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A New Class of Rigid Multi(azobenzene) Switches Featuring Electronic Decoupling: Unravelling the Isomerization in Individual Photochromes
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4529468
Author(s) Galanti, Agostino; Santoro, Jasmin; Mannancherry, Rajesh; Duez, Quentin; Diez-Cabanes, Valentin; Valasek, Michal; De Winter, Julien; Cornil, Jerome; Gerbaux, Pascal; Mayor, Marcel; Samori, Paolo
Author(s) at UniBasel Mayor, Marcel
Mannancherry, Rajesh
Year 2019
Title A New Class of Rigid Multi(azobenzene) Switches Featuring Electronic Decoupling: Unravelling the Isomerization in Individual Photochromes
Journal Journal of the American Chemical Society
Volume 141
Number 23
Pages / Article-Number 9273-9283
Abstract We report a novel class of star-shaped multiazobenzene photoswitches comprising individual photochromes connected to a central trisubstituted 1,3,5-benzene core. The unique design of such C3-symmetric molecules, consisting of conformationally rigid and pseudoplanar scaffolds, made it possible to explore the role of electronic decoupling in the isomerization of the individual azobenzene units. The design of our tris-, bis-, and mono(azobenzene) compounds limits the ÏEuro-conjugation between the switches belonging to the same molecule, thus enabling the efficient and independent isomerization of each photochrome. An in-depth experimental insight by making use of different complementary techniques such as UVâEuro"vis absorption spectroscopy, high performance liquid chromatography, and advanced mass spectrometry methods as ion mobility revealed an almost complete absence of electronic delocalization. Such evidence was further supported by both experimental (electrochemistry, kinetical analysis) and theoretical (DFT calculations) analyses. The electronic decoupling provided by this molecular design guarantees a remarkably efficient photoswitching of all azobenzenes, as evidenced by their photoisomerization quantum yields, as well as by the Z-rich UV photostationary states. Ion mobility mass spectrometry was exploited for the first time to study multiphotochromic compounds revealing the occurrence of a large molecular shape change in such rigid star-shaped azobenzene derivatives. In view of their high structural rigidity and efficient isomerization, our multiazobenzene photoswitches can be used as key components for the fabrication of complex stimuli-responsive porous materials.
Publisher American Chemical Society
ISSN/ISBN 0002-7863 ; 1520-5126
URL https://doi.org/10.1021/jacs.9b02544
edoc-URL https://edoc.unibas.ch/75495/
Full Text on edoc No
Digital Object Identifier DOI 10.1021/jacs.9b02544
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/31091876
ISI-Number 000475540800024
Document type (ISI) Journal Article
 
   

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29/03/2024