Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 21, Pages 3421-3432Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900179
Keywords
Rotaxanes; Triarylamine; Perylene; PH-Responsive; Electroactive
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Funding
- international center for Frontier Research in Chemistry
- Agence Nationale pour la Recherche [ANR-09-BLAN-034-02]
- French Ministry of Research
- China Scholarship Council
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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. Herein 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.
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