Starazo triple switches - synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes.
Beilstein J Org Chem
; 16: 22-31, 2020.
Article
em En
| MEDLINE
| ID: mdl-31976013
ABSTRACT
Multistate switches allow to drastically increase the information storage capacity and complexity of smart materials. In this context, unsymmetrical 1,3,5-tris(arylazo)benzenes - 'starazos' - which merge three photoswitches on one benzene ring, were successfully prepared. Two different synthetic strategies, one based on Baeyer-Mills reactions and the other based on Pd-catalyzed coupling reactions of arylhydrazides and aryl halides, followed by oxidation, were investigated. The Pd-catalyzed route efficiently led to the target compounds, unsymmetrical tris(arylazo)benzenes. These triple switches were preliminarily characterized in terms of their isomerization behavior using UV-vis and 1H NMR spectroscopy. The efficient synthesis of this new class of unsymmetrical tris(arylazo)benzenes opened new avenues to novel multistate switching materials.
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MEDLINE
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En
Ano de publicação:
2020
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Article