Rotaxane dendrimers are a class of highly branched molecules containing large macrocycle rings threaded onto linear axle molecules. Type IIIB rotaxane dendrimers have branch points that connect a rod to a macrocycle and can be stimuli-responsive. The resulting dendrimers are highly complex and are relatively understudied. Synthesis of a β-cyclodextrin/azobenzene type IIIB rotaxane dendrimer was attempted. The primary synthetic target was a modified β- cyclodextrin with a maleimide functionalized handle and was accomplished using a two-pronged synthetic approach. The first route involved tosylation of β-cyclodextrin and the second utilized synthesis of a <i>N</i>-substituted maleimide using a Diels-Alder protection. The resulting maleimide-derivatized β-cyclodextrins were characterized by NMR, IR, and MP. Host-guest complexation studies between the modified β-cyclodextrin targets and azobenzene derivatives are currently under investigation using NMR to probe chemical shift changes that occur during complexation.

Synthesis of β-cyclodextrin-azobenzene type IIIB rotaxane dendrimers

ACS Spring 2022

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