Foldamers in pseudo[2]rotaxanes and [2]rotaxanes: tuning the switching kinetics and metastability |
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| Authors: | Kang-Da Zhang Xin Zhao Gui-Tao Wang Yi Liu Ying Zhang Hao-Jie Lu Xi-Kui Jiang Zhan-Ting Li |
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| Institution: | 1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China;2. The Molecular Foundry, Lawrence Berkeley National Laboratory, One Cyclotron Road, Berkeley, CA 94720, USA;3. Chemistry of Department, Fudan University, 220 Handan Road, Shanghai 200433, China |
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| Abstract: | Hydrogen bonded arylamide foldamers have been introduced in switchable pseudo2]rotaxanes and 2]rotaxanes, which also include a cyclobisparaquat(p-phenylene) (CBPQT4+) ring and a ‘dumbbell’ containing tetrathiafulvalene (TTF) and 1,5-dioxynaphthalene (DNP, for rotaxanes). The foldamer size changes through folding and unfolding serve as a steric handle to modulate the mechanical movement of the CBPQT4+ ring along the dumbbell of the pseudo2]rotaxanes and 2]rotaxanes. By varying the number of the repeating units in the foldamer, the kinetics of the solvent-dependent slippage/deslippage of pseudo2]rotaxanes and the switching of the ring between TTF and DNP of the 2]rotoxanes can be tuned remarkably, with the time scope ranging from several minutes to several days, in twelve solvents of varying polarity, which have been confirmed by the 1H NMR, UV–vis spectroscopy, and cyclic voltammogram experiments. |
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