Issue 2, 2020

Exploiting the versatile alkyne-based chemistry for expanding the applications of a stable triphenylmethyl organic radical on surfaces

Abstract

The incorporation of terminal alkynes into the chemical structure of persistent organic perchlorotriphenylmethyl (PTM) radicals provides new chemical tools to expand their potential applications. In this work, this is demonstrated by the chemical functionalization of two types of substrates, hydrogenated SiO2-free silicon (Si–H) and gold, and, by exploiting the click chemistry, scarcely used with organic radicals, to synthesise multifunctional systems. On one hand, the one-step functionalization of Si–H allows a light-triggered capacitance switch to be successfully achieved under electrochemical conditions. On the other hand, the click reaction between the alkyne-terminated PTM radical and a ferrocene azide derivative, used here as a model azide system, leads to a multistate electrochemical switch. The successful post-surface modification makes the self-assembled monolayers reported here an appealing platform to synthesise multifunctional systems grafted on surfaces.

Graphical abstract: Exploiting the versatile alkyne-based chemistry for expanding the applications of a stable triphenylmethyl organic radical on surfaces

Supplementary files

Article information

Article type
Edge Article
Submitted
06 9 2019
Accepted
19 11 2019
First published
20 11 2019
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., 2020,11, 516-524

Exploiting the versatile alkyne-based chemistry for expanding the applications of a stable triphenylmethyl organic radical on surfaces

J. A. de Sousa, F. Bejarano, D. Gutiérrez, Y. R. Leroux, E. M. Nowik-Boltyk, T. Junghoefer, E. Giangrisostomi, R. Ovsyannikov, M. B. Casu, J. Veciana, M. Mas-Torrent, B. Fabre, C. Rovira and N. Crivillers, Chem. Sci., 2020, 11, 516 DOI: 10.1039/C9SC04499J

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