Issue 36, 2023

Synthesis and metalation of polycatechol nanohoops derived from fluorocycloparaphenylenes

Abstract

Due to their unique topology and distinct physical properties, cycloparaphenylenes (CPPs) are attractive building blocks for new materials synthesis. While both noncovalent interactions and irreversible covalent bonds have been used to link CPP monomers into extended materials, a coordination chemistry approach remains less explored. Here we show that nucleophilic aromatic substitution reactions can be leveraged to rapidly introduce donor groups (–OR, –SR) onto polyfluorinated CPP rings. Demethylation of methoxide-substituted CPPs produces polycatechol nanohoop ligands that are readily metalated to produce well-defined, multimetallic CPP complexes. As catechols are recurring motifs throughout coordination chemistry and dynamic covalent chemistry, the polycatechol nanohoops reported here open the door to new strategies for the bottom-up synthesis of atomically precise CPP-based materials.

Graphical abstract: Synthesis and metalation of polycatechol nanohoops derived from fluorocycloparaphenylenes

Supplementary files

Article information

Article type
Edge Article
Submitted
12 7 2023
Accepted
16 8 2023
First published
06 9 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 9724-9732

Synthesis and metalation of polycatechol nanohoops derived from fluorocycloparaphenylenes

A. A. Kamin, T. D. Clayton, C. E. Otteson, P. M. Gannon, S. Krajewski, W. Kaminsky, R. Jasti and D. J. Xiao, Chem. Sci., 2023, 14, 9724 DOI: 10.1039/D3SC03561A

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