Unsymmetric bistable [c2]daisy chain rotaxanes which combine two types of electroactive stoppers

Autor: Wolf, Adrian, Cid, Juan-José, Moulin, Emilie, Niess, Frédéric, Du, Guangyan, Goujon, Antoine, Busseron, Eric, Ruff, Adrian, Ludwigs, Sabine, Giuseppone, Nicolas
Přispěvatelé: Institut Charles Sadron (ICS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Universität Stuttgart [Stuttgart], Ruhr University Bochum (RUB), Moulin, Emilie
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: European Journal of Organic Chemistry
European Journal of Organic Chemistry, 2019, 2019 (21), pp.3421-3432. ⟨10.1002/ejoc.201900179⟩
ISSN: 1434-193X
1099-0690
Popis: International audience; Mechanically interlocked molecules (MIMs) have emerged as intriguing building blocks for the construction of stimuli-responsive devices and materials. A particularly interesting and well-implemented subclass of MIMs is composed of symmetric bistable [c2]daisy chain rotaxanes. Topologically, they consist in the double thread of two symmetric macrocycles that are covalently linked to an axle bearing two switchable stations and a bulky stopper to avoid unthreading. Here we report the synthesis and characterization of a series of unsymmetric bistable [c2]daisy chain rotaxanes that present two different electroactive units as stoppers (an electron donor triarylamine and an electron acceptor perylene bisimide unit). Using a combination of 1D and 2D NMR along with cyclic voltammetry, we demonstrate that the pH actuation of the mechanical bond can be used to modulate the electrochemical properties of the bistable [c2]daisy chain rotaxanes when switching between the contracted and extended forms. pH-Switchable [c2]daisy chain rotaxanes that present two different electroactive units as stoppers have been synthesized and fully characterized. Their actuation between the contracted and extended forms leads to a modification of their electrochemical properties.
Databáze: OpenAIRE
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