Chromotropic ferrocenyl chalcone with two pyrenyl groups: Solvatochromism and molecular chemosensor for Fe(III)/Fe(II) ions

A chromotropic ferrocenyl chalcone with two pyrenyl groups (Fc-dPyr) is prepared and spectroscopically characterized. The X-ray structure analysis shows that the two pyrenyl groups are almost parallel to each other with a torsion angle of 5.57° and adopt a dimeric mode with a distance of 3.776 Å between them, ready to form an excimer. The solvatochromic fluorescence spectra indicate that the emission maxima observed in hydrogen-bonding donor (HBD) solvents (CHCl₃, EtOH and MeOH) exhibit a strictly linear relationship with the normalized E_T^N value, while those in a non-HBD solvent (CH₃CN) do not. The molecular chemosensor activity of Fc-dPyr is highly selective toward Fe(III) ions over Fe(II) ions. The fluorescence emission intensity of Fc-dPyr steeply decreases in the presence of Fe(III) ions as an oxidant, but not in the presence of Fe(II) ions.