REDOX-RESPONSIVE SURFACTANTS - SYNTHESIS OF 1,1-DIFERROCENYL-N-ALKANES (C-1, C-5, C-7, C-19) VIA REACTION OF (DIFERROCENYL) METHYL CARBOCATION WITH CARBANIONS

Diferrocenylmethylium cation with chloride or tetraphenylborate as cou nter-ion is prepared from diferrocenylmethanol by dehydration with str ong acids. Treatment with trimethylchrorosilane removes residual water to afford anhydrous methylium salts, which are highly reactive electr ophiles for alkylation of group 14 (carbanions), group 15 (amines), gr oup 16 (alkoxides), and, remarkably, group 17 (fluoride) nucleophiles. Reaction with long-chain carbanions yields 1,1-diferrocenyl substitut ed n-alkanes, which are of potential interest as redox-responsive surf actants. Single crystal structure analyses reveal a tendency for ambip hilic behavior to increase with increasing chain length. Medium chain length 1,1-diferrocenyl-n-alkanes show the expected intermolecular sta cking, whereas for the longest n-alkane synthesized, 1,1-diferrocenyl- n-nonadecane, intermolecular complexation with n-octadecane is observe d.