A Near‐Infrared Absorbing and Emissive Quadruple Helicene Enabled by the Scholl Reaction of Perylene

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Abstract
Herein, we report the synthesis, structural analysis, optical and chiroptical properties of a novel quadruple helicene, which has two [6] and two [7]helicene moieties fused in a contorted framework of 92 sp2carbon atoms. It was synthesized by the Scholl reaction of a perylene‐containing substrate with the formation of eight carbon‐carbon bonds on the perylene unit in a single synthetic operation. Chemical oxidation of the quadruple helicene with tris(4‐bromophenyl)ammoniumyl hexachloroantimonate resulted in an air‐stable dication, which exhibits the same helicity in its four helicene moieties as unambiguously identified by single‐crystal X‐ray crystallography. The quadruple helicene exhibits unusual near‐infrared absorption and emission with absorption and emission maxima at 848 nm and 977 nm, respectively, and its isolated enantiomers exhibit electronic circular dichroism in the near‐infrared and visible‐light regions.
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  • University Grants Committee (Research Matching Grant)

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