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Dithienylethene optical switches. Multicomponent molecular systems

26 June 2009

PhD ceremony: J. Areephong, 14.45 uur, Academiegebouw, Broerstraat 5, Groningen

Thesis: Dithienylethene optical switches. Multicomponent molecular systems

Promotor(s): prof. B.L. Feringa

Faculty: Mathematics and Natural Sciences


Dithienylethenes are photochromic compounds that interconvert between two distinct states, between colorless open form and colored closed form when irradiation with ultraviolet and visible light, respectively. In this thesis, photochromic dithienylethene switching is employed to investigate multi-functional systems. The synthesis and photochemical characterization of a dithienylethene dimer covalently tethered by a short linker, -SiMe2-, is described as multi-switches for multi-addressable systems. Importantly, it was found that there is no significant intramolecular interaction between the two dithienylethene units despite theirs proximity.

Secondly, the photo- and electrochemical properties of self-assembled monolayers of diarylethenes on non-metallic surfaces (quartz and ITO surfaces) are investigated. The state of the modified surface can be read ‘non-destructively’ by electrochemical readout to achieve Read/Write/Erase information storage. 

Thirdly, the photochemical switching properties of dithienylethene compounds, which can be used to control the electropolymerization properties of bis-terthiophene monomer onto the surface with UV and visible light, respectively, is described. In the open state, electropolymerization yields alkene bridged sexithiophene polymers through oxidative a , a -coupling, while in the closed state the polymerizability is switched off. 

Moreover, the photoswitchable sexithiophene molecular wires were prepared by employing electrochemical dimerization of dithienylethene monomers. The photochromic dithienylethene units retain their photochemical properties when part of an extended p -conjugated sexithiophene system.

Finally, the syntheses of star-shaped dithienylethene substituted hexaphenylbenzenes through a dicobaltoctacarbonyl-catalyzed cyclotrimerization reaction. This reaction represents a direct facile method for the synthesis of hexaphenylbenzene centered multi-dithienylethene systems.


Last modified:15 September 2017 3.38 p.m.
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