title: Light-controlled formation of vesicles and supramolecular organogels by a cholesterol-bearing amphiphilic molecular switch.
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.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (NL).
authors.forename: Jochem T
authors.initials: JT
authors.lastname: van Herpt
authors.forename: Jetsuda
authors.initials: J
authors.lastname: Areephong
authors.forename: Marc C A
authors.initials: MC
authors.lastname: Stuart
authors.forename: Wesley R
authors.initials: WR
authors.lastname: Browne
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D002784:Cholesterol / Q000737:chemistry*; D005782:Gels / Q000737:chemistry*; D008027:Light; D011092:Polyethylene Glycols / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D005782:Gels; D011725:Pyridines; D013501:Surface-Active Agents; D011092:Polyethylene Glycols; D002784:Cholesterol; C023666:pyridine
keywords: gels; molecular switches; photochromism; supramolecular chemistry; vesicles