Selective strain-promoted reactivity of a fluorene-derived [6]cycloparaphenyleneacetylene carbon nanohoop

Robert J. Herman; Said Jalife; Abigail G. LeBlanc; Muhammad Usama Gul Khan; Marvin L. Stewart; Sheila W. Njoroge; Sajila Riman Tanha; Frank R. Fronczek; Judy Wu; Semin Lee

doi:10.1039/D5CC05493A

Selective strain-promoted reactivity of a fluorene-derived [6]cycloparaphenyleneacetylene carbon nanohoop

Robert J. Herman,

^a Said Jalife,

^b Abigail G. LeBlanc,^a Muhammad Usama Gul Khan,

^b Marvin L. Stewart,^a Sheila W. Njoroge,

^a Sajila Riman Tanha,

^a Frank R. Fronczek,

^a Judy Wu

^b and Semin Lee

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana, USA
E-mail: seminlee@lsu.edu

^b College of Natural Science and Mathematics, University of Houston, Houston, Texas, USA

Abstract

The modular synthesis of a fluorene-based nanohoop containing six strained alkynes is described herein. We demonstrate its scalability using alkyne metathesis as the macrocyclization method and its reactivity with azides using strain-promoted azide–alkyne cycloaddition. The nanohoop undergoes two cycloadditions selectively on two oppositely located alkynes on the macrocyclic backbone.

Chemical Communications

Selective strain-promoted reactivity of a fluorene-derived [6]cycloparaphenyleneacetylene carbon nanohoop

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Selective strain-promoted reactivity of a fluorene-derived [6]cycloparaphenyleneacetylene carbon nanohoop

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