Facile synthesis of covalent organic frameworks COF-1 and COF-5 by sonochemical method

Yang, Seung-Tae; Kim, Jun; Cho, Hye-Young; Kim, Sangho; Ahn, Wha‐Seung

doi:10.1039/c2ra21531d

Cited by 199 publications

(109 citation statements)

References 23 publications

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“…[198] Such tandem approaches could enhance the scope of COF precursors with otherwise limited solubilities and stabilities.A cid-free procedures have been developed for precursors containing labile functional groups such as metalloporphyrins. [199] Microwave-assisted [200][201][202] and sonochemical [203] syntheses as well as organic terracotta processes [204] resulted in significantly faster reactions at lower temperatures.M echanochemical approaches allowed the room-temperature and solvent-free synthesis of iminebased COFs by either manual grinding or ball milling, [205] and COF synthesis in continuous flow devices [206,207] was also reported.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

2018

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Porous organic materials are an emerging class of functional nanostructures with unprecedented properties. Dynamic covalent assembly of small organic building blocks under thermodynamic control is utilized for the intriguingly simple formation of complex molecular architectures in one-pot procedures. In this Review, we aim to analyze the basic design principles that govern the formation of either covalent organic frameworks as crystalline porous polymers or covalent organic cage compounds as shape-persistent molecular objects. Common synthetic procedures and characterization techniques will be discussed as well as more advanced strategies such as postsynthetic modification or self-sorting. When appropriate, comparisons are drawn between polymeric frameworks and discrete organic cages in terms of their underlying properties. Furthermore, we highlight the potential of these materials for applications ranging from gas storage to catalysis and organic electronics.

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

2018

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“…[198] Derartige Tandemansätze kçnnten in Zukunft die Bandbreite an zugänglichen COF-Vorstufen mit limitierten Lçslichkeiten und Stabilitäten erweitern. [199] Deutlich kürzere Reaktionszeiten bei tieferen Te mperaturen wurden in mikrowellenunterstützten [200][201][202] oder sonochemischen [203] Synthesen sowie organischen Te rracotta-Prozessen [204] erreicht. [199] Deutlich kürzere Reaktionszeiten bei tieferen Te mperaturen wurden in mikrowellenunterstützten [200][201][202] oder sonochemischen [203] Synthesen sowie organischen Te rracotta-Prozessen [204] erreicht.…”

Section: Synthese Und Charakterisierungunclassified

“…FürB austeine mit labilen funktionellen Gruppen wie Metalloporphyrine sind säurefreie Vorschriften entwickelt worden. [199] Deutlich kürzere Reaktionszeiten bei tieferen Te mperaturen wurden in mikrowellenunterstützten [200][201][202] oder sonochemischen [203] Synthesen sowie organischen Te rracotta-Prozessen [204] erreicht. Mechanochemische Verfahren ermçglichen eine lçsungsmittelfreie Synthese von Imin-COFs bei Raumtemperatur durch manuelles Verreiben oder in einer Kugelmühle, [205] und auch über COF-Synthesen in Durchflussapparaturen [206,207] wurde bereits berichtet.…”

Section: Synthese Und Prozessierungunclassified

Kovalente organische Netzwerke und Käfigverbindungen: Design und Anwendungen von polymeren und diskreten organischen Gerüsten

Beuerle

Gole

2018

Angewandte Chemie

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Poröse organische Materialien sind eine aufstrebende Klasse funktionaler Nanostrukturen mit beispiellosen Eigenschaften. Die dynamisch‐kovalente Organisation kleiner organischer Bausteine unter thermodynamischer Kontrolle wird dabei für die verblüffend einfache Bildung komplexer Architekturen in Eintopfreaktionen genutzt. In diesem Aufsatz werden die grundlegenden Designprinzipien analysiert, die zur Bildung von entweder kovalenten organischen Netzwerken als kristalline poröse Polymere oder kovalenten organischen Käfigverbindungen als formgetreue molekulare Objekte führen. Konventionelle Synthesevorschriften und Analysemethoden werden neben ausgefeilteren Strategien, wie postsynthetische Modifizierungen oder Selbstsortierung, diskutiert. Gegebenenfalls werden die entsprechenden Eigenschaften und Besonderheiten von polymeren Netzwerken und diskreten organischen Käfigen verglichen. Darüber hinaus wird das Potenzial dieser Materialien für Anwendungen, von der Gasspeicherung über die Katalyse bis hin zur organischen Elektronik, erörtert.

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“…The covered COF-5 materials were found to exhibit morphologies similar to the COF-5 material synthesized without CNTs or graphenes ( Figure S2, SI). 26,28 The FT-IR spectra also indicated the formation of COF-5; the newly appeared peaks at 1322 and 1236 cm ¹1 are attributed to the BO and CO vibrations, 26 respectively, produced by covalent bonds between boronic acids of benzene-1,4-diboronic acid (BDBA) and hydroxy groups of 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP) as shown in Figure 3 left. Furthermore, the X-ray diffraction (XRD) patterns of the hybrids showed patterns similar to the corresponding COF-5 (Figure 3 right), which agreed to previous reports, 26,28 indicating the formation of the COF-5 crystal.…”

mentioning

confidence: 94%

In Situ Synthesis of Covalent Organic Frameworks (COFs) on Carbon Nanotubes and Graphenes by Sonochemical Reaction for CO2 Adsorbents

et al. 2015

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We describe the in situ synthesis of the covalent organic framework-5 (COF-5) on the surfaces of carbon nanotubes (CNTs) and graphenes having homogeneous CNT@COF-5 coreshell structures using a sonochemical reaction in one pot. CNT@COF-5 was found to show better CO 2 adsorption than the pristine COF-5.Porous materials, especially novel porous materials having high surface areas and easily controllable chemical affinities, have been used in many applications, including gas storage and separation, 13 sensors/sensing, 4 catalysis, etc. 3,5 Metalorganic frameworks (MOFs), referred to as "molecular architectures," are built by the self-assembly of metal ions and organic linkers that form three-dimensional porous structures, and have emerged as one of the more promising materials for gas adsorbents because their pore sizes and chemical affinities are easily controllable by modifying the metals and linkers. 6,7 Covalent organic frameworks (COFs) made by covalent bonding between polyboronic acids and polydiol compounds show properties similar to the MOFs; 8,9 thus, considerable attention has currently been focused on the studies of COFs that have high potential for gas uptake.Carbon nanotubes (CNTs) and graphenes with high surface areas 10,11 have been widely used as nanomaterials in the fields of polymer reinforcements, 12 biological, 13 and electronic applications, 14 due to their remarkable electrical, thermal, optical, and mechanical properties. 1519 However, the low dispersity of the CNTs and graphenes due to the strong van der Waals interactions is a drawback of these materials for use in many areas.Aromatic molecules, such as pyrene, anthracene, triphenylene, and porphyrin derivatives, have been used as building blocks for the COFs. 9 Such molecules have a strong affinity for CNTs and graphenes due to strong ππ interactions; 2022 thus, compounds carrying such a moiety have been used as CNT-and graphene-solubilizers. 23 Based on such events, we considered that complexes of the COFs and the CNTs (or graphene) could be a candidate to improve their dispersity and gas uptake. Although there have been several reports on the synthesis of COFs on graphene-deposited substrates using a solvothermal method, 24 to the best of our knowledge, the fabrication of COF composites with bare graphene or CNTs using a facile sonochemical reaction has not yet been reported.Here we describe the preparation of COF-5 materials hybridized with CNTs (denoted as CNT@COF-5) and graphenes (graphene@COF-5) by in situ sonochemical reactions. COF-5, one of the typical COF materials, was chosen, since a sonochemical method 23 is applicable for the synthesis of this COF material in addition to a solvothermal reaction 25,26 and microwave irradiation. 27 Figure 1 shows a schematic drawing for the synthesis of a COF-5-coated CNT (see also Supporting Information (SI)). We also describe the CO 2 uptake experiment results using the prepared hybrid materials.As shown in Figure 2, the synthesized CNT@COF-5 clearly shows a thicker diameter than those of the c...

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Facile synthesis of covalent organic frameworks COF-1 and COF-5 by sonochemical method

Cited by 199 publications

References 23 publications

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

Kovalente organische Netzwerke und Käfigverbindungen: Design und Anwendungen von polymeren und diskreten organischen Gerüsten

In Situ Synthesis of Covalent Organic Frameworks (COFs) on Carbon Nanotubes and Graphenes by Sonochemical Reaction for CO2 Adsorbents

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