An efficient synthesis of the first electroactive phosphorus-containing bisferrocene macrocycles
Abstract
Condensation reactions of the phosphodihydrazide XP(Ph)(NMeNH2)2(X = O 1a, S 1b) with ferrocene-1,1′-dicarboxaldehyde 2 afford in good yield the first examples of phosphorus ferrocenyl macrocycles Fe[C5H4CHNNMeP(X)PhNMeN
CHC5H4]2Fe (X = O 3a, S 3b) and 3b can be converted to the new compounds Fe[C5H4CH2NHNMeP(S)PhNMeNHCH2C5H4]2Fe 5 and [Fe{C5H4CH
NNMeP(S)(Me)PhNMeN
CHC5H4}2Fe][CF3SO3]26 by reaction with, respectively, LAH and CF3SO3Me; 5 represents a novel prototype of an anion receptor which electrochemically recognises the H2PO4–, HSO4– and Cl– anions.