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

Abstract

Trifluoroacetylazo dye 1 , a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid 16 was linked to iododye 9 via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons 3 and 4 , containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons 18 and 19 with chemosensor units at their focal point. Conversion of 18 ( 19 ) to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst 25 , and hydrolysis produced dendrimer hosts 28 and 29 . Host-guest studies with a small library of amines and alcohols showed 28 and 29 to selectively signal certain diamines but not due to template mediated imprinting.