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Light‐Controlled [3]Pseudorotaxane Based on Tetrasulfonated 1,5‐Dinaphtho‐32‐Crown‐8 and α‐Cyclodextrin
Author(s) -
Wang Jun,
Zhang YingMing,
Zhang XuJie,
Zhao XiaoJun,
Liu Yu
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.201402238
Subject(s) - azobenzene , chemistry , cyclodextrin , pyridinium , photoisomerization , moiety , supramolecular chemistry , isomerization , crown ether , combinatorial chemistry , quinoline , photochemistry , stereochemistry , molecule , medicinal chemistry , organic chemistry , catalysis , ion
We developed the synthesis of a multicomponent molecular machine by employing the inclusion complex of an azobenzene‐containing pyridinium salt ( G1 ) with α‐cyclodextrin (α‐CD) and tetrasulfonated 1,5‐dinaphtho‐32‐crown‐8 (DNC) in water. The interconversion of the heterowheel trans ‐ G1⋅ DNC ⋅ α‐CD [3]pseudorotaxane into cis ‐ G1⋅ DNC [2]pseudorotaxane was modulated by the photoinduced isomerization of the azobenzene moiety accompanied by the release of α‐CD from the molecular axle. In control experiments, the azobenzene center of the bis(pyridinium)‐modified azobenzene ( G2 ) could not be isomerized in the presence of DNC and α‐CD. Only polymeric aggregates were obtained with the G2⋅ DNC ⋅ α‐CD system, which indicates that the inclusion complex with α‐CD and the electrostatic attraction with DNC are crucial to govern the reversible photoswitchable process. This work may provide a method to induce conformational changes of supramolecular assemblies that have multiple macrocyclic receptors.