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

Cite this: J. Am. Chem. Soc. 2018, 140, 47, 16062–16070
Publication Date (Web):October 31, 2018
https://doi.org/10.1021/jacs.8b06324
Copyright © 2018 American Chemical Society
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    Abstract

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    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.

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