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

Jesús Alejandro de Sousa , Francesc Bejarano, Diego Gutiérrez, Yann Leroux, Ewa-Malgorzata Nowik Boltyk, Tobias Junghoefer, Erika Giangrisostomi, Ruslan Ovsyannikov, Maria Benedetta Casu, Jaume Veciana, Marta Mas-Torrent, Bruno Fabre, Concepció Rovira and Nuria Crivillers. Chem. Sci., 2019, Accepted Manuscript.  

DOI:10.1039/C9SC04499J

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

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

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