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IR and UV–Vis Spectroscopy of Aldehydes and Ketones01:29

IR and UV–Vis Spectroscopy of Aldehydes and Ketones

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Infrared spectroscopy, also known as vibrational spectroscopy, is mainly used to determine the types of bonds and functional groups in molecules. In aldehydes and ketones, the carbonyl (C=O) bond shows an absorption around 1710 cm-1. The C=O bond vibration of an aldehyde occurs at lower frequencies than that of a ketone. In addition to the C=O absorption in an aldehyde, the aldehydic C–H bond also gives two peaks in the 2700–2800 cm-1 range. This absorption, coupled with the...
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UV–Vis Spectroscopy of Conjugated Systems01:32

UV–Vis Spectroscopy of Conjugated Systems

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Organic compounds with conjugated double bonds show strong absorption features in the UV–visible region of the electromagnetic spectrum attributed to π → π* electronic excitations. Generally, a UV–vis absorption spectrum is recorded as a plot of absorbance vs wavelength. The wavelength of maximum absorbance, which manifests as a peak in the absorption spectrum, is denoted as λmax.
One of the factors influencing λmax is the extent of conjugation in...
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IR and UV–Vis Spectroscopy of Carboxylic Acids01:28

IR and UV–Vis Spectroscopy of Carboxylic Acids

5.2K
In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency,...
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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UV–Vis Spectroscopy: Molecular Electronic Transitions01:16

UV–Vis Spectroscopy: Molecular Electronic Transitions

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In Ultraviolet–Visible (UV–Vis) spectroscopy, the absorption of electromagnetic radiation is used to probe the electronic structure of molecules. This technique provides insights into molecular electronic transitions, particularly the movement of electrons between different molecular orbitals. Radiation is absorbed if the energy of the electromagnetic radiation passing through the molecule is precisely equal to the energy difference between the excited and ground states. During this...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals
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Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals

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Utilizando la luz visible para ajustar los equilibrios ácido-ester de boro

Joseph V Accardo1, Emily R McClure1, Martín A Mosquera1

  • 1Department of Chemistry, Northwestern University, Evanston, Illinois 60208, United States.

Journal of the American Chemical Society
|November 12, 2020
PubMed
Resumen

Los ácidos borónicos de azobenzeno ofrecen una unión diol controlada por la luz. La isomerización a la forma Z mejora significativamente la unión, lo que permite aplicaciones en materiales adaptables y conmutadores moleculares.

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Área de la Ciencia:

  • Química orgánica
  • Química supramolecular
  • Ciencias de los materiales

Sus antecedentes:

  • Los derivados del azobenzeno son conocidos como fotointerruptores.
  • Los ácidos borónicos son ampliamente utilizados en la química covalente dinámica.
  • El control de las interacciones moleculares con la luz es un desafío clave.

Objetivo del estudio:

  • Desarrollar ácidos borónicos de azobenzeno para la unión de diolos con conmutación fotovoltaica.
  • Investigar la influencia de la estructura del azobenzeno en la afinidad de unión.
  • Para demostrar aplicaciones en el reconocimiento molecular y la ciencia de los materiales.

Principales métodos:

  • Síntesis de los derivados del ácido bórico del azobenzeno.
  • Estudios de isomerización fotoquímica (isómeros E/Z).
  • Mediciones de la afinidad de unión de diol (experimentos de competencia).
  • Modelado computacional (DFT por sus siglas en inglés).
  • Fabricación y caracterización de hidrogeles.

Principales resultados:

  • Los ácidos borónicos de azobenzeno exhiben una unión diol reversible controlada por la luz.
  • La isomerización de E a Z mejora drásticamente la afinidad de unión de diolos (hasta 20 veces).
  • Las modificaciones estructurales ajustan la termodinámica de unión y los estados fotostacionarios.
  • Se ha demostrado la captura/liberación con fotointercambio de un diol etiquetado con fluoróforo.
  • Se ha desarrollado un hidrogel adaptativo covalente ajustable a la luz.

Conclusiones:

  • Los ácidos borónicos de azobenzeno proporcionan una plataforma versátil para la química covalente dinámica sensible a la luz.
  • El ajuste estructural del azobenzeno permite un control preciso de la unión del diol.
  • Estos sistemas tienen potencial en materiales inteligentes, administración de medicamentos y detección.