Synthesis and characterization of novel triptycene dianhydrides and polyimides of intrinsic microporosity based on 3,3ʹ-dimethylnaphthidine

Ghanem, Bader S.; Alghunaimi, Fahd; Ma, Xiaohua; Alaslai, Nasser Y.; Pinnau, Ingo

doi:10.1016/j.polymer.2016.08.075

Cited by 50 publications

(44 citation statements)

References 36 publications

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“… a) Transport properties of PPImDA‐6FDA and the existing pentiptycene‐based membranes against the 2008 CO 2 /CH 4 Robeson upper bound; b) transport properties of PPImDA‐6FDA and the existing pentiptycene‐based membranes against the 2008 CO 2 /N 2 Robeson upper bound; c) transport properties of pentiptycene‐ and triptycene‐based PI membranes against the 2008 Robeson CO 2 /CH 4 upper bound; d) transport properties of pentiptycene‐ and triptycene‐based PI membranes against the 2008 CO 2 /N 2 Robeson upper bound …”

Section: Introductionsupporting

confidence: 59%

“…The structures of the monomers and polymers were confirmed by 1 HNMR spectroscopy (500 MHz) by using aV arian Unity Inova NMR systems spectrometer with [D]chloroform or [D 6 ]DMSO as the solvent and tetramethylsilane (TMS) as the standard. To identify the functional groups of the synthesized monomers and polymers, ATR-FTIR spectroscopy was conducted by using aS pectrum One ATR-FTIR spectrometer (PerkinElmer) with 16 scans and aresolution [29,32,35,37,50,[56][57][58] ChemSusChem 2018, 11,472 -482 www.chemsuschem.org of 4cm À1 .AS ciex API3000 triple quadrupole mass spectrometer equipped with both ESI and APCI sources was used to confirm the chemical formulas and molecular weights of the monomers. Ag elpermeation chromatograph [Shimadzu with aC BM-20A system controller,L C-20AD solvent delivery unit, and RID-10A differential refractive index (RI) detector] was utilized to measure the numberaverage and weight-average molecular weights (denoted by M n and M w ,r espectively) of the polymers by using THF or DMAc as the mobile phase and polystyrene as the standard.…”

Section: Characterization Methodsmentioning

confidence: 99%

“…[29] Substituting the isopropyl chain with al inear alkyl chain in KAUST-PI-1' leads to performance below that of PPImDA-6FDA. The presence of 6FDA and two ethereal oxygen atoms reduces the effect of the pentiptycene moiety.A lso, (TDA1)-DMN [58] (TDA1 = 9,10-dimethyl-2,3,6,7-triptycene tetracarboxylic dianhydride (TDA1), DMN = 3,3'-dimethylnaphthidine) with triptycene-based dianhydrides containing dimethyl bridgehead groups and DMN exhibited performance above the 2008 CO 2 /CH 4 Robesonu pper bound owing to the high rigidity of the dianhydride (it has no dioxane ring) and the diamine.…”

Section: Gas-permeation Testsmentioning

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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Section: Introductionsupporting

confidence: 59%

Section: Characterization Methodsmentioning

confidence: 99%

Section: Gas-permeation Testsmentioning

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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“…To date, extensive studies have been implemented to create high porosities in microporous polymers in order to attain highly permeable membranes (e.g., polyimides) for separating O 2 from N 2 ( Figure ) . The designed syntheses of O 2 ‐selective microporous organic membranes via structure–property optimization will be the next focus.…”

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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“…[1][2][3][4][5][6] Triptycene and pentiptycene molecules are members of the iptycene family, with the former being the simplest member bearing three phenyl rings connected via a [2.2.2] bicyclic ring. Materials bearing the iptycene motif demonstrate desirable properties such as good organosolubility, 5,7,8 high intrinsic microporosity, [9][10][11][12] high thermal stability, 13 improved photostability, 14 enhanced fluorescence quantum yields 15,16 and others. [17][18][19][20][21][22] Consequently, such polymers (derived from iptycene monomers) have found application in the design of gas separation membranes, 23,24 organic photovoltaic devices, 25,26 liquid crystals, 27-29 . molecular sensors (for explosives derived from nitroaromatics) 30,31 and molecular machinery.…”

Section: Introductionmentioning

confidence: 99%

Triptycene‐based fluorescent polymers with pendant alkyl chains: interaction with fullerenes and morphology of thin films

Ansari

Mallik

Mondal

et al. 2018

Polymer International

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We report unique triptycene‐based alternating copolymers bearing long alkyl chains as pendants. Syntheses utilized 2,6‐diethynyltriptycene and appropriate alkyloxyarene monomers polymerized via Sonogashira cross‐coupling reaction to yield triptycene‐based poly(phenylene ethynylene)s. Resulting polymers are soluble in organic solvents and were characterized using various techniques. Experimental results suggest the polymers are thermally stable and fluorescent. The fluorescence emission is quenched in the presence of fullerenes (C60 and C70) suggesting strong host–guest interactions. The magnitude of the binding constant between the polymers and these fullerenes was determined to be of the order of 105 mol L−1. The effects of chain length on the morphology and wettability of the polymers on silicon substrates were studied using atomic force microscopy. Three distinct dewetting patterns, i.e. spherical domains, fractal structures and ring structures, were observed with variation in the pendant chain length. This ability to control the thin‐film morphology of the polymers may have potential technological applications, which include but are not limited to sensors, fluorescent coatings and organic electronics. © 2018 Society of Chemical Industry

show abstract

Synthesis and characterization of novel triptycene dianhydrides and polyimides of intrinsic microporosity based on 3,3ʹ-dimethylnaphthidine

Cited by 50 publications

References 36 publications

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

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

Microporous Organic Materials for Membrane‐Based Gas Separation

Triptycene‐based fluorescent polymers with pendant alkyl chains: interaction with fullerenes and morphology of thin films

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