Enhancement of Chemical Stability and Crystallinity in Porphyrin‐Containing Covalent Organic Frameworks by Intramolecular Hydrogen Bonds

Kandambeth, Sharath; Shinde, Digambar Balaji; Panda, Manas K.; Lukose, Binit; Heine, Thomas; Banerjee, Rahul

doi:10.1002/anie.201306775

Cited by 469 publications

(377 citation statements)

References 32 publications

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“…These hollow spheres are highly porous, crystalline, chemically stable and can retain their spherical morphology in water and phosphate buffer. The chemical stability and high surface area of the COF-DhaTab arises because of the strong intramolecular hydrogen bonding that locks the phenyl rings in one plane and protects the imine nitrogen from nucleophilic attack [49][50][51][52] .…”

Section: Synthesis and Characterization Synthesis Of Cof-dhatab Andmentioning

confidence: 99%

“…31). The chemical stability of COF-DhaTab was due to the presence of the intramolecular O-H Á Á Á N ¼ C hydrogen bonding, which protects the imine bond from the attack of the nucleophiles [48][49][50][51] . Treatment with NaOH will cause the removal of the phenolic ( À OH) hydrogen, which is responsible for hydrogen bonding ( Supplementary Fig.…”

Section: Synthesis and Characterization Synthesis Of Cof-dhatab Andmentioning

confidence: 99%

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Self-templated chemically stable hollow spherical covalent organic framework

et al. 2015

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Covalent organic frameworks are a family of crystalline porous materials with promising applications. Although active research on the design and synthesis of covalent organic frameworks has been ongoing for almost a decade, the mechanisms of formation of covalent organic frameworks crystallites remain poorly understood. Here we report the synthesis of a hollow spherical covalent organic framework with mesoporous walls in a single-step template-free method. A detailed time-dependent study of hollow sphere formation reveals that an inside-out Ostwald ripening process is responsible for the hollow sphere formation. The synthesized covalent organic framework hollow spheres are highly porous (surface area B1,500 m 2 g À 1 ), crystalline and chemically stable, due to the presence of strong intramolecular hydrogen bonding. These mesoporous hollow sphere covalent organic frameworks are used for a trypsin immobilization study, which shows an uptake of 15.5 mmol g À 1 of trypsin.

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Section: Synthesis and Characterization Synthesis Of Cof-dhatab Andmentioning

confidence: 99%

Section: Synthesis and Characterization Synthesis Of Cof-dhatab Andmentioning

confidence: 99%

Self-templated chemically stable hollow spherical covalent organic framework

et al. 2015

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“…[17] Introducing intramolecular hydrogen bonding was explored by Banerjee and co-workers as a method to stabilize iminebased COFs by induced planarization of the 2D COF sheets. [18] Adv. Energy Mater.…”

Section: Long-range Ordermentioning

confidence: 99%

Photoactive and Conducting Covalent Organic Frameworks

Medina

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Bein

2017

Advanced Energy Materials

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Hierarchical functional materials with properties encoded for a defined functionality such as light‐induced charge separation are highly desirable targets of numerous synthetic efforts. In the field of reticular chemistry, 2D covalent organic frameworks are an emerging class of porous and crystalline materials obtained by bottom‐up condensation of molecular building blocks assisted by non‐bonding interactions. In this research news article, an overview is provided on newly emerging photoactive and conducting 2D covalent organic frameworks, sketching the creative trajectory from subunit design strategies to framework construction and resulting functionalities.

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“…[1][2][3][4][5][6][7] The p-units in 2D COFs not only constitute pcolumns that control the electronic functions but also shape the channel walls that form the interface for the adsorption of gases. [2][3][4] Thei ntegration of stimuli-responsive p-units into COFs is likely to yield structurally dynamic frameworks in which the structure can be transformed upon external stimulation. However, a" smart" COF is unprecedented and the possibility of structural transformation is to be exemplified.…”

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A Photoresponsive Smart Covalent Organic Framework

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Ordered p-columnar structures found in covalent organic frameworks (COFs) render them attractive as smart materials.H owever,e xternal-stimuli-responsive COFs have not been explored. Here we report the design and synthesis of ap hotoresponsive COF with anthracene units as the photoresponsive p-building blocks.T he COF is switchable upon photoirradiation to yield ac oncavo-convex polygon skeleton through the interlayer [4p+ +4p]c ycloaddition of anthracene units stacked in the p-columns.T his cycloaddition reaction is thermally reversible;h eating resets the anthracene layers and regenerates the COF.These external-stimuli-induced structural transformations are accompanied by profound changes in properties,including gas adsorption, p-electronic function, and luminescence.T he results suggest that COFs are useful for designing smart porous materials with properties that are controllable by external stimuli.

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Enhancement of Chemical Stability and Crystallinity in Porphyrin‐Containing Covalent Organic Frameworks by Intramolecular Hydrogen Bonds

Cited by 469 publications

References 32 publications

Self-templated chemically stable hollow spherical covalent organic framework

Self-templated chemically stable hollow spherical covalent organic framework

Photoactive and Conducting Covalent Organic Frameworks

A Photoresponsive Smart Covalent Organic Framework

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