Bis(naphthobipyrrolyl)methene-derived hexapyrrolic BODIPY as a single-molecule helicate with near-infrared emission

Helically twisted bis(naphthobipyrrolyl)methene-derived open-chain hexapyrroles have been synthesized as HCl salts and the corresponding BODIPY. Their solid-state structures elucidated by single-crystal X-ray diffraction analysis clearly showed the presence of intramolecular hydrogen bonds, which were concluded to play a pivotal role in stabilizing the twisted conformation. Both molecules were observed to be NIR active, with the BODIPY moiety emission extending beyond 800 nm.