Soluble, microporous, Tröger's Base copolyimides with tunable membrane performance for gas separation

Zhuang, Yongbing; Seong, Jong Geun; Seong, Yu; Lee, Won Hee; Lee, Moonjoo; Cui, Zhaoliang; Lozano, Ángel E.; Guiver, Michael D.; Lee, Young Moo

doi:10.1039/c5cc09783e

Cited by 77 publications

(35 citation statements)

References 34 publications

(37 reference statements)

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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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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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“…By measuring the volumetric flow rate, Q i [cm 3 s À1 ], of the penetrant gas i,t he gas permeability, P i [Barrer],w as calculated according to Equation (2):…”

Section: Characterization Methodsmentioning

confidence: 99%

“…The widespread use of gas‐separation processes in the chemical, petrochemical, and petroleum industries has motivated the search for more efficient gas‐separation processes. Among alternatives to conventional gas‐separation processes, polymeric membrane processes are promising, as they have lower operating and capital costs and are more environmentally friendly …”

Section: Introductionmentioning

confidence: 99%

“…Amonga lternatives to conventionalg as-separation processes, polymeric membrane processes are promising,a st hey have lower operating and capital costs and are more environmentally friendly. [1][2][3][4][5] In addition to possessing excellentc hemical, mechanical, and thermals tability, polyimides (PIs) and polyetherimides have excellent solubility in many solvents, rendering them suitable for membrane preparation. [6][7][8][9] Theh igh selectivity and low permeability of common PIs are due to their low free volume( 10-20%), [10] as explained by Robeson's upper bound [11] and Freeman's theory.…”

Section: Introductionmentioning

confidence: 99%

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A New Pentiptycene‐Based Dianhydride and Its High‐Free‐Volume Polymer for Carbon Dioxide Removal

et al. 2018

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In addition to possessing excellent chemical, mechanical, and thermal stability, polyimides and polyetherimides have excellent solubility in many solvents, which renders them suitable for membrane preparation. Two new monomers [a pentiptycene-based dianhydride (PPDAn) and a pentiptycene imide-containing diamine (PPImDA)] and a pentiptycene-based polyimide [PPImDA-4,4'-hexafluoroisopropylidene diphthalic anhydride (PPImDA-6FDA)] have been synthesized and characterized by FTIR and H NMR spectroscopy, gel-permeation chromatography, mass spectrometry, X-ray photoelectron spectroscopy, thermogravimetric analysis, differential scanning calorimetry, BET surface area, and X-ray diffraction. High-molecular-weight PPImDA-6FDA has remarkable thermal stability and excellent solubility in common organic solvents. It also has an extraordinarily high fractional free volume (0.233) owing to the presence of -C(CF ) - units, the rigid diamine, and the pentiptycene moiety in the polymer structure. It has high CO permeability (812 Barrer) owing to poor chain packing, which is caused by the fact that its rigid groups veil the influence of the ethereal oxygen groups in its backbone. It has the highest CO permeability among all reported pentiptycene-containing polymers (about six times higher than that of the most permeable one) without sacrificing selectivity. The high free volume, good microporosity, high solubility in many solvents, and remarkable thermal stability of PPImDA-6FDA point to the great potential of this polymer for CO removal.

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“…Jin et al . and Zhuang et al . integrated rigid and contorted Tröger's base–based diamines into polyimides backbone and also prepared high performance gas separation polyimide membranes.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Gas Separation Properties of Spirobichroman‐Based Polyimides

Zhang

2018

Macro Chemistry & Physics

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Polymers with rigid and contorted structures are always preferred for use as gas separation membranes. Owing to the contorted nature of the spiro‐center, the spirobichroman structure is an effective scaffold for impeding polymer chain packing. Two spirobichroman‐based diamines, 6,6′‐bis(4‐amino‐2‐trifluoromethylphenoxy)‐4,4,4′,4′,7,7′‐hexamethyl‐2,2′‐spirobichroman (FSBC) and 6,6′‐bis(4‐aminophenoxy)‐4,4,4′,4′,7,7′‐hexamethyl‐2,2′‐spirobichroman (SBC), with or without CF3 side groups are prepared. The two diamines are separately reacted with 3,3′,4,4′‐benzophenonetetracarboxylic dianhydride (BTDA) and 3,3′,4,4′‐diphenylsulfonetetracarboxylic dianhydride (DSDA) to obtain four spirobichroman‐based polyimides, denoted as BTDA‐FSBC, BTDA‐SBC, DSDA‐FSBC, and DSDA‐SBC. The different molecular structures among the four monomers are expected to alter the fractional free volume of the corresponding polyimides by impacting chain‐packing conditions, and then controlling the gas transport properties. Chemical structures, thermal and physical properties of the polyimides are fully characterized. Two different methods, molecular dynamics simulation and Bondi's group contribution method are employed to characterize the fractional free volumes (FFVs) of these polyimides. In the end, it is found that FSBC‐based polyimides exhibit relatively higher gas permeability than SBC‐based polyimides.

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Soluble, microporous, Tröger's Base copolyimides with tunable membrane performance for gas separation

Cited by 77 publications

References 34 publications

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

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

A New Pentiptycene‐Based Dianhydride and Its High‐Free‐Volume Polymer for Carbon Dioxide Removal

Preparation and Gas Separation Properties of Spirobichroman‐Based Polyimides

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