Work

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

Year: 2021

Type: article

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 chlo-ride-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 re-sulting 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.

Source: RSC Advances

DOI: 10.1039/d1ra04638a

Authors: Lisa Chen, Mona Arnold, Rémi Blinder, Fedor Jelezko, Alexander J. C. Kuehne

Institutions: Universität Ulm, DWI – Leibniz Institute for Interactive Materials

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,124

Funder: Deutsche Forschungsgemeinschaft