Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts

Trifluoroacetylazo dye , a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid was linked to iododye via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons and , containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons and with chemosensor units at their focal point. Conversion of () to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst , and hydrolysis produced dendrimer hosts and . Host-guest studies with a small library of amines and alcohols showed and to selectively signal certain diamines but not due to template mediated imprinting.