Scalable synthesis of [8]cycloparaphenyleneacetylene carbon nanohoop using alkyne metathesis

Large scale synthesis of cycloparaphenyleneacetylenes has been challenging due to low macrocyclization yields and harsh aromatization methods that often decompose strained alkynes. Herein, a cis -stilbene-based building block is subjected to alkyne metathesis macrocylization. The following sequence of alkene-selective bromination and dehydrobromination afforded a [8]cycloparaphenyleneacetylene derivative in high yield with good scalability. X-Ray crystal structure and computational analysis revealed a unique same-rim conformation for the eight methyl groups on the nanohoop. Cycloparaphenyleneacetylene carbon nanohoops can now be prepared in a scalable manner using alkyne metathesis followed by alkene-selective bromination and dehydrobromination.