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A Perylene‐Bridged Switchable [3]Rotaxane Molecular Shuttle with a Fluorescence Output
Author(s) -
Cao ZhanQi,
Li Hong,
Yao Jian,
Zou Lei,
Qu DaHui,
Tian He
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402201
Subject(s) - rotaxane , chemistry , perylene , ferrocene , photoinduced electron transfer , photochemistry , molecular switch , chromophore , fluorescence , molecular machine , molecule , proton nmr , fluorescence spectroscopy , nuclear magnetic resonance spectroscopy , anthracene , fluorophore , spectroscopy , electron transfer , stereochemistry , nanotechnology , supramolecular chemistry , organic chemistry , materials science , physics , electrode , quantum mechanics , electrochemistry
Abstract A bistable bis‐branched [3]rotaxane with a perylene bisimide (PBI) chromophore that separates two mechanically interlocked [2]rotaxane arms including a diferrocene‐functionalized dibenzo‐24‐crown‐8 ring, was designed, prepared, and characterized by 1 H NMR and 13 C NMR spectroscopy and HR‐ESI mass spectrometry. The uniform relative shuttling movement of target [3]rotaxane in response to external acid‐base stimuli was confirmed by 1 H NMR spectroscopy. Furthermore, the shuttling motion of the macrocycles in the system was accompanied by a remarkably visual fluorescence change due to the distance‐dependent photoinduced electron transfer process from the ferrocene units to the PBI fluorophore. This kind of rotaxane has important potential for designing more sophisticated mechanically interlocked molecules with controllable functions.