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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Nile Red-Based Covalent Organic Framework as a Photocatalyst for C-H Bond Functionalization.

Marta Gordo-Lozano1, Diego G Matesanz2,3, Marcos Martínez-Fernández1

  • 1Macromolecular and Heterocyclic Organic Materials Group, Organic Chemistry Department, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Madrid 28040, Spain.

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|June 26, 2025
PubMed
Summary

Researchers developed a novel covalent organic framework (COF) photocatalyst, NR0.17-COF, for efficient C-H functionalization. This recyclable material enables scalable organic synthesis under mild conditions, advancing photocatalytic technology.

Keywords:
COFC−H functionalizationNile Redheterogeneous catalysisphotocatalysis

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Photocatalysis

Background:

  • Covalent organic frameworks (COFs) are of interest as photocatalysts.
  • Symmetry restrictions in linkers hinder the development of heterogeneous photocatalysts.
  • Postmodification offers a route to overcome these limitations.

Purpose of the Study:

  • To synthesize a novel imine-based 2D-COF, NR0.17-COF, via postmodification with a Nile Red (NR) unit.
  • To evaluate the photocatalytic activity of NR0.17-COF in C-H functionalization reactions.
  • To demonstrate the scalability and recyclability of the developed heterogeneous photocatalyst.

Main Methods:

  • Synthesis of an imine-based 2D-COF using a NR-alkyne scaffold for postmodification.
  • Application of NR0.17-COF in various photoredox-catalyzed C-H functionalization reactions.
  • Assessment of radical generation, functional group tolerance, scalability, and recyclability.

Main Results:

  • NR0.17-COF exhibits remarkable photocatalytic activity in C-H functionalization under mild conditions and low-energy light.
  • The framework effectively generates aryl, sulfur, and nitrogen radicals with good functional group tolerance.
  • The heterogeneous photocatalyst demonstrates a 10-fold increase in reaction scale and recyclability up to six times, outperforming homogeneous systems.

Conclusions:

  • Post-synthetic modification of COFs is a viable strategy for developing efficient heterogeneous photocatalysts.
  • NR0.17-COF offers a scalable, recyclable, and versatile solution for photoredox-catalyzed C-H functionalization.
  • This advancement holds significant potential for practical applications in organic synthesis and photocatalytic technology.