Abstract
In the title compound, C19H13IO2, the dihedral angle between the naphthyl ring system and the pendant iodo-phenyl ring is 72.48 (11)°. In the crystal, C-H⋯π inter-actions and I⋯O [3.293 (2) Å] halogen bonds are observed, which combine to generate a herringbone packing motif.
Highlights
In the title compound, C19H13IO2, the dihedral angle between the naphthyl ring system and the pendant iodophenyl ring is 72.48 (11)
Our group is interested in the extended flavonol motif as it has been shown to release CO quantitatively with visible light (Popova et al, 2017). We synthesize these flavonols in two steps from an acetyl naphthol and an aromatic aldehyde
If no oxidant is added, the 20–hydroxychalcone intermediate can cyclize to a flavanone under basic conditions (Furlong et al, 1985)
Summary
Traditional CORMS (carbon monoxide-releasing molecules) contain metal carbonyls whereas photoCORMS have recently become of interest because of their ability to release CO in biological systems. Our group is interested in the extended flavonol motif as it has been shown to release CO quantitatively with visible light (Popova et al, 2017). We synthesize these flavonols in two steps from an acetyl naphthol and an aromatic aldehyde. In the title molecule (Fig. 1), the iodophenyl ring is tilted by 72.48 (11) with respect to the naphthyl ring system. (Rissanen, 2008) The crystal structure exhibits a herringbone pattern (Fig. 2) with molecules linked into [010] chains by the halogen bonding; neighboring layers are held together with van der Waals interactions along with T-shaped -stacking
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