jo000573u_si_001.pdf (233.11 kB)
Novel Ferrocenyl Polyene Derivatives and Their Binding to Unmodified Cyclodextrins
journal contribution
posted on 2000-09-14, 00:00 authored by Jian Liu, René Castro, Khalil A. Abboud, Angel E. KaiferTwo new ferrocene derivatives, 7-ferrocenyl-2,4,6-heptatrienal (1) and 7-ferrocenyl-2,4,6-heptatrienol
(2), were synthesized and characterized. These two compounds possess a rigid triene chain
conjugated to one of the cyclopentadienyl rings of the ferrocene residue, and as a result, they exhibit
very stiff structures. The electronic absorption and electrochemical properties of these compounds
were utilized to investigate their host−guest binding interactions with the receptors α-cyclodextrin
(α-CD) and β-cyclodextrin (β-CD) in aqueous solution. From electronic absorption measurements
binding constants in the range 790−12900 M-1 were obtained; β-CD formed more stable complexes
than α-CD with both guests. Electrochemical measurements suggest some degree of site selectivity
in the complexation processes, with β-CD binding preferentially to the ferrocene moiety while α-CD
interacts with the unsaturated chain.