We report the first axially chiral quateropyrene synthesized via a modular π-extension strategy combining Ir-catalyzed C-H activation, Suzuki-Miyaura cross-coupling, and Au-catalyzed alkyne benzannulation. Optimized conditions afforded the highly twisted quateropyrene backbone whose enantiomers could be separated by chiral HPLC. The extended π-system exhibits intense absorption approaching the NIR with chiroptical response. These results establish a bottom-up route to extended chiral pyrenacenes and provide insight into the optoelectronic consequences of screw-type π-extended chiral nanographenes.
Malone et al. (Wed,) studied this question.
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