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Light‐Controlled Formation of Vesicles and Supramolecular Organogels by a Cholesterol‐Bearing Amphiphilic Molecular Switch
Author(s) -
van Herpt Jochem T.,
Areephong Jetsuda,
Stuart Marc C. A.,
Browne Wesley R.,
Feringa Ben L.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302902
Subject(s) - amphiphile , supramolecular chemistry , ethylene glycol , vesicle , molecule , aqueous solution , pyridinium , chemistry , self assembly , lamellar structure , micelle , materials science , chemical engineering , polymer chemistry , nanotechnology , organic chemistry , copolymer , membrane , crystallography , polymer , biochemistry , engineering
Abstract A new responsive material composed of an amphiphilic light‐switchable dithienylethene unit functionalized with a hydrophobic cholesterol unit and a hydrophilic poly(ethylene glycol)‐modified pyridinium group has been designed. This unique single‐molecule system shows responsive light‐switchable self‐assembly in both water and organic solvents. Light‐triggered reversible vesicle formation in aqueous solutions is reported. The molecule shows a different behavior in apolar aromatic solvents, in which light‐controlled formation of organogel fibers is observed. The light‐triggered aggregation behavior of this molecule demonstrates that control of a supramolecular structure with light can be achieved in both aqueous and organic media and that this ability can be present in a single molecule. This opens the way toward the effective development of new strategies in soft nanotechnology for applications in controlled chemical release systems.