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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines.
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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
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Updated: May 16, 2025

Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
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Marco orgánico covalente en 2D

José Del Refugio Monroy1,2, Tejas Deshpande3, Joël Schlecht2

  • 1Department of Chemistry & Center for the Science of Materials Berlin, Humboldt-Universität zu Berlin, Brook-Taylor-Strasse 2, Berlin 12489, Germany.

Journal of the American Chemical Society
|May 15, 2025
PubMed
Resumen

Los investigadores crearon marcos orgánicos covalentes bidimensionales quirales (HeliCOFs) utilizando bloques de construcción de heliceno. Estos nuevos marcos exhiben propiedades quirópticas y fotoluminiscentes únicas, avanzando en la ciencia de los materiales quirales.

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Área de la Ciencia:

  • Ciencias de los materiales
  • Química orgánica
  • Química supramolecular

Sus antecedentes:

  • La síntesis de marcos orgánicos covalentes homoquirales 2D (COF) es difícil debido a los problemas de apilamiento con las unidades quirales.
  • La quiralidad helicoidal ofrece una ruta prometedora para controlar el montaje y las propiedades del marco.

Objetivo del estudio:

  • Para introducir la quiralidad helicoidal en los FOC 2D utilizando [5] los enlaces de heliceno.
  • Investigar las propiedades estructurales, quirópticas y fotoluminiscentes de los heliCOF resultantes [5].

Principales métodos:

  • Utilizó helicenos enantiopuros y racémicos [5] estables en su configuración como bloques de construcción.
  • Reacciones de condensación empleadas con el 1,3,5-triformilbenceno (TFB) o el 1,3,5-triformilfloroglucinol (TFP).
  • Se han caracterizado los helicofenoles sintetizados [5] en forma de polvos y películas delgadas homogéneas.

Principales resultados:

  • Eficientemente formado homoquiral y racémica 2D [5]HeliCOFs con características estructurales distintas.
  • Propiedades quirópticas avanzadas observadas en el espectro visible rojo lejano debido a la quiralidad helicoidal propagada.
  • Propiedades fotoluminiscentes reveladas en [5]HeliCOF películas delgadas de celosías conjugadas ordenadas π.

Conclusiones:

  • Integró con éxito la quiralidad helicoidal en COFs 2D, creando [5]HeliCOFs.
  • Demostró que la quiralidad helicoidal influye en la estructura del marco y las propiedades ópticas.
  • Extendió la regla de Liebisch-Wallach a los COF 2D, proporcionando información sobre la formación del marco quiral.