Electronic Decoupling in C 3 -Symmetrical Light-Responsive Tris(Azobenzene) Scaffolds: Self-Assembly and Multiphotochromism

Electronic Decoupling in C 3 -Symmetrical Light-Responsive Tris(Azobenzene) Scaffolds: Self-Assembly and Multiphotochromism

We report the synthesis of a novel C -symmetrical multiphotochromic molecule bearing three azobenzene units at positions 1, 3, 5 of the central phenyl ring. The unique geometrical design of such a rigid scaffold enables the electronic decoupling of the azobenzene moieties to guarantee their simultan...

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Veröffentlicht in:Journal of the American Chemical Society 2018-11, Vol.140 (47), p.16062-16070
Hauptverfasser: Galanti, Agostino, Diez-Cabanes, Valentin, Santoro, Jasmin, Valášek, Michal, Minoia, Andrea, Mayor, Marcel, Cornil, Jérôme, Samorì, Paolo
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container_end_page 16070
container_issue 47
container_start_page 16062
container_title Journal of the American Chemical Society
container_volume 140
creator Galanti, Agostino
Diez-Cabanes, Valentin
Santoro, Jasmin
Valášek, Michal
Minoia, Andrea
Mayor, Marcel
Cornil, Jérôme
Samorì, Paolo
description We report the synthesis of a novel C -symmetrical multiphotochromic molecule bearing three azobenzene units at positions 1, 3, 5 of the central phenyl ring. The unique geometrical design of such a rigid scaffold enables the electronic decoupling of the azobenzene moieties to guarantee their simultaneous isomerization. Photoswitching of all azobenzenes in solution was demonstrated by means of UV-vis absorption spectroscopy and high performance liquid chromatography (HPLC) analysis. Scanning tunneling microscopy investigations at the solid-liquid interface, corroborated by molecular modeling, made it possible to unravel the dynamic self-assembly of such systems into ordered supramolecular architectures, by visualizing and identifying the patterns resulting from three different isomers, thereby demonstrating that the multiphotochromism is retained when the molecules are confined in two dimensions.
doi_str_mv 10.1021/jacs.8b06324
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title Electronic Decoupling in C 3 -Symmetrical Light-Responsive Tris(Azobenzene) Scaffolds: Self-Assembly and Multiphotochromism
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