Dataset Information

Synthesis of Highly Gas-Permeable Polyimides of Intrinsic Microporosity Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene.

ABSTRACT: A simple synthetic route to a novel sterically hindered triptycene-based diamine, 1,3,6,8-tetramethyl-2,7-diaminotriptycene (TMDAT), and its use in the preparation of high molecular weight polyimides of intrinsic microporosity (PIM-PIs) are reported. The organosoluble TMDAT-derived polyimides displayed high Brunauer-Emmett-Teller surface areas ranging between 610 and 850 m2 g-1 and demonstrated excellent thermal stability of up to 510 °C. Introduction of the rigid three-dimensional paddlewheel triptycene framework and the tetramethyl-induced restriction of the imide bond rotation resulted in highly permeable polyimides with moderate gas-pair selectivity. The best performing polyimide made from TMDAT and a triptycene-based dianhydride showed gas transport properties located between the 2008 and 2015 polymer permeability/selectivity trade-off curves with H2 and O2 permeabilities of 2858 and 575 barrer combined with H2/N2 and O2/N2 selectivities of 24 and 4.8, respectively, after 200 days of physical aging.

SUBMITTER: Ghanem BS

PROVIDER: S-EPMC6645085 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Highly Gas-Permeable Polyimides of Intrinsic Microporosity Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene.

Ghanem Bader S BS Alghunaimi Fahd F Wang Yingge Y Genduso Giuseppe G Pinnau Ingo I

ACS omega 20180925 9

A simple synthetic route to a novel sterically hindered triptycene-based diamine, 1,3,6,8-tetramethyl-2,7-diaminotriptycene (TMDAT), and its use in the preparation of high molecular weight polyimides of intrinsic microporosity (PIM-PIs) are reported. The organosoluble TMDAT-derived polyimides displayed high Brunauer-Emmett-Teller surface areas ranging between 610 and 850 m<sup>2</sup> g<sup>-1</sup> and demonstrated excellent thermal stability of up to 510 °C. Introduction of the rigid three-dim ...[more]

PMID: 31459273

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Project description:The synthesis of polymers of intrinsic microporosity (PIM) modified with azide groups, the cross linkage by nitrene reaction and their performance as gas separation membranes are reported. The azide modification of the spirobisindane units in the polymer backbone was done by post functionalization of methylated spirobisindane containing polymers. These polymers differ in distribution and concentration of the azide group containing spirobisindane units by applying perfectly alternating and randomly distributed copolymers along the polymer chains. To investigate the influence of concentration of the azide groups, additionally the homopolymer of methylated spirobisindane was synthesized and subjected to identical treatments and characterizations as both copolymers. Cross linkage by nitrene reaction was examined by different temperature treatments at 150, 200, 250 and 300 °C. Characterization of the new polymers was performed by NMR, SEC and FT-IR. Furthermore, the crosslinking process was investigated by means of solid state NMR, TGA-FTIR, DSC and isoconversional kinetic analysis performed with TGA. Gas permeability of CO2, N2, CH4, H2 and O2 was determined by time lag experiments and ideal selectivities for several gas pairs were calculated. The two azide groups per repeating unit degrade during thermal treatments by release of nitrogen and form mechanically stable PIM networks, leading to an increase in gas permeability while selectivity remained nearly constant. Measured diffusivity and solubility coefficients revealed differences in the formation of free volume elements depending on distribution and concentration of the azide groups. Aging studies over about five months were performed and physical aging rates (?P) were evaluated with regard to the concentration and distribution of curable azide functionalities. Subsequently, the enhanced sieving effect during aging resulted in membrane materials that surpassed the Robeson upper bound in selected gas pairs.

Dataset Information

Synthesis of Highly Gas-Permeable Polyimides of Intrinsic Microporosity Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene.

Publications

Synthesis of Highly Gas-Permeable Polyimides of Intrinsic Microporosity Derived from 1,3,6,8-Tetramethyl-2,7-diaminotriptycene.

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