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1 The picture can't be displayed. Mihail Barboiu Institut Européen des Membranes - CC 047, Université Montpellier 2 - Place Eugène Bataillon Montpellier - France

2 Tuning the gaz-diffusion through molecular networks in multicomponent functional membranes In general, the gas transport performances are controlled by the gas-diffusivity though glassy polymers and by solubilityselective behaviors of rubbery polymers. The trade-off behaviour high selectivity/low permeability and vice versa is the most important challenge in developing membrane systems with high permeability whilst keeping a reasonable selectivity

3 Polymer blending- molecular additives Polymer blending is a versatile tool to combine the beneficial properties of polymers and molecular additives to increase the free volume of the polymer and the solubility. A. Car, C. Stropnik, W. Yave, K.V. Peinemann, J. Membr. Sci. 307 (2008) A. Car, C. Stropnik, W. Yave, K.V. Peinemann, Sep. Purif. Technol. 62 (2008) S. R. Reijerkerk, M. H. Knoef, K. Nijmeijer, M. Wessling J. Membr. Sci. 352 (2010) 126.

4 Polymers of intrinsic microporosity (PIMs): robust, solutionprocessable, organic nanoporous materials P. M. Budd, B. S. Ghanem, S. Makhseed, N. B. McKeown, K. J. Msayib, C. E. Tattershall Chem. Commun., 2004, P. M. Budd, N. B. McKeown, Polym. Chem., 2010,1, Soluble PIMs may be processed into thin films for use as highly selective gas separation membranes. PIMs = potential heterogeneous catalysis and hydrogen storage systems.

5 Science 2007;318:

6 Are MOF (ZIF) membranes better in gas separation than those made of zeolites? the structural flexibility of MOFs apparently prevents a sharp molecular sieving with a pore size estimated from the rigid crystallographic structure by size exclusion. mixed matrix MOFs membranes which show improved performance in comparison with the pure polymer membranes. Different from zeolites as organic inorganic material, the MOF nanoparticles can be easily embedded into organic polymers, and standard shaping technologies to hollow fibers or spiral wound geometries can be applied Yan-Shuo Li, Fang-Yi Liang, Helge Bux, Armin Feldhoff, Wei-Shen Yang, and Jürgen Caro Angew. Chem. Int. Ed. 2010, 49,

7 Israel J. Chem. 2013, 53(1-2),

8 DYNAMERS Proc. Natl. Acad. Sci. 2004, 101, DYNAMIC POLYMERS generated via REVERSIBLE COVALENT CONNECTIONS OHC CHO H 2 N NH 2 N N dialdehyde diamine polyimines n OHC CHO H 2 N NH O O HN NH 2 N NH O O HN N dialdehyde dihydrazide polyacylhydrazones n courtesy of Jean-Marie LEHN

9 COMPONENT RECOMBINATION between DYNAMIC POLYMER CHAINS + Function: rigidity, complexant + + Dynamic Moieties: Imine Esters, etc Dynamic exchange Lehn, J.-M. Dynamers: dynamic molecular and supramolecular polymers. Prog. Polym. Sci. 2005, 30, Cross-linking

10 Soft-to-Hard Transformation of Dynamers Hard Monomers H N N O A Si O Si O Very Soft Stretchy Film Si O Si H N N O O B Si O Si O Si O C H n C O O H 2 N N O O N H H MeO OHC O D O O CHO OMe A B A B A B A B A A D A B C D C B A D 60, 24h, in CHCl 3 Soft Stretchy Film 25mol% 50mol% 75mol% Conversion of a Soft Stretchy Film into a Hard Tough Film by Dynamic Modification courtesy of Jean-Marie LEHN

11 Core centres Connectors Functional heads Israel J. Chem. 2013, 53(1-2),

12 1. the hydrophobic polythf linear macromonomers have been used to generate the crystalline phases considered as low-permeable for the gas transport; 2) the polyme(peg) star-type macromonomers allowinga high solubility for the CO 2 contribute to the cross-linking behaviour of the dynameric network. 3) The connection between the macromonomeric units is based on thereversible covalent isophthaldiminecore connectors. Israel J. Chem. 2013, 53(1-2),

13 The increase of the free volume is most likely caused by the incorporation of 3, acting as separator of linear PolyTHF compact matrix Israel J. Chem. 2013, 53(1-2),

14 ROFs allow high permeabilities for the CO 2 and interesting CO 2 /light gas selectivities Israel J. Chem. 2013, 53(1-2),

15 Minimizing the size of elastomeric segments would allow to achieve the molecular limit for highly organized domains Solubility Diffusion

16 PolyTHF Triamine T- 440 PolyTHF Triamine T Core center + Core center

17 CH 4 CO 2 % en triamine augmente Fugita Model: P = A P exp (-B/FFV) A D B CH 4 4,60E+04 1,04 CO 2 2,80E+05 1 N 2 1,10E+04 0,96 O 2 2,95E+04 0,94 FVL augmente B CH 4 > B CO 2 > B N 2 > B O 2 Vc CH 4 > Vc CO 2 > Vc N 2 > Vc O 2 H. Fugita, Fortshritte Hochpolymere Forschung, 1961, 3,

18 % en triamine augmente P CO 2 / P N 2 P CO 2 / P CH 4 FVL augmente P O 2 / P N 2 18

19 Double dynameric membranes: supramolecular hard and macromolecular permeable soft domains Membrane P O2 P N2 P CO2 S CO2/N2 Barrer Barrer Barrer P P P P P P S O2/N2 Chem. Commun., 2012, 48,

20 Metallodynameric membranes Chem. Commun., 2012, 48,

21 Gas transport solubility and diffussion 25 6 S CO2 (10-3.cm 3 (STP).cm - 3.cmHg -1 ) ,5 1 1,5 2 Zn(CH 3 COO) 2 content (%) D CO 2 (10-7.cm 2.s -1 ) ,0 0,5 1,0 1,5 2,0 Zn(CH 3 COO) 2 content (%) Increasing S with Zn 2+ content Interaction Zn 2+ --H 2 O - CO 2 Zn 2+ S time-lag 10-3 (cm 3 (STP)cm- 3 cm -1 Hg ) S' 10-3 (cm 3 (STP)cm -3 cm -1 Hg ) g 1 d g 1 d g 1 d g 1 d Even if the process seems to be controlled by CO 2 sorption, the diffusion becomes more influent under decomplexation reaction effect which restricts the diffusion process Good agreement between calculated and experimental solubility coefficient

22 Pure gas permeabilities and b) pure CO 2 /N 2, O 2 /N 2 CO 2 /H 2 selectivities at 298 K and Pa, Chem. Commun., 2012, 48,

23

24 Table 1 Permeation results for single gas at 5 bars Membrane Permeability (Barrer) Selectivity Selectivity N (CO 2 /N 2 ) (CO 2 /CH 4 ) 2 CO 2 CH 4 T T T5 0, , T Table 2 CO 2 and N 2 permeability results mix gas experiments Membrane CO2 Permeability (Barrer) 1,2 bar dry 5 bar dry 1,2 bar wet 5 bar wet T T T T Membrane N2 Permeability (Barrer) 1,2 bar dry 5 bar dry 1,2 bar wet 5 bar wet T T T T Collab. with M. Sandru and M. Britt Hag

25 Robeson graph for 5 bars Robeson graph for 1,2 bars wet Collab. with M. Sandru and M. Britt Hag

26 Collab. with M. Sandru and M. Britt Hag

27

28 Self-healing membranes

29 ROFs and light

30 ROFs and light UV µ = 3D C-C para = 9Å C-C para = 5,5Å Molecular switches- molecular stirrers Before after irradiation Solubility + Free volume +

31 Light controlled gas transport 2N N N H2N N N NH 2 2 N N N MD3 DD3 MT3 P = 3 bar, TA UV ( nm) Time600s P gaz (barrer) % + 78% - 16% +640% +160% + 113% MD3 DD3 MT3 31

32 Rubbery Organic Frameworks Variability, versatility, easy screening for best performances. Diffussion-controlled transport Self healing, stability Adaptability-commutable the rubbery version of MOFs, ZIFs or PIMs

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