Photocatalytic conversion of arylboronic acids to phenols by a new 2D donor–acceptor covalent organic framework

Luo, Bingcai; Zhang, Yubao; Chen, Ying; Huo, Jianqiang

doi:10.1039/d2ma00237j

Cited by 16 publications

(13 citation statements)

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“…Through a Schiff base reaction, Huo et al connected the electron donor benzotrithiophene (BTT) and electron acceptor 4,4 0 -(2,1,3benzothiadiazole-4,7-diyl)dianiline (BTDDA) to form the D-A structure BTT-BTDDA-COF. 288 As expected, BTT-BTDDA-COF with strong light harvesting ability, suitable energy levels and fast electron migration could be employed for the photocatalytic conversion of aryl phenyl boronic acid to phenol via the SET mechanism. Overall, as a classic electron-deficient moiety, thiadiazoles were basically used for the construction of D-A structures to reduce the bandgap and facilitate the intramolecular charge transfer channels, which is highly favorable for photocatalytic organic transformations involving SET process.…”

Section: Cof Catalystsmentioning

confidence: 53%

Reticular framework materials for photocatalytic organic reactions

Huang,

Zheng,

Chen

et al. 2023

Chem. Soc. Rev.

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Section: Cof Catalystsmentioning

confidence: 53%

Reticular framework materials for photocatalytic organic reactions

Huang,

Zheng,

Chen

et al. 2023

Chem. Soc. Rev.

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“…Benzotrithiophene (BTT) and benzothiadiazole units were combined in a donor–acceptor imine‐based COF, named as BTT‐BTDDA‐COF. [ 151 ] This material was used as heterogenous photocatalyst for hydroxylation of aryl boronic acids into phenols, under blue LED irradiation and oxygen atmosphere and using triethylamine as a sacrificial electron donor ( Figure ). Five consecutive catalytic cycles were performed without any detrimental effect in its catalytic activity or crystallinity.…”

Section: Photocatalytic Organic Transformations Mediated By Cofsmentioning

confidence: 99%

Section: Photocatalytic Organic Transformations Mediated By Cofsmentioning

confidence: 99%

Section: Structural Dimensionality and Crystallinity Of Cofs On Photo...mentioning

confidence: 99%

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Recent Advances in the Use of Covalent Organic Frameworks as Heterogenous Photocatalysts in Organic Synthesis

et al. 2023

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Organic photochemistry is intensely developed in the 1980s, in which the nature of excited electronic states and the energy and electron transfer processes are thoroughly studied and finally well‐understood. This knowledge from molecular organic photochemistry can be transferred to the design of covalent organic frameworks (COFs) as active visible‐light photocatalysts. COFs constitute a new class of crystalline porous materials with substantial application potentials. Featured with outstanding structural tunability, large porosity, high surface area, excellent stability, and unique photoelectronic properties, COFs are studied as potential candidates in various research areas (e.g., photocatalysis). This review aims to provide the state‐of‐the‐art insights into the design of COF photocatalysts (pristine, functionalized, and hybrid COFs) for organic transformations. The catalytic reaction mechanism of COF‐based photocatalysts and the influence of dimensionality and crystallinity on heterogenous photocatalysis performance are also discussed, followed by perspectives and prospects on the main challenges and opportunities in future research of COFs and COF‐based photocatalysts.

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Tetrazine‐Linked Covalent Organic Frameworks With Acid Sensing and Photocatalytic Activity

Zadehnazari,

Khosropour,

Altaf

et al. 2024

Advanced Materials

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The first synthesis and comprehensive characterization of two vinyl tetrazine‐linked covalent organic frameworks (COF), TA‐COF‐1 and TA‐COF‐2, are reported. These materials exhibited high crystallinity and high specific surface areas of 1323 and 1114 m2g–1. The COFs demonstrated favorable band positions, and narrow band gaps suitable for light‐driven applications. These advantages enabled TA‐COFs to act as reusable metal‐free photocatalysts in the arylboronic acids oxidation and light‐induced coupling of benzylamines. In addition, these TA‐COFs showed acid sensing capabilities, exhibiting visible and reversible color changes upon exposure to HCl solution, HCl vapor, and NH3 vapor. Furthermore, the TA‐COFs outperformed a wide range of previously reported COF photocathodes. The tetrazine linker in the COF skeleton represents a significant advancement in the field of COF synthesis, enhancing the separation efficiency of charge carriers during the photoreaction and contributing to their photocathodic properties. TA‐COFs can also degrade 5‐nitro‐1,2,4‐triazol‐3‐one (NTO), an insensitive explosive present in industrial wastewater, in 20 minutes in a sunlight‐driven photocatalytic process. Thus, revealing the dual functionality of the protonated TA‐COFs as both photodegradation and Brønsted acid catalysts. This pioneering work opens new avenues for harnessing the potential of the tetrazine linker in COF‐based materials, facilitating advances in catalysis, sensing, and other related fields.This article is protected by copyright. All rights reserved

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Photocatalytic conversion of arylboronic acids to phenols by a new 2D donor–acceptor covalent organic framework

Abstract: Covalent organic frameworks (COFs) are kind of promising crystalline materials for photocatalytic organic conversion. The introduction of electron donor-acceptor (D-A) units into its structure can reasonably adjust the photoelectric properties...

Cited by 16 publications

References 70 publications

Reticular framework materials for photocatalytic organic reactions

Reticular framework materials for photocatalytic organic reactions

Recent Advances in the Use of Covalent Organic Frameworks as Heterogenous Photocatalysts in Organic Synthesis

Tetrazine‐Linked Covalent Organic Frameworks With Acid Sensing and Photocatalytic Activity

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