A novel intrinsically microporous ladder polymer and copolymers derived from 1,1′,2,2′-tetrahydroxy-tetraphenylethylene for membrane-based gas separation

Ma, Xiaohua; Pinnau, Ingo

doi:10.1039/c5py01796c

Cited by 56 publications

(36 citation statements)

References 45 publications

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“…Pinnau and coworkers designed several PIM-based copolymers of TPE (tetraphenylethylene) and PIM-1, 187 as well as copolymers of PIM-6FDA-OH and 6FDA-DABA (PIM-6FDA-OH-co-6FDA-DABA). 193 Interestingly, the latter copolymers with a SBIDA to DABA ratio of 80/20 showed a remarkable ~50% enhancement in the BET surface area from PIM-6FDA-OH (300 m 2 g -1 compared to 190 m 2 g -1 ).…”

Section: Copolymers and Blending Of Polymersmentioning

confidence: 99%

Gas Permeation Properties, Physical Aging, and Its Mitigation in High Free Volume Glassy Polymers

et al. 2018

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Hundreds of polymers have been evaluated as membrane materials for gas separations, but fewer than 10 have made it into current commercial applications, mainly due to the effects of physical aging and plasticization. Efforts to overcome these two problems are a significant focus in gas separation membrane research, in conjunction with improving membrane separation performance to surpass the Robeson upper bounds of selectivity versus permeability for commercially important gas pairs. While there has been extensive research, ranging from manipulating the chemistry of existing polymers (e.g., thermally rearranged or cross-linked polyimides) to synthesizing new polymers such as polymers of intrinsic microporosity (PIMs), there have been three major oversights that this review addresses: (1) the need to compare the approaches to achieving the best performance in order to identify their effectiveness in improving gas transport properties and in mitigating aging, (2) a common standardized aging protocol that allows rapid determination of the success (or not) of these approaches, and (3) standard techniques that can be used to characterize aging and plasticization across all studies to enable them to be robustly and equally compared. In this review, we also provide our perspectives on a few key aspects of research related to high free volume polymer membranes: (1) the importance of Robeson plots for membrane aging studies, (2) eliminating thermal history, (3) measurement and reporting of gas permeability and aging rate, (4) aging and storing conditions, and (5) promising approaches to mitigate aging.

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Section: Copolymers and Blending Of Polymersmentioning

confidence: 99%

Gas Permeation Properties, Physical Aging, and Its Mitigation in High Free Volume Glassy Polymers

et al. 2018

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“…PIM-1 is a widely studied candidate in the class of PIMs due to its rigid and contorted structure. 9 Since then, several examples of PIMs containing units such as triptycene, 10,11 spirobisindane, 12,13 Tr€ oger's base, [14][15][16][17] spirobischromane, 18 spirobifluorene, 19 hexaphenylbenzene, 20 naphthalene, 21 tetraphenylethylene, 22 phthalimide, 23 tribenzotriquinacene, 24 cardo PIMs, and so on 25 have been synthesized and evaluated as membrane materials for gas separation.…”

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confidence: 99%

Synthesis, characterization, and gas permeation properties of adamantane‐containing polymers of intrinsic microporosity

Shrimant

Shaligram

Kharul

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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A new bis(catechol) monomer, namely, 4,4 0 -((1r,3r)-adamantane-2,2-diyl)bis(benzene-1,2diol) (THADM) was synthesized by condensation of 2-adamantanone with veratrole followed by demethylation of the formed (1r,3r)-2,2-bis(3,4 dimethoxyphenyl)adamantane. Polycondensation of THADM and various compositions of THADM and 5,5,6 0 ,6 0 -tetrahydroxy-3,3,3 0 ,3 0 -tetramethylspirobisindane was performed with 2,3,5,6-tetrafluoroterephthalonitrile (TFTPN) to obtain the homopolymer and copolymers. These polymers demonstrated good solubility in common organic solvents such as dichloromethane, chloroform, and tetrahydrofuran and could be cast into tough films from their chloroform solutions. GPC analysis revealed that number average molecular weights of polymers were in the range 48,100-61,700 g mol 21 , suggesting the formation of reasonably high molecular weight polymers. They possessed intrinsic microporosity with Brunauer-Emmett-Teller (BET) surface area in the range 703-741 m 2 g 21 . Thermogravimetric analysis of polymers indicated that 10% weight loss temperature was in the range 513-518 8C demonstrating their excellent thermal stability. THADM-based polymer of intrinsic microporosity (PIM) showed P(CO 2 ) 5 1080, P(O 2 ) 5 232 and appreciable selectivity [a(CO 2 /CH 4 ) 5 22.6, a(CO 2 /N 2 ) 5 26.7, and a(O 2 /N 2 )5 5.7]. The gas permeability measurements revealed that with increase in the content of adamantane units in PIMs, selectivity increased and permeability decreased, following the trade-off relationship. The gas separation properties of PIMs containing adamantane units were located close to 2008 Robeson upper bound for gas pairs such as CO

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“…More work has been done to explore the applicability of microporous organic membranes in H 2 separations . According to Figure , many membranes (such as TPIM‐1, KAUST‐PI‐1 (KAUST : King Abdullah University of Science and Technology, PI : polyimide), PIM‐Trip‐TB, and PIM‐EA‐TB) exhibit excellent hydrogen separation performances with data points above the trade‐off line, which can be explained by the good balance between small pores and high surface areas of these membranes.…”

Section: Gas Separation With Microporous Organic Membranesmentioning

confidence: 99%

Microporous Organic Materials for Membrane‐Based Gas Separation

2017

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Membrane materials with excellent selectivity and high permeability are crucial to efficient membrane gas separation. Microporous organic materials have evolved as an alternative candidate for fabricating membranes due to their inherent attributes, such as permanent porosity, high surface area, and good processability. Herein, a unique pore-chemistry concept for the designed synthesis of microporous organic membranes, with an emphasis on the relationship between pore structures and membrane performances, is introduced. The latest advances in microporous organic materials for potential membrane application in gas separation of H , CO , O , and other industrially relevant gases are summarized. Representative examples of the recent progress in highly selective and permeable membranes are highlighted with some fundamental analyses from pore characteristics, followed by a brief perspective on future research directions.

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A novel intrinsically microporous ladder polymer and copolymers derived from 1,1′,2,2′-tetrahydroxy-tetraphenylethylene for membrane-based gas separation

Abstract: A novel intrinsically microporous polymer was synthesized by polycondensation reaction of 1,1′,2,2′-tetrahydroxy-tetraphenylethylene (TPE) and 2,3,5,6-tetrafluoroterephthalonitrile (TFTPN).

Cited by 56 publications

References 45 publications

Gas Permeation Properties, Physical Aging, and Its Mitigation in High Free Volume Glassy Polymers

Gas Permeation Properties, Physical Aging, and Its Mitigation in High Free Volume Glassy Polymers

Synthesis, characterization, and gas permeation properties of adamantane‐containing polymers of intrinsic microporosity

Microporous Organic Materials for Membrane‐Based Gas Separation

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