert. TNO, Lange Kleiweg 137, 2288 GJ Rijswijk, The Netherlands. Characterization of MOFs (BET surface areas, particle sizes, SEM images, PXRDs), hydrolysis curves of all MOF/agent/condition combinations & corresponding kinetic plots and selected 31 P- NMR spectra and mass spectra used to identify tabun hydrolysis products (PDF). Contents Synthesis of MOFs MOF Characterization... 2 Degradation profiles of all tested reactions Selected 31 P-NMR-spectra of degradation products of tabun... 8 Selected LC-MS-spectra of degradation products of tabun References Synthesis of MOFs. MOF-808 was synthesized and activated according to literature procedures 1. In short, a mixture of ZrOCl 2.8H 2 O and benzene-1,3,5-tricarboxylic acid in 50/50 DMF/Formic acid was prepared and stored in a 130 o C oven for a period of 48 hours. The resulting precipitate was washed with DMF and solvent exchanged for acetone followed by activation under reduced pressure at 150 o C for a period between hours. PCN-777 was synthesized and activated according to literature procedure 2. PCN-777 was prepared by dissolving ZrOCl 2.8H 2 O and the H 3 TATB linker in DMF followed by the addition of TFA as a modulator. The resulting solution was stored overnight in a 120 o C oven and the precipitate washed with DMF followed by solvent-exchanging for acetone and activation under reduced pressure at 150 o C for a period of 48 hours. UiO-66-NH 2 was synthesized 3 using the commercially available 2-aminoterephthalic acid linker which was dissolved in DMF together with ZrCl 4 and conc. HCl, the resulting solution was stored
2 in a 80 o C oven overnight. The precipitate was solvent-exchanged with ethanol followed by drying in vacuo and activation under reduced pressure (0,05 mbar) at 150 o C for a period of 3 hours. NU-1000 was synthesized according to literature procedures 4. In short, the 1,3,6,8-tetrakis(pbenzoate)pyrene linker was synthesized via a palladium catalysed carbon-carbon coupling (suzuki coupling) of tetrabromopyrene and 4-ethoxycarbonylphenylboronic acid, using a tetrakis(triphenylphosphine)-palladium(0) catalyst, followed by base catalyzed hydrolysis and acidification of the resulting liquid to form a precipitate of the target compound (see scheme S1). Scheme S1. Reaction scheme for the synthesis of H 4 TBAPy linker NU-1000 was synthesized by dissolving ZrOCl 2.8H 2 O, benzoic acid and the linker in DMF, and the resulting solution was stored in a 120 o C oven overnight. The benzoic acid was removed via chemical treatment with aqueous HCl, followed by a solvent exchange with acetone and activation at 120 o C under reduced pressure. MOF Characterization BET surface areas were determined with a Micromeritics ASAP2020 (Table S1). Particle sizes were determined using scanning electron microscopy (SEM), see Figures S1 and S2 & and Table S1. PXRD s of all synthesized MOFs were in agreement with those reported (see Figures S3-S6). Table S1. Experimental and literature Brunauer-Emmett-Teller surface areas of the synthesized metal-organic frameworks and particle sizes determined using SEM. MOF Activation pressure (mbar) Activation temperature ( o C) BET surface area (m 2 g -1 ) Particle size (µm) NU MOF-808 0, ,8-1,2 PCN-777 0, ,0-5,7 UiO-66-NH 2 0,
3 Figure S1. Left: SEM image of PCN-777; right: SEM image of MOF-808. Figure S2. Left: SEM image of UiO-66-NH2; Right: SEM image of NU-1000
4 Figure S3. PXRD spectrum of UiO-66-NH 2 Figure S4. PXRD spectrum of MOF-808
5 Figure S5. PXRD spectrum of PCN-777 Figure S6. PXRD spectrum of NU-1000
6 Degradation profiles of all tested reactions. Figure S7. Hydrolysis of POX in NEM buffer (a) and MQ (c) and the respective plots (b,d) of ln[c] vs time (min), [c] = concentration residual agent (mm) r 2 >0,95. UiO-66-NH 2 ( ), MOF-808 ( ), NU-1000 ( ), PCN-777 ( ), blank ( ). Figure S8. (a) Hydrolysis profile of GD in NEM buffer; (b) Hydrolysis profile of GD in MQ. UiO-66-NH 2 ( ), MOF-808 ( ), NU-1000 ( ), PCN-777 ( ), blank ( ).
7 Figure S9. Hydrolysis of VX in NEM buffer (a) and MQ (c) and the respective plots (b): r 2 >0.98 and (d): r 2 >0.80) of ln[c] vs time (min), [c] = concentration residual agent (mm). UiO-66- NH 2 ( ), MOF-808 ( ), NU-1000 ( ), PCN-777 ( ), blank ( ). conversion (%) Figure S10. Hydrolysis profile of GA in NEM buffer. UiO-66-NH 2 ( ), MOF-808 ( ), NU-1000 ( ), PCN-777 ( ), blank ( ).
8 conversion (%) Tabun in MQ NU-1000 PCN-777 MOF-808 UiO-66-NH 2 Blank GA conversion (%) Tabun in MQ NU-1000 PCN-777 MOF-808 UiO-66-NH Time (min) Time (min) Figure S11. Hydrolysis of GA in MQ and the respective ln[c] vs time plots (r 2 >0.90, except NU- 1000: r 2 >0.80), [c] = concentration residual agent (mm). UiO-66-NH 2 ( ), MOF-808 ( ), NU ( ), PCN-777 ( ), blank ( ). Selected 31 P-NMR-spectra of degradation products of tabun Me 2 N O P OH EtO Figure S12. Reaction mixture of tabun + MOF-808 in MQ showing residual tabun (δ -7.8 ppm), ethylphosphate (δ 0.4 ppm) and dimethylaminophosphoramidic acid monoethylester (δ 3.7 ppm).
9 Me 2 N O P OH EtO Figure S P spectrum of an aliquot of the reaction mixture of Figure S8 diluted in 50 mm NEM buffer (ph 10). Dimethylaminophosphoramidic acid monoethylester shifts to δ 11 ppm, ethylphophoric acid to δ 3.4 ppm. The residual tabun hydrolysed under the basic conditions to the peak at 11 ppm. O P HO EtO CN
10 Figure S P-Spectrum of the reaction mixture of tabun + PCN-777 in MQ shows the formation of phosphorocyanidic acid monoethyl ester (δ -20 ppm) and ethylphosphate (δ 0.4 ppm). Selected LC-MS-spectra of degradation products of tabun
11 Figure S15. A: LC-MS chromatogram of the filtered sample obtained by degradation of tabun by PCN-777 in MQ. B/C: Extracted ion chromatograms of resp. peaks at 3.8 min (phosphorocyanidic acid monoethyl ester) and 1.7 min (ethylphosphate). D: LCMS chromatogram of the blanc sample (water). E/F: Mass spectra of resp. ethylphosphate and
12 phosphorocyanidic acid monoethyl ester. G: MS/MS spectrum of phosphorocyanidic acid monoethyl ester.
13
14 Figure S16. A: LC-MS chromatogram of the blanc sample (water); B: LC-MS chromatogram of the filtered sample obtained by degradation of tabun by NU-1000 in NEM buffer. C: Extracted ion chromatograms of peak at 1.7 min (N-ethylmorpholine). D: Extracted ion chromatograms of peak at 2.5 min (dimethylphosphoramidic acid monoethylester); E: MS/MS spectrum of dimethylphosphoramidic acid monoethylester. References 1. Jiang, J.; Gándara, F.; Zhang, Y.-B.; Na, K.; Yaghi, O. M.; Klemperer, W. G. Superacidity in Sulfated Metal Organic Framework-808 J. Am. Chem. Soc. 2014, 136, Feng, D.; Wang, K.; Su, J.; Liu, T.-F.; Park, J.; Wei, Z.; Bosch, M.; Yakovenko, A.; Zou, X.; Zhou, H.-C. A Highly Stable Zeotype Mesoporous Zirconium Metal-Organic Framework with Ultralarge Pores Angew. Chemie Int. Ed. 2015, 54, Katz, M. J.; Brown, Z. J.; Colón, Y. J.; Siu, P. W.; Scheidt, K. A.; Snurr, R. Q.; Hupp, J. T.; Farha, O. K. A facile synthesis of UiO-66, UiO-67 and their derivatives. Chem. Commun. (Camb). 2013, 49, Wang, T. C.; Vermeulen, N. A.; Kim, I. S.; Martinson, A. B. F.; Stoddart, J. F.; Hupp, J. T.; Farha, O. K. Scalable synthesis and post-modification of a mesoporous metal-organic framework called NU-1000 Nat. Protoc. 2015, 11,
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