4'-Nitroflavonol
Identifiers
3D model (JSmol)
  • InChI=1S/C15H9NO5/c17-13-11-3-1-2-4-12(11)21-15(14(13)18)9-5-7-10(8-6-9)16(19)20/h1-8,18H
    Key: YECFKQSYRZNFMD-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C(=O)C(=C(O2)C3=CC=C(C=C3)[N+](=O)[O-])O
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 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 2 3 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". Journal of Photochemistry and Photobiology A: Chemistry. 406: 112978. doi:10.1016/j.jphotochem.2020.112978. ISSN 1010-6030. S2CID 225128845.
  2. ↑ Lippert, Ernst; Kelm, Jürgen (1978-01-25). "Spektroskopische Untersuchungen über die Rolle des Käfig-Effektes bei der Prädissoziation aromatischer Nitroverbindungen". Helvetica Chimica Acta. 61 (1): 279–285. doi:10.1002/hlca.19780610125.
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