Redox-site accessibility of composites containing a 2D redox-active covalent organic framework: from optimization to application

Günther, Tyran; Oka, Kouki; Olsson, Sandra K.; Åhlén, Michelle; Tonai, Norimitsu; Emanuelsson, Rikard

doi:10.1039/d3ta00422h

Cited by 4 publications

(3 citation statements)

References 38 publications

(73 reference statements)

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“…To demonstrate the construction of bottlenecks, as shown in Figures 4a and 4b, the oxygen (O 2 ) and nitrogen (N 2 ) gas adsorption/desorption properties of TPDS/TPMA-Me (2) and BTDBS/TPMA-Me (3) were evaluated at 77 K. As shown in Figures S2 and S3, gas adsorption/desorption measurements were performed using TPDS/TPMA-Me (2) and BTDBS/TPMA-Me (3) after the evacuation of the template molecules. Both O 2 and N 2 did not have a dipole moment in their bonds, [14] and, as shown in Figures 2e, 2 f, and 3c, the kinetic diameter of O 2 (3.46 Å) [14] was smaller than the bottleneck (3.5 Å) of BTDBS/ TPMA-Me (3), whereas the kinetic diameter of N 2 (3.80 Å) [14] was larger than the bottlenecks (3.5 Å) of BTDBS/TPMA-Me (3). As shown in Figures 4a and 4 b, TPDS/TPMA-Me (2) adsorbed 43 mL(STP)g À 1 of O 2 at P e /P 0 = 1.02 and 2 mL(STP)g À 1 of N 2 at P e / P 0 = 1.01, respectively, while N 2 was hardly adsorbed.…”

Section: Gas Adsorption Properties Of Pos With Bottleneckmentioning

confidence: 86%

“…Porous organic materials have been expected for a wide range of applications, such as the purification, separation, and storage of gas molecules, [1] sensing of specific molecules, [1b,c,2] electrode active materials, [1b,c,3] catalysts, [1b] and reaction sites, [4] because the porous design of their components enables the modulation of the pore shape and functionalization. Metal‐organic frameworks (MOFs), [5] where organic linkers and metal‐containing nodes are connected via coordination bonds, and covalent organic frameworks (COFs), [6] where organic molecules are connected via covalent bonds, are representative examples of organic‐based porous materials.…”

Section: Introductionmentioning

confidence: 99%

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Porous Organic Salts Composed of Terphenyl Sulfonic Acid and Their Bottleneck Designability

et al. 2023

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Porous organic salts (POSs) are constructed through a strong charge‐assisted hydrogen bond between sulfonic and amino groups. The molecular design of sulfonic acid, the linker part, enables various porous structures. In the current work, we synthesized p‐terphenyl‐4,4’’‐disulfonic acid (TPDS), whose molecular structure can be easily modified by organic synthesis. Combining of TPDS and bulky tri‐p‐tolylmethanamine (TPMA‐Me), which has three methyl groups at each para‐position of the phenyl groups of triphenylmethylamine (TPMA), gave POS with one‐dimensional pore channels having two different types of bottlenecks. The central benzene ring of TPDS is exposed on the surface of the pore. Therefore, we combined 4,4′‐(benzo[c][1,2,5]thiadiazole‐4,7‐diyl)dibenzenesulfonic acid (BTDBS) containing 2,1,3‐benzothiadiazole (BT) with TPMA‐Me, and successfully constructed a one‐dimensional pore channel with a bottleneck of 3.5 Å, by exposing BT to the surface of the pore. BTDBS/TPMA‐Me exhibited a large adsorption/desorption hysteresis of nitrogen because of the bottleneck, electronic state of BT, and larger oxygen adsorption than the isostructural TPDS/TPMA‐Me. Systematic and intended modulation of the pore structure of POS based on the modification of sulfonic acid was demonstrated, and for the first time, we established a precise design methodology for a one‐dimensional pore channel with a bottleneck and high crystallinity in metal‐free porous organic materials.

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Section: Gas Adsorption Properties Of Pos With Bottleneckmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Porous Organic Salts Composed of Terphenyl Sulfonic Acid and Their Bottleneck Designability

et al. 2023

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“…In addition, a commonly used strategy to increase the electronic conductivity is the hybridisation of COFs with carbon nanotubes (CNTs), 35,50,61,65,87 reduced graphene oxide, 62,88 or conductive polymers. 63,89 The COF/CNT composites are usually synthesised by in situ polymerisation, where COF layers are grown on the CNT surface (Fig. 9).…”

Section: Hybridisation With Conductive Additivesmentioning

confidence: 99%

Organic electrodes based on redox-active covalent organic frameworks for lithium batteries

Dantas,

Ribeiro,

Souto

2024

Chem. Commun.

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Unlocking the Charge‐Storage Potential of a Phenanthraquinone‐based Two‐Dimensional Covalent Organic Framework (2D COF)

Günther,

Hedbom,

Åhlén

et al. 2024

ChemPlusChem

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The high surface area, open pore‐structure and atomic‐level organization inherent in many covalent organic frameworks (COFs) make them an attractive polymer platform for developing functional materials. Herein, a chemically robust 2D COF (TpOMe‐DAPQ COF) containing phenanthraquinone moieties was prepared by condensing 2,4,6‐trimethoxy‐1,3,5‐benzenetricarbaldehyde (TpOMe) and 2,7‐diamino‐9,10‐phenanthraquinone (DAPQ) using the convenient mechanochemical method. The poor charge‐storage capacity of the pristine TpOMe‐DAPQ COF was substantially improved by first investigating its redox‐site accessibility (RSA) using different conductivity‐enhancement methods, and then optimizing the amount of EDOT needed to perform an in‐situ polymerization. The resulting composite (0.4EDOT@TpOMe‐DAPQ) was characterized and its enhanced charge‐storage capabilities enabled it to be used as an anode material in an aqueous Mn beaker‐cell battery capable of delivering 0.76 V. This work outlines the rational design approach used to develop a functional charge‐storage material utilizing a COF‐based polymerization platform.

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Redox-site accessibility of composites containing a 2D redox-active covalent organic framework: from optimization to application

Abstract: Redox-active covalent organic frameworks (RACOFs) can be employed in various functional energy materials and applications. A crucial performance or efficiency indicator is the percentage of redox centres that can be...

Cited by 4 publications

References 38 publications

Porous Organic Salts Composed of Terphenyl Sulfonic Acid and Their Bottleneck Designability

Porous Organic Salts Composed of Terphenyl Sulfonic Acid and Their Bottleneck Designability

Organic electrodes based on redox-active covalent organic frameworks for lithium batteries

Unlocking the Charge‐Storage Potential of a Phenanthraquinone‐based Two‐Dimensional Covalent Organic Framework (2D COF)

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