Issue 83, 2021

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
26 ago 2021
Accepted
28 set 2021
First published
04 out 2021

Chem. Commun., 2021,57, 10887-10890

Author version available

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

X. Zhou, H. Kwon, R. R. Thompson, R. J. Herman, F. R. Fronczek, C. J. Bruns and S. Lee, Chem. Commun., 2021, 57, 10887 DOI: 10.1039/D1CC04776K

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