Further solvent-free reactions of ferrocenylaldehydes: Synthesis of 1,1′-ferrocenyldiimines and ferrocenylacrylonitriles

Synthesis, physical and antimicrobial studies of ferrocenyl-N-(pyridinylmethylene)anilines and ferrocenyl-N-(pyridinylmethyl)anilines

“…Weaker bands appearing at longer wavelengths can be attributed to the d-d transitions. On changing solvent from nonpolar to polar, all the imines showed a bathochromic shift of p-p* transitions 75 an indication of their non-linear optics character, a behaviour that has also been observed in other ferrocenyl imine derivatives. 52,75, These spectral characteristics of the ferrocenyl-N -(pyridinylmethyl)anilines are attributed to the mixing of appreciable metal-to-ligand charge transfer (MLCT) character into their low-energy electronic excited states.…”

“…As anticipated, in all solvents, all the compounds showed a bathochromic (red) shift in comparison to pristine ferrocene. The imines and amines displayed both n-p* and p-p* transitions 60,75 in methanol. The stronger and higher energy peak were attributed to the p-p* transition of the Schiff base chromophores and the benzene ring while the weaker and less energetic peaks were assigned to the n-p* 60 transition involving the promotion of the lone pair electron of imine nitrogen atom to the antibonding p orbital associated with the Schiff base group.…”

3-Ferrocenyl-2-(4-nitrophenyl)acrylonitrile

“…The single C-C bonds around the ethylene group have a bond distance of 1.427 (7) Å for the C10-C11, which is shorter than C12-C14, 1.475 (7) Å. This difference in bond lengths has also been observed by Cao et al (2008) and Imrie et al (2007).…”

“…The nitro group of the nitrophenyl moiety is slightly twisted from the plane of the phenyl ring, with the torsion angles of C17-C16-N2-O1 and C15-C16-N2-O2 being 6.9 (7) and 6.5 (7) respectively. The ferrocenyl rings have an eclipsed conformation with a staggering angle of 15.9° which is quite large compared to a similar compound such as 3-ferrocenyl-2-(4-cyanophenyl)acrylonitrile (Imrie et al, 2007) with an angle of 1.9°. The single C-C bonds around the ethylene group have a bond distance of 1.427 (7) Å for the C10-C11, which is shorter than C12-C14, 1.475 (7) Å.…”

“…For related ferrocenylacrylonitrile structures, see : Cao & Ye (2008); Imrie et al (2007). For the synthesis of acrylonitriles, see: Liu et al (2001); Jeffery (1999); El-Tammany et al (1983); Imrie et al (2007).…”