Novel photoswitchable rotaxanes

Abstract

A photoresponsive rotaxane based on the photoheterolysis of an acridane unit which is at the same time a bulky end group has been developed.

Photoswitchable ionophores based on 1,3-alternate calix[4]arenes bearing acridane units at the wide rim and bridged at the narrow rim by glycol chains

“…15 The alkoxide attacks the acridinium moiety, reverting to the starting acridane compound. The rate of the back reaction depends strongly on the solvent.…”

“…The rate of the back reaction depends strongly on the solvent. 15 Complete recovery of the starting compound requires the presence of a small amount of an alcohol. The outcome of the reaction can easily be followed by UV-visspectroscopy (see Fig.…”

N‐Substituted Acridinium as a Multi‐Responsive Recognition Unit in Supramolecular Chemistry

“…The same group also reported a photoswitchable [2]rotaxane ( 63 5+ ) composed of a cyclobis(paraquat‐ p ‐phenylene) cyclophane (“bluebox”) and a dissymmetric axis end‐functionalized with both an acridinium and an adamantane stopper (Scheme 12). [55] From the preformed pseudo‐rotaxane obtained from threading the acridane‐stoppered axis through the bluebox (log K ≈2.74), an esterification reaction between the terminal alcohol of the axis with the 1‐adamanecarbonyl chloride afforded the [2]rotaxane. During the purification process, the acridinium stopper was obtained by aromatization under acidic conditions.…”

Synthesis and characterization of dinuclear late transition-metal (copper(I), silver(I), rhenium(I)) complexes with a bis-pyridylimine ligand linked by S–S bonding

“…Current topics in the fascinating subfield of supramolecular chemistry include the supramolecular hosts for catalytic reactions [4,5], interlocked supramolecular structures with some cyclodextrins and cucurbits [6,7] and the rotary movement of catenanes [8,9]. Recent studies of copper(I) complexes containing some kinds of 2-pyridylimine ligands by Nitschke et al are particularly intriguing not only because of the stability of these complexes but also because of their unique rearrangement in solution [10][11][12].…”