Synthesis of 4&prime;-alkoxy-4-(&omega;-cinnamoylalkoxy)azobenzenes and their photoswitchable behavior

Published: 14 November 2021 by MDPI in The 25th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-25-11685

Abstract:

In search of new thermotropic, photoswitchable materials, a number of 4′-alkoxy-4-(ω-cinnamoylalkoxy)azobenzenes were prepared. The synthetic procedure included O-alkylation of 4-nitrophenol, followed by reduction of the nitro group (H₂, Pd/C), diazotization of the aniline and subsequent reaction with ω-hydroxyalkoxybenzenes, followed by a modified Appel-type esterification (BrCCl₃, PPh₃). The photochemical behavior of the substances was investigated.

Keywords: trans-cis photoisomerisation, cinnamates; modified Appel-type reaction; azobenzenes

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Abdullah Al-Hemyari

Muna Bufaroosha

Thies Thiemann