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Synthetic Molecular Machine Based on Reversible End‐to‐Interior and End‐to‐End Loop Formation Triggered by Electrochemical Stimuli
Author(s) -
Lee Jae Wook,
Hwang Ilha,
Jeon Woo Sung,
Ko Young Ho,
Sakamoto Shigeru,
Yamaguchi Kentaro,
Kim Kimoon
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800054
Subject(s) - intramolecular force , viologen , electrochemistry , chemistry , electron transfer , molecule , dimer , electron transport chain , molecular machine , redox , electrode , photochemistry , nanotechnology , stereochemistry , materials science , inorganic chemistry , organic chemistry , biochemistry
We have designed and synthesized a novel [2]pseudorotaxane‐based molecular machine in which the interconversion between end‐to‐interior and end‐to‐end loop structures is reversibly controlled by electrochemical stimuli. Cucurbit[8]uril (CB[8]) and the thread molecule 3 4+ with an electron‐rich hydroxynaphthalene unit and two electron‐deficient viologen units form the 1:1 complex 4 4+ with an end‐to‐interior loop structure, which is reversibly converted into an end‐to‐end structure upon reduction. Large changes in shape and size of the molecule accompany the reversible redox process. The key feature of the machine‐like behavior is the reversible interconversion between an intramolecular charge‐transfer complex and viologen cation radical dimer inside CB[8] triggered by electrochemical stimuli.