Chemistry:4'-Nitroflavonol

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4'-Nitroflavonol
4'-Nitroflavonol.png
Identifiers
3D model (JSmol)
Properties
C15H9NO5
Molar mass 283.239 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4'-Nitroflavonol is a pale yellow solid. This substance belongs to the subclass of flavonols of the class of flavonoids.

Synthesis

4'-Nitroflavonol can be synthesized by the Algar–Flynn–Oyamada reaction of the chalcone formed from 4-nitrobenzaldehyde and 2-hydroxyacetophenone.[1]

Properties

Fluorescence is reported[1] despite the presence of a nitro group at the 4' position of the molecule, which[clarification needed] is known as a fluorescence quencher.[2] An excited state intramolecular proton transfer reaction for 4'-nitroflavonol has also been observed.[1]

References

  1. 1.0 1.1 1.2 Chumak, Andrii Yu.; Mudrak, Vladyslav O.; Kotlyar, Volodymyr M.; Doroshenko, Andrey O. (2021-02-01). "4'-Nitroflavonol fluorescence: Excited state intramolecular proton transfer reaction from the non-emissive excited state" (in en). Journal of Photochemistry and Photobiology A: Chemistry 406: 112978. doi:10.1016/j.jphotochem.2020.112978. ISSN 1010-6030. 
  2. Lippert, Ernst; Kelm, Jürgen (1978-01-25). "Spektroskopische Untersuchungen über die Rolle des Käfig-Effektes bei der Prädissoziation aromatischer Nitroverbindungen" (in en). Helvetica Chimica Acta 61 (1): 279–285. doi:10.1002/hlca.19780610125.