Pyrene-directed growth of nanoporous benzimidazole-linked nanofibers and their application to selective CO2 capture and separation

Rabbani, Mohammad Gulam; Sekizkardes, Ali K.; El‐Kadri, Oussama M.; Kaafarani, Bilal R.; El‐Kaderi, Hani M.

doi:10.1039/c2jm34922a

Cited by 143 publications

(104 citation statements)

References 68 publications

(50 reference statements)

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“…PIN1 and PIN1_2 exhibit the same CO 2 /N 2 selectivity factor of 30. These values are comparable with other imine-based polymers PAN-1(35),80 APOPs (20-31), 39 PI-1 (27) 40 or other triazine-based polymers NOPs(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39), 82. Nevertheless, these selectivity factors are lower than those of PCN-AD (112),73 …”

supporting

confidence: 67%

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

et al. 2015

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Porous imine-linked networks (PINs) have been prepared by catalyst-free Schiff base condensation of 2,4,6-(4-aminophenyl)1,3,5-triazine with 9,10-anthracene-dicarboxaldehyde (PIN1 and PIN1_2) and with 4,4 0 ,4 00 ,4 000 -methanetetrakis-benzaldehyde (PIN2). Even after synthesis optimisation, only with DMSO (PIN1 and PIN2) microporous frameworks were obtained, whereas DMF (PIN1_2) and other solvents led to nonporous systems, estimated by argon measurements. Furthermore, 15 N solid state NMR and IR spectroscopy reveal the influence of the decomposition products of DMSO leading to protonation of the imine linkage and resulting in an ionic structure with an incorporated sulfonic counterion. Until now, protonation of an imine function due to the usage of DMSO as solvent has not been discussed in the literature. In contrast, for PIN1_2 the imine linkage remains neutral. Argon sorption isotherms for PIN1 and PIN2 exhibit surface areas of 458 m 2 g À1 and 325 m 2 g À1 and the pore structure displays micro-and small mesopores with pore diameters from 0.6 to 5 nm. Additionally, CO 2 isotherms at 273 K demonstrate ultramicropores for all three polymers with similar pore size distributions. Despite their different network structures, similar CO 2 uptakes (1.8-1.06 mmol g À1 at 273 K at 1.0 bar) and heat of adsorption Q st values of 30 kJ mol À1 were obtained. In line with the polyionic character of PIN1 and PIN2, both compounds adsorb three times more water than the more hydrophobic, neutral PIN1_2 at room temperature indicating two different adsorption mechanisms. IAST selectivity calculations show good CO 2 /N 2 (30-31) and CO 2 /CH 4 (8-12) selectivity factors. Despite their moderate BET-surface areas, the PINs show good CO 2 uptakes and selectivity factors.

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confidence: 67%

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

et al. 2015

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“…Pristine AB-COF shows a CO 2 uptake of 3.38 mmol g -1 at 273 K. The metal-doped forms of AB-COF exhibit enhanced carbon dioxide uptake of 4.68 mmol g -1 (Zn@AB-COF) and 4.33 mmol g -1 (Li@AB-COF), which is an increase by 38% and 28%, respectively, compared to the undoped AB-COF. The doped COF thus outperforms most porous polymers such as BILP-10 (4.02 mmol g -1 ), 50 PPN-6-SO 3 Li (4.26 mmol g -1 ) 51 and CTF-6PM (4.20 mmol g -1 ) 52 , PCTF-1 (3.24 mmol g -1 ) 6 , PCTF-5 (2.58 mmol g ¬-1 ) 7 and, to the best of our knowledge, surpasses all 2D and 3D COFs reported to date, such as TpPa-1 (3.57 mmol g -1 ), 20 COF-6 (3.84 mmol g -1 ) 5 or 3D COF-103 (1.73 mmol g -1 ). 5 With increasing temperature (298 K and 313 K, ESI, Figure 4b and d) the advantage of doping becomes gradually less apparent.…”

Section: Resultsmentioning

confidence: 99%

Tunable Water and CO₂ Sorption Properties in Isostructural Azine-Based Covalent Organic Frameworks through Polarity Engineering

et al. 2015

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The use of covalent organic frameworks (COFs) in environmental settings such as atmospheric water capture or CO 2 separation under realistic pre-and post-combustion conditions is largely unexplored to date. Herein, we present two isostructural azine-linked COFs based on 1,3,5-triformyl benzene (AB-COF) and 1,3,5-triformylphloroglucinol (ATFG-COF) and hydrazine building units, respectively, whose sorption characteristics are precisely tunable by the rational design of the chemical nature of the pore walls. This effect is particularly pronounced for atmospheric water harvesting, which is explored for the first time using COFs as adsorbents. We demonstrate that the less polar AB-COF acts as a reversible water capture and release reservoir, featuring among the highest water vapor uptake capacity at low pressures reported to date (28 wt% at <0.3 p p 0 -1 ). Furthermore, we show tailored CO 2 sorption characteristics of the COFs through polarity engineering, demonstrating high CO 2 uptake at low pressures ( < 1bar) under equilibrium (sorption isotherm) and kinetic conditions (flow TGA, breakthrough) for the more polar ATFG-COF, and very high CO 2 over N 2 (IAST: 88) selectivity for the apolar AB-COF. In addition, the pore walls of both COFs were modified by doping with metal salts (lithium and zinc acetate), revealing an extremely high CO 2 uptake of 4.68 mmol g -1 at 273 K for the zinc-doped AB-COF.

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“…Recently, POPs which can be constructed from light-weight elements linked by strong covalent bonds have attracted increasing attention for gas adsorption, storages and separation owing to their high stability against moisture, chemical stability with long lifetimes and easy handling [15]. These are known by their different product designations, such as Schiff base networks (SNWs) [16], benzimidazole-linked polymers (BILPs) [17], covalent triazine frameworks (CTFs) [18], polymers with intrinsic microporosity (PIMs) [19], porous aromatic frameworks (PAFs) [20], porous polymer frameworks (PPFs) [21], porous polymer networks (PPNs) [22], covalent organic frameworks (COFs) [23], element-organic frameworks (EOFs) [24], covalent organic polymers (COPs) [25], hypercrosslinked and conjugated microporous polymers (HCPs and CMPs) [26,27], covalent imine polymers (CIP) [28], and nitrogen-doped porous carbon materials (NPCs) [29]. The relatively low cost synthesis of this class of nitrogen chloride-catalyzed Friedel-Crafts reaction [33].…”

Section: Introductionmentioning

confidence: 99%

Covalent triazine polymers using a cyanuric chloride precursor via Friedel–Crafts reaction for CO2 adsorption/separation

Puthiaraj

Kim

Ahn

2016

Chemical Engineering Journal

103

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Pyrene-directed growth of nanoporous benzimidazole-linked nanofibers and their application to selective CO2 capture and separation

Cited by 143 publications

References 68 publications

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

Tunable Water and CO₂ Sorption Properties in Isostructural Azine-Based Covalent Organic Frameworks through Polarity Engineering

Covalent triazine polymers using a cyanuric chloride precursor via Friedel–Crafts reaction for CO2 adsorption/separation

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Pyrene-directed growth of nanoporous benzimidazole-linked nanofibers and their application to selective CO2 capture and separation

Cited by 143 publications

References 68 publications

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

Tunable Water and CO2 Sorption Properties in Isostructural Azine-Based Covalent Organic Frameworks through Polarity Engineering

Covalent triazine polymers using a cyanuric chloride precursor via Friedel–Crafts reaction for CO2 adsorption/separation

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Tunable Water and CO₂ Sorption Properties in Isostructural Azine-Based Covalent Organic Frameworks through Polarity Engineering