One-pot cascade construction of nonsubstituted quinoline-bridged covalent organic frameworks

Pang, Huaji; Huang, Dekang; Zhu, Yanqiu; Zhao, Xiaodong; Xiang, Yonggang

doi:10.1039/d2sc06044b

Cited by 23 publications

(29 citation statements)

References 47 publications

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“…In our previous study, it was reported that NQ-COFs linked by nonsubstituted quinoline exhibited a higher photogenerated efficiency of •O 2 – compared to the corresponding imine-linked COFs . In the present investigation, the ability of photogenerated •O 2 – by Am-COF D4 was evaluated using electron paramagnetic resonance (EPR) measurements (Figure f).…”

Section: Resultsmentioning

confidence: 75%

“…In the present investigation, the ability of photogenerated •O 2 – by Am-COF D4 was evaluated using electron paramagnetic resonance (EPR) measurements (Figure f). However, the weakest signals of •O 2 – adducts in the presence of 5,5-dimethyl-1-pyrroline N -oxide (DMPO) were observed, and then the inapplicability of Am-COF D4 to •O 2 – -mediated reactions was demonstrated by the photocatalytic synthesis of benzimidazoles . Subsequently, various types of photocatalytic organic transformations were evaluated, and the dehalogenation of α-bromoacetophenone derivatives, which is driven by the singlet electron transfer (SET), was selected for further investigation .…”

Section: Resultsmentioning

confidence: 99%

“…In our previous study, it was reported that NQ-COFs linked by nonsubstituted quinoline exhibited a higher photogenerated efficiency of •O 2 − compared to the corresponding iminelinked COFs. 41 In the present investigation, the ability of photogenerated •O 2 − by Am-COF D4 was evaluated using electron paramagnetic resonance (EPR) measurements (Figure 4f). However, the weakest signals of •O 2 − adducts in the presence of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) were observed, and then the inapplicability of Am-COF D4 to •O 2 −mediated reactions was demonstrated by the photocatalytic synthesis of benzimidazoles.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…40 Recently, our group developed an oxidant-free method for producing nonsubstituted quinoline-linked COFs, which demonstrated superior photocatalytic activity for superoxide anion radical (•O 2 − ) generation. 41,42 These mild reactions allow for the incorporation of more functional photocatalytic units into COFs. In addition, the oxidative conversion of imine-linked COFs to stable amidelinked COFs (Am-COFs) using NaClO 2 and oxone has been achieved.…”

Section: ■ Introductionmentioning

confidence: 99%

“…To improve the compatibility of functional groups in the oxidative reactions, photocatalytic synthesis was employed to construct benzoxazole-bridged COFs . Recently, our group developed an oxidant-free method for producing nonsubstituted quinoline-linked COFs, which demonstrated superior photocatalytic activity for superoxide anion radical (•O 2 – ) generation. , These mild reactions allow for the incorporation of more functional photocatalytic units into COFs. In addition, the oxidative conversion of imine-linked COFs to stable amide-linked COFs (Am-COFs) using NaClO 2 and oxone has been achieved. − Although Am-COFs were first obtained in 2016, their photocatalytic performance has rarely been explored.…”

Section: Introductionmentioning

confidence: 99%

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Construction of Amide-Linked Covalent Organic Frameworks by N-Heterocyclic Carbene-Mediated Selective Oxidation for Photocatalytic Dehalogenation

Wang,

Huang,

Zheng

et al. 2023

Chem. Mater.

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Linkage conversion of imine to amide can not only boost the stability of covalent organic frameworks (COFs) but also enhance their functionality. However, current methods for generating amide linkages usually involve the use of inorganic oxidants, such as NaClO 2 and oxone, which have a severe drawback of functional group incompatibility. In this study, we introduced a novel synthetic strategy to fabricate amide-linked COFs (Am-COFs) through N-heterocyclic carbene-mediated aerobic oxidation of C�N bonds in the corresponding imine-linked COFs. This protocol not only featured mild reaction conditions, high crystallinity retention, quantitative conversion efficiency, and generality but, most importantly, delivered great compatibility with functional groups due to the umpolung of imine. Accordingly, we successfully synthesized Am-COF D19 and Am-COF R3 , which contained oxidant-susceptible dibenzothiophene and vinyl groups, respectively. Am-COF D19 exhibited excellent photocatalytic dehalogenation activity of α-bromoacetophenone, while Am-COF R3 underwent intramolecular hydroamidation to yield dihydroisoquinolinone-linked 2HQ-COF R3 that has never been reported before. The discovery of this strategy is expected to expedite the application of amide-linked COFs.

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Construction of Amide-Linked Covalent Organic Frameworks by N-Heterocyclic Carbene-Mediated Selective Oxidation for Photocatalytic Dehalogenation

Wang,

Huang,

Zheng

et al. 2023

Chem. Mater.

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Embedding Hydrogen Atom Transfer Moieties in Covalent Organic Frameworks for Efficient Photocatalytic C−H Functionalization

Pang,

Liu,

Huang

et al. 2023

Angewandte Chemie

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Covalent organic frameworks (COFs) have emerged as efficient heterogeneous photocatalysts for a wide range of relatively simple organic reactions, whereas their application in complex organic transformations, like site‐selective functionalization of unactivated C−H bonds, is underexplored, which can be mainly attributed to the lack of highly active organophotocatalytic cores. Herein through bonding oxygen atoms at the N‐terminus of quinolines in nonsubstituted quinoline‐linked COFs (NQ−COFs), we successfully realized the embedding of active hydrogen atom transfer (HAT) moieties into the skeleton of COFs. This novel designed COF (NQ−COFE5−O), serving as both an excellent photosensitizer and HAT catalyst, exhibited much higher efficiency in C−H functionalization than the corresponding NQ−COFE5. Specially, we evaluated the photocatalytic performance of NQ−COFE5−O on ten different substrates, including quinolines, benzothiazole, and benzoxazole, all of which were transferred to desired products in moderate to high yields (up to 93 %). Furthermore, the as‐synthesized NQ−COFE5−O displayed excellent photostability and could be reused with negligible loss of activity for five catalytic cycles.

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Covalent Organic Frameworks: Opportunities for Rational Materials Design in Cancer Therapy

Zhou,

Guan,

Dong

2023

Angewandte Chemie

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Nanomedicines are extensively used in cancer therapy. Covalent organic frameworks (COFs) are crystalline organic porous materials with several benefits for cancer therapy, including porosity, design flexibility, functionalizability, and biocompatibility. This review examines the use of COFs in cancer therapy from the perspective of reticular chemistry and function‐oriented materials design. First, the modification sites and functionalization methods of COFs are discussed, followed by their potential as multifunctional nanoplatforms for tumor targeting, imaging, and therapy by integrating functional components. Finally, some challenges in the clinical translation of COFs are presented with the hope of promoting the development of COF‐based anticancer nanomedicines and bringing COFs closer to clinical trials.

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One-pot cascade construction of nonsubstituted quinoline-bridged covalent organic frameworks

Abstract: Irreversible locking of imine linkage into stable linkages represents a promising strategy to improve the robustness and functionality of covalent organic frameworks (COFs). We report, for the first time, a...

Cited by 23 publications

References 47 publications

Construction of Amide-Linked Covalent Organic Frameworks by N-Heterocyclic Carbene-Mediated Selective Oxidation for Photocatalytic Dehalogenation

Construction of Amide-Linked Covalent Organic Frameworks by N-Heterocyclic Carbene-Mediated Selective Oxidation for Photocatalytic Dehalogenation

Embedding Hydrogen Atom Transfer Moieties in Covalent Organic Frameworks for Efficient Photocatalytic C−H Functionalization

Covalent Organic Frameworks: Opportunities for Rational Materials Design in Cancer Therapy

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