Molecular Puzzle Ring: pseudo[1]Rotaxane from a Flexible Cyclodextrin Derivative

Citations Over TimeTop 18% of 2008 papers

Abstract

A pseudo[1]rotaxane formed by a flexible cyclodextrin (CD) derivative (1-R) with a bulky end group has been investigated on kinetic quantitation. 1-Rs have the cinnamamide moiety as a guest and a bulky end group (R) as a rate-determining moiety of the threading process. The R groups play an important role for the formation of pseudo[1]rotaxane, and kinetics of the self-inclusion process was found to be controlled by the size and shapes of the R groups. 1-Ad and 1-Me derivatives, which have an adamantyl and methyl end group, respectively, formed self-inclusion complexes by threading of the arm moiety with a conformational conversion of altrose from (1)C(4) form to (4)C(1) form. Flexibility of the altro-alpha-CD cavity resulted in an induced fit (from (1)C(4) to (4)C(1)) to the arm moiety, and introducing a bulky end group allowed the stability of this pseudo[1]rotaxane to be enhanced.

Related Papers

• → Redox Behavior of Ferrocene-Containing Rotaxane: Transposition of the Rotaxane Wheel by Redox Reaction of a Ferrocene Moiety Tethered at the End of the Axle(2004)70 cited
• → Molecular Puzzle Ring: pseudo[1]Rotaxane from a Flexible Cyclodextrin Derivative(2008)49 cited
• → Rotaxane Synthesized by End-capping via Hydroruthenation of Axle Terminal Acetylene and Its Derivation to η3-Allylruthenium Complex-containing Rotaxane(2006)21 cited
• → Structure of 6-O-α-D-Glucopyranosyl α-Cyclodextrin·8H2O(1989)12 cited
• → Supramolecular assembly of dye-modified cyclodextrin formed by inclusion of its dye-part in native cyclodextrin(1996)3 cited