Issue 44, 2021

Mixed-halide triphenyl methyl radicals for site-selective functionalization and polymerization

Abstract

Derivatives of the stable, luminescent tris-2,4,6-trichlorophenylmethyl (TTM) radical exhibit unique doublet spin properties that are of interest for applications in optoelectronics, spintronics, and energy storage. However, poor reactivity of the chloride-moieties limits the yield of functionalization and thus the accessible variety of high performance luminescent radicals. Here, we present a pathway to obtain mixed-bromide and chloride derivatives of TTM by simple Friedel–Crafts alkylation. The resulting radical compounds show higher stability and site-specific reactivity in cross-coupling reactions, due to the better leaving group character of the para-bromide. The mixed halide radicals give access to complex, and so far inaccessible luminescent open-shell small molecules, as well as polymers carrying the radical centers in their backbone. The new mixed-halide triphenyl methyl radicals represent a powerful building block for customized design and synthesis of stable luminescent radicals.

Graphical abstract: Mixed-halide triphenyl methyl radicals for site-selective functionalization and polymerization

Supplementary files

Article information

Article type
Paper
Submitted
15 Jun 2021
Accepted
09 Aug 2021
First published
13 Aug 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 27653-27658

Mixed-halide triphenyl methyl radicals for site-selective functionalization and polymerization

L. Chen, M. Arnold, R. Blinder, F. Jelezko and A. J. C. Kuehne, RSC Adv., 2021, 11, 27653 DOI: 10.1039/D1RA04638A

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements