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      Reversible adsorption and storage of secondary explosives from water using a Tröger's base-functionalised polymer

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          Abstract

          A Tröger's base-derived covalent organic polymer ( TB-COP) was synthesised and used as an adsorbent for the reversible adsorption of picric acid from water.

          Abstract

          A Tröger's base-functionalised covalent organic polymer ( TB-COP) was synthesised and used as an adsorbent for the efficient removal of picric acid (PA) from water through the use of weak and reversible supramolecular interactions such as hydrogen bonding and π–π interactions. TB-COP was readily synthesised in quantitative yield using a one-pot metal-free polymerisation reaction strategy between a semi-flexible aromatic triamine [ L; benzene-1,3-5-tricarboxylic acid-tris-(4-amino-phenyl-amide)] and dimethoxymethane. The molecular structure, physicochemical and morphological characteristics of TB-COP were analysed by using various spectroscopic and imaging techniques. Thermogravimetric analysis showed TB-COP to be thermally stable up to 380 °C; while the calculated Brunauer–Emmett–Teller (BET) surface area was found to be 34 m 2 g −1 at 273 K. The picric acid adsorption study of the activated TB-COP showed an excellent adsorption capacity of ca. 90% within 60 minutes of contact time at 298 K (Langmuir isotherm model: K L = 0.0541 ± 6 L mg −1, R 2 = 0.9962); the adsorption efficiency being shown to improve with increasing temperature. The extraction of PA was also clearly visible to the naked eye, where the yellow colored PA solution became transparent upon addition of TB-COP. Other interfering phenolic organic pollutants showed poor to moderate adsorption efficiency. Importantly, TB-COP could be used to store PA over a long period of time in a safe manner, without any leakage or any significant loss in extraction efficiency. Moreover, the polymer could be reused for several adsorption cycles, as PA could be released back into the solution by simply changing the pH of the aqueous media. This makes TB-COP an extremely promising material for the selective and efficient removal of picric acid from water, and TB-COP can be considered as being a ‘fast’ and naked eye colorimetric indicator for such analytes.

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          Most cited references 88

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          Porous, crystalline, covalent organic frameworks.

          Covalent organic frameworks (COFs) have been designed and successfully synthesized by condensation reactions of phenyl diboronic acid {C6H4[B(OH)2]2} and hexahydroxytriphenylene [C18H6(OH)6]. Powder x-ray diffraction studies of the highly crystalline products (C3H2BO)6.(C9H12)1 (COF-1) and C9H4BO2 (COF-5) revealed expanded porous graphitic layers that are either staggered (COF-1, P6(3)/mmc) or eclipsed (COF-5, P6/mmm). Their crystal structures are entirely held by strong bonds between B, C, and O atoms to form rigid porous architectures with pore sizes ranging from 7 to 27 angstroms. COF-1 and COF-5 exhibit high thermal stability (to temperatures up to 500 degrees to 600 degrees C), permanent porosity, and high surface areas (711 and 1590 square meters per gram, respectively).
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            Covalent organic frameworks.

            Covalent organic frameworks (COFs) are a class of crystalline porous polymers that allow the atomically precise integration of organic units to create predesigned skeletons and nanopores. They have recently emerged as a new molecular platform for designing promising organic materials for gas storage, catalysis, and optoelectronic applications. The reversibility of dynamic covalent reactions, diversity of building blocks, and geometry retention are three key factors involved in the reticular design and synthesis of COFs. This tutorial review describes the basic design concepts, the recent synthetic advancements and structural studies, and the frontiers of functional exploration.
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              Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications.

              Dihydrogen, methane, and carbon dioxide isotherm measurements were performed at 1-85 bar and 77-298 K on the evacuated forms of seven porous covalent organic frameworks (COFs). The uptake behavior and capacity of the COFs is best described by classifying them into three groups based on their structural dimensions and corresponding pore sizes. Group 1 consists of 2D structures with 1D small pores (9 A for each of COF-1 and COF-6), group 2 includes 2D structures with large 1D pores (27, 16, and 32 A for COF-5, COF-8, and COF-10, respectively), and group 3 is comprised of 3D structures with 3D medium-sized pores (12 A for each of COF-102 and COF-103). Group 3 COFs outperform group 1 and 2 COFs, and rival the best metal-organic frameworks and other porous materials in their uptake capacities. This is exemplified by the excess gas uptake of COF-102 at 35 bar (72 mg g(-1) at 77 K for hydrogen, 187 mg g(-1) at 298 K for methane, and 1180 mg g(-1) at 298 K for carbon dioxide), which is similar to the performance of COF-103 but higher than those observed for COF-1, COF-5, COF-6, COF-8, and COF-10 (hydrogen at 77 K, 15 mg g(-1) for COF-1, 36 mg g(-1) for COF-5, 23 mg g(-1) for COF-6, 35 mg g(-1) for COF-8, and 39 mg g(-1) for COF-10; methane at 298 K, 40 mg g(-1) for COF-1, 89 mg g(-1) for COF-5, 65 mg g(-1) for COF-6, 87 mg g(-1) for COF-8, and 80 mg g(-1) for COF-10; carbon dioxide at 298 K, 210 mg g(-1) for COF-1, 779 mg g(-1) for COF-5, 298 mg g(-1) for COF-6, 598 mg g(-1) for COF-8, and 759 mg g(-1) for COF-10). These findings place COFs among the most porous and the best adsorbents for hydrogen, methane, and carbon dioxide.
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                Author and article information

                Journal
                JMCAET
                Journal of Materials Chemistry A
                J. Mater. Chem. A
                Royal Society of Chemistry (RSC)
                2050-7488
                2050-7496
                2017
                2017
                : 5
                : 47
                : 25014-25024
                Affiliations
                [1 ]School of Chemistry
                [2 ]Trinity Biomedical Sciences Institute (TBSI)
                [3 ]Trinity College Dublin
                [4 ]The University of Dublin
                [5 ]Dublin 2
                [6 ]Centre for Research on Adaptive Nanostructures and Nanodevices (CRANN)
                Article
                10.1039/C7TA07292A
                © 2017

                http://rsc.li/journals-terms-of-use

                Product
                Self URI (article page): http://xlink.rsc.org/?DOI=C7TA07292A

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