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Electronic Decoupling in C3-Symmetrical Light-Responsive Tris(Azobenzene) Scaffolds: Self-Assembly and Multiphotochromism

Journal of the American Chemical Society, 2018-11, Vol.140 (47), p.16062-16070 [Peer Reviewed Journal]

Distributed under a Creative Commons Attribution 4.0 International License ;ISSN: 0002-7863 ;EISSN: 1520-5126 ;DOI: 10.1021/jacs.8b06324

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  • Title:
    Electronic Decoupling in C3-Symmetrical Light-Responsive Tris(Azobenzene) Scaffolds: Self-Assembly and Multiphotochromism
  • Author: Galanti, Agostino ; Diez-Cabanes, Valentin ; Santoro, Jasmin ; Valášek, Michal ; Minoia, Andrea ; Mayor, Marcel ; Cornil, Jérôme ; Samorì, Paolo
  • Subjects: Chemical Sciences ; Organic chemistry
  • Is Part Of: Journal of the American Chemical Society, 2018-11, Vol.140 (47), p.16062-16070
  • Description: We report the synthesis of a novel C3-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.
  • Publisher: American Chemical Society
  • Language: English
  • Identifier: ISSN: 0002-7863
    EISSN: 1520-5126
    DOI: 10.1021/jacs.8b06324
  • Source: Hyper Article en Ligne (HAL) (Open Access)
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