244272-22-8

Upstream product

• 1271-48-3 1,1'-ferrocenyldicarboxaldehyde 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

Syntheses, structures of N-(substituted)-2-aza-[3]-ferrocenophanes and their application as redox sensor for Cu2+ ion

Rigid N-(substituted)-2-aza-[3]-ferrocenophanes L1 and L2 were easily synthesized from 1,1 -dicarboxyaldehydeferrocene and the corresponding amines. Ligands L1 and L2 were characterized by 1H NMR, 13C NMR and single-crystal X-ray crystallography. The coordination abilities of L1 and L2 with metal ions such as Cu2+, Mg2+, Ni2+, Zn2+, Pb2+ and Cd2+ were evaluated by cyclic voltammetry. The electrochemical shift (ΔE1/2) of 125 mV was observed in the presence of Cu2+ ion, while no significant shift of the Fc/Fc + couple was observed when Mg2+, Ni2+, Zn 2+, Pb2+, Cd2+ metal ions were added to the solution of L1 in the mixture of MeOH and H2O. Moreover, the extent of the anodic shift of redox potentials was approximately equal to that induced by Cu2+ alone when a mixture of Cu2+, Mg2+, Ni2+, Zn2+, Pb2+ and Cd2+ was added to a solution of L1. Ligand L1 was proved to selectively sense Cu2+ in the presence of large, excessive first-row transition and late-transition metal cations. The coordination model was proposed from the results of controlled experiments and quantum calculations.

Aminomethyl-substituted ferrocenes and derivatives: Straightforward synthetic routes, structural characterization, and electrochemical analysis

A variety of aminomethyl-substituted ferrocenes and the parent compounds (iminomethyl)ferrocenes, azaferrocenophanes, and diferrocenylamines can be selectively synthesized from reductive amination of 1,1′-diformylferrocene or formylferrocene. The optimized one- or two-step reactions have delivered 13 new compounds, isolated in 65-97% yields, which include tertiary (ferrocenylmethyl)amines and azaferrocenophanes by using NaBH(OAc)3 as a mild reducing agent and (iminomethyl)ferrocenes and secondary (ferrocenylmethyl)amines by using LiAlH4. X-ray structures of representative members of these ferrocene derivative families have evidenced the preferred conformation adopted by ferrocene backbones, in which surprisingly the steric hindrance is apparently not systematically minimized. 15N NMR measurements on aminomethyl-substituted ferrocenes and derivatives are provided for the first time, establishing benchmark values ranging from -330 to -305 ppm (nitromethane δ 0 ppm). The cyclic voltammetry of these species evidences two clearly distinct oxidation potentials related to the iron(II) center and the amino function. These aminomethyl-substituted ferrocenes are potentially valuable for further ortho-directed functionalization of ferrocene.

N-Substituted 2-aza-[3]-ferrocenophanes. New synthesis using RuCl2(PPh3)3 catalyzed condensation, structure, and electrochemical behavior

The reactions of 1,1′-ferrocenedimethanol with arylamine and with alkylamine in the presence of RuCl2(PPh3)3 catalyst led to condensation of CH2OH and NH groups to afford N-alkyl-(or N-aryl-)2-aza-[3]-ferrocenop

Preparation and characterization of various N-substituted-2-aza-[3]-ferrocenophanes and their chemical and electrochemical properties

RuCl2(PPh3)3 catalyzed condensation of 1,1′-ferrocenedimethanol with primary amines afforded N-alkyl- or N-aryl-2-aza-[3]-ferrocenophanes which were characterized by 1H and 13C NMR spectra. X-ray crystallography of N-(4-butylphenyl)-2-aza-[3]-ferrocenophane unequivocally revealed its mononuclear structure. The N-C (aryl) bond distance is shorter than the N-CH2 single bond due to extension of π-conjugation of the aromatic ring to the nitrogen atom. N-Hexyl-2-aza-[3]-ferrocenophane reacts with methyl iodide to give the N-methylated product which was characterized by NMR spectroscopy and X-ray crystallography. N-Aryl-2-aza-[3]-ferrocenophanes exhibited reversible redox between ferrocene and ferrocenium cations and an irreversible oxidation peak at a higher oxidation potential.