Metal-Organic Frameworks for Thin-Layer Chromatographic Applications

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1 Supporting Information for: Metal-Organic Frameworks for Thin-Layer Chromatographic Applications Claudia Schenk, Christel Kutzscher, Franziska Drache, Stella Helten, Irena Senkovska and Stefan Kaskel* Inorganic Chemistry I, Technische Universität Dresden, Bergstr. 66, Dresden, Germany

2 1. General Information All chemicals were used as received without further purification. SEM measurements were done with SU8020 apparatus (HITACHI). The images were taken at 20 thousand fold magnification with an operating voltage of 20 kv and detected by a secondary electrons detector. Nitrogen physisorption experiments were performed at 77 K on BELSORPmax apparatus (MICROTRACBEL, Japan) after activating the samples at least for 12 hours under vacuum (< 10-2 mbar). Powder X-ray diffraction data were collected in transmission geometry on a STOE STADI P diffractometer with Cu Kα1 radiation (λ = Å) at room temperature. The thickness of the coating was estimated by thickness dial gauge F a (KÄFER MESSUHRENFABRIK LTD). AFM measurements were carried out on Dimension D3100 apparatus (DIGITAL INSTRUMENTS). Image evaluation and representation was done using image manipulation software Gwyddion [1]. 2. Structure of DUT 67 DUT-67 contains eight connected [Zr 6 O 4 (OH) 4 ] 12+ cluster and 2,5-thiophene-dicarboxylate (tdc 2- ) as linker. It is a cubic network with octahedral and two different cuboctahedral pores (Figure S1). a) b) Figure S1. Structure of DUR-67: a) [Zr 6 O 4 (OH) 4 ] 12+ cluster with eight tdc 2- linkers; b) network with octahedral (yellow) and cuboctahedral (red) pores. S2

3 3. Composition of stationary phase To produce mechanically stable and homogenously coated TLC plates, suitable additives and binders were evaluated providing a good mechanical stability and adhesion of the material on the aluminium substrate. Chemically inertness as well as minimal effects on separation and detection methods are important properties of the used binders. On the one hand different derivatives of cellulose, e.g. carboxymethyl cellulose, ethyl cellulose, and hydroxypropyl cellulose were used. On the other hand organic polymeric binders, e.g. polyvinylidenfluoride, polyethylenterephthalate, styrene-butadiene-rubber, and gypsum were tested. Hydroxypropyl cellulose (HPC) and the styrene-butadiene-rubber (SBR) turned out to be appropriate binders for DUT wt.% of HPC and 2.1 wt.% of SBR was enough to get mechanically stable layers with sufficient surface area and pore volume and without influencing the crystalline structure of DUT-67. Fluorescent indicator, also frequently used in commercial silica based TLC plates, F 254 (Mn-doped Zn-silicate) was added. The addition of indicator allows to detect compounds absorbing UV-light at 254 nm. Addition of 32 wt.% of F 254 was required to produce homogeneous fluorescent layers without influencing the crystallinity of DUT-67. Smaller amounts led to weak and inhomogeneous fluorescence and to irreproducible analysis. The influence of different ratios of F 254 on the crystallinity and porosity of the composite materials was investigated by PXRD and N 2 physisorption (77 K) measurements. Up to 32 wt.% F 254 no significant influence on the crystallinity of DUT-67 was observed. Higher amount leads to crystallinity loss (Figure S2). As expected, the porosity of the composite decreases gradually with the increasing content of nonporous F 254 (Figure S2). S3

4 a) b) Figure S2. PXRD patterns (a) and nitrogen physisorption isotherms at 77 K (b) of composites containing different amounts of fluorescent indicator F 254. S4

5 4. TLC plates fabrication First, the aluminium sheets (5 cm x 10 cm, 0.3 mm thick) were carefully cleaned with acetone to remove grease. The slurry of all components in ethanol was homogenized in a vibration ball mill for 10 minutes. Typical composition of the slurry was: 0.6 g of DUT-67, 13 mg of hydroxypropyl cellulose (HPC), 19.5 mg of styrene-butadiene-rubber (SBR) (130 mg of 15 wt.% solution in water), 0.3 g of F 254, and 3 ml ethanol. Subsequently, the slurry was spread on an aluminium plate using a CX-1 motorized film applicator (slurry coater, MTV MESSTECHNIK Co.). The plates were dried in air, activated by heating at 80 C in oven for 30 min, and stored under argon atmosphere. The thickness of the coating was 125 µm in average. Figure S3. AFM image of DUT-67 based TLC plate. 5. Thin layer chromatography A capillary with a diameter of 0.6 mm was used to spot analytes. The analytes were spotted three times. The TLC plates were developed in a 3 x 8 cm rectangular shaped glass chamber containing 8 ml of mobile phase. The mobile phase was allowed to equilibrate for 5-10 min prior to development. The optimized mobile phase for benzaldehyde and trans-cinnamaldehyde contained benzene and acetic acid S5

6 (20:1), and for 4-aminophenol and 2-aminotoluene separation - acetonitrile/water/acetic acid (1:1:4). All TLC plates were developed until the mobile phase reached at least a migration distance of 45 mm. After development, TLC plates were dried at room temperature, and analytes are visualized via staining reagents (2,4-dinitrophenylhydrazine for benzaldehyde and trans-cinnamaldehyde, vanillin/sulphuric acid for 4-aminophenol and 2-aminotoluene). A digital photograph was obtained for each separation using a Canon EOS 700D digital camera. 6. Powder X-ray diffraction To verify the stability of the composite in several organic solvents, which are often used in TLC, the PXRD patterns of composite soaked for 1 h in the corresponding solvent: dichloromethane, ethyl acetate, iso-hexane, n-butanol, diethyl ether, water, ethanol, acetone, hydrochloric acid, acetic acid, acetonitrile, benzene were collected (Figure S4). a) S6

7 b) c) Figure S4. PXRD patterns of DUT-67 composite soaked in corresponding solvent for 1 h. (a) diethylether, water, ethanol and acetone; (b) dichloromethane, ethylacetate, iso-hexane and n-butanol; (c) hydrochloric acid, acetic acid, acetonitrile, and benzene. S7

8 The stability of the composite towards eluent mixtures used for the separation (benzene/acetic acid (20:1) and acetonitrile/water/acetic acid (1:1:4)) was also controlled by PXRD (Figure S5). Figure S5. PXRD patterns of DUT-67 based composite after separation. References: [1] (access: 21 November 2016) S8

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