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Issue 2, 2020
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Exploiting the versatile alkyne-based chemistry for expanding the applications of a stable triphenylmethyl organic radical on surfaces

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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

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Article information


Submitted
06 Sep 2019
Accepted
19 Nov 2019
First published
20 Nov 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 516-524
Article type
Edge Article

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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