Pinwheel-like Curved Aromatics from the Cyclotrimerization of Strained Alkyne Cycloparaphenylenes

13 February 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Curved aromatic hydrocarbons often display better solubility and more desirable electronic properties in comparison to their flat counterparts. Macrocyclic curved aromatics possess these traits as well as shape-persistent pores ideal for host-guest interactions. A quintessential macrocyclic curved aromatic molecule is the cycloparaphenylene, or [n]CPP. Our group has developed a new class of these carbon nanohoops, called [n+1]CPPs, that incorporate a strained alkyne (“+1”) into the carbon backbone. We have previously shown the [n+1]CPPs to be a promising new class of strain-promoted azide-alkyne cycloaddition click reagents. Herein, we show that the [n+1]CPPs can also be converted into pinwheel-like multi-pore large molecules via a straightforward and high yielding metal-mediated alkyne cyclotrimerization reaction. We provide insight into suitable metals for this transformation, the photophysics of these trimeric molecules, as well as their strain profiles and crystal packing.


curved aromatic

Supplementary materials

Supplementary information
Experimental details, NMR spectra, photophysical characterization, crystallographic information, and computational details.

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