An oxanorbornene-fused nanocage consisting of hexaazatrinaphthylene and pyrene units

Abstract

A new oxanorbornene-fused nanocage consisting of hexaazatrinaphthylene and pyrene units was synthesized by condensation of three C-shaped tetraamine building blocks and two units of cyclohexanehexone. The structure of this D_3h-symmetric nanocage was unambiguously identified by X-ray crystallography and its reduction with SnCl₂ in a solution of HBr in acetic acid followed by oxidation with o-chloranil led to the observation of the corresponding fully conjugated nanocage by high-resolution mass spectroscopy. The photoluminescence of this oxanorbornene-fused nanocage exhibits apparent positive solvatochromism as a result of its HOMO and LUMO distributed on the pyrene and hexaazatrinaphthylene units, respectively.