An aromatic micelle with bent pentacene-based panels: encapsulation of perylene bisimide dyes and graphene nanosheets

Abstract

For exploitation of a new class of aromatic micelles, we synthesized a bent pentacene-based amphiphilic molecule through Diels–Alder reaction. The amphiphiles bearing two trimethylammonium tethers assemble into a spherical aromatic micelle, with an average core diameter of 1.5 nm, in water at room temperature. The new aromatic micelle efficiently encapsulates perylene bisimide (PBI) dyes and graphene nanosheets (GNS) in water. The encapsulated PBI dyes form a parallel stacked dimer, exhibiting characteristic absorption and emission bands. In addition, the encapsulated GNS are composed of few-layer graphene sheets with an average lateral size of ∼7 nm, as confirmed by Raman spectroscopy. The resultant, aqueous host–guest complexes are stable even after three weeks in water under ambient conditions.