1350906-83-0Relevant articles and documents
Aldimines generated from aza-Wittig reaction between bis(iminophosphoranes) derived from 1,1′-diazidoferrocene and aromatic or heteroaromatic aldehydes: Electrochemical and optical behaviour towards metal cations
Sola, Antonia,Oton, Francisco,Espinosa, Arturo,Tarraga, Alberto,Molina, Pedro
, p. 12548 - 12559 (2011)
Aldimine 4 bearing a 2-quinolyl group was prepared by aza-Wittig reaction between the triphenyliminophosphorane derived from the 1,1′- diazidoferrocene and 2-formylquinoline. However, aldimine 5, bearing a pyrene ring, was prepared using the most reactive tributyliminophosphorane derivative and the corresponding 1-formylpyrene. On the other hand, formation of aldimine 8 involves a tandem process, Staudinger reaction/intramolecular aza-Wittig reaction, by using directly 1,1′-diazidoferrocene and 2- (diphenylphosphonyl)benzaldehyde. Aldimine 4 behaves as chemosensor molecule for Ni2+, Zn2+, Cd2+, Hg2+ and Pb 2+ cations through two different channels: electrochemical (ΔE1/2 = 222-361 mV) and chromogenic (Δλ = 122-153 nm), which can be used for the "naked eye" detection of these metal cations. Aldimine 5 behaves as a highly selective redox (in CH3CN) and fluorescent (in CH3Cl-DMF) probe for Hg2+ metal cations even in the presence of a large excess of the other metal cations tested. Aldimine 8 displays electrochemical affinity (ΔE1/2 = 60-288 mV) to Li+, Ca2+, Mg2+, Zn2+ and Pb2+ metal cations, with the phosphorus oxide functionality as a binding site. From the 1H NMR titration data as well as DFT calculations, different tentative binding modes have been established, for these structurally related ferrocenyl derivatives. The Royal Society of Chemistry.
