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Unsymmetric Bistable [ c 2]Daisy Chain Rotaxanes which Combine Two Types of Electroactive Stoppers
Author(s) -
Wolf Adrian,
Cid JuanJosé,
Moulin Emilie,
Niess Frédéric,
Du Guangyan,
Goujon Antoine,
Busseron Eric,
Ruff Adrian,
Ludwigs Sabine,
Giuseppone Nicolas
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900179
Subject(s) - daisy chain , bistability , perylene , rotaxane , materials science , cyclic voltammetry , covalent bond , supramolecular chemistry , molecule , electrochemistry , nanotechnology , chemistry , optoelectronics , computer science , organic chemistry , computer hardware , electrode
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 [ c 2]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 [ c 2]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 [ c 2]daisy chain rotaxanes when switching between the contracted and extended forms.