Novel ferrocenyl polyene derivatives and their binding to unmodified cyclodextrins

J. Liu, R. Castro, K. A. Abboud, A. E. Kaifer

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Two 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.

Original languageEnglish (US)
Pages (from-to)6973-6977
Number of pages5
JournalJournal of Organic Chemistry
Volume65
Issue number21
DOIs
StatePublished - Oct 20 2000

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Novel ferrocenyl polyene derivatives and their binding to unmodified cyclodextrins'. Together they form a unique fingerprint.

Cite this