Chiroptically Active Host-Guest Composites Using a Terpene-Based Micellar Capsule.

Abstract

For the design of a new chiroptically active host-guest system, a bent amphiphilic compound was synthesized using cyclic monoterpenes as key biorelated chiral frameworks. In water, the bent amphiphiles form a terpene-based micellar capsule with a core diameter of ∼2 nm in a spontaneous and quantitative fashion. The resultant chiral capsule shows wide-ranging uptake abilities toward achiral fluorescent dyes in water. Notably, relatively strong CD bands are generated from the resultant host-guest composites, e.g., possessing AIE-active tetraphenylethene and sterically demanding BODIPY dyes, through efficient host-to-guest chirality transfer. The composites also display CPL, with moderate to high emission asymmetry factors (|glum| = up to 3.3 × 10-3).