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Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

Andreas H. Heindl and Hermann A. Wegner

Beilstein J. Org. Chem. 2020, 16, 22–31. https://doi.org/10.3762/bjoc.16.4

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Supporting Information File 1: Additional synthetic procedures, isomerization experiments, and ¹H/¹³C NMR spectra.
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Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

Andreas H. Heindl and Hermann A. Wegner

Beilstein J. Org. Chem. 2020, 16, 22–31. https://doi.org/10.3762/bjoc.16.4

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Heindl, A. H.; Wegner, H. A. Beilstein J. Org. Chem. 2020, 16, 22–31. doi:10.3762/bjoc.16.4

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TY  - JOUR
A1  - Heindl, Andreas H.
A1  - Wegner, Hermann A.
T1  - Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes
JF  - Beilstein Journal of Organic Chemistry
PY  - 2020///
VL  - 16
SP  - 22
EP  - 31
SN  - 1860-5397
DO  - 10.3762/bjoc.16.4
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.16.4
KW  - multistate photoswitches
KW  - synthesis
KW  - tris(arylazo)benzene
N2  - 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.
ER  -

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)