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Solid-State Synthesis and Structure of o- and p-Substituted Azobenzene Amides

Azobenzene derivatives are extensively exploited as molecular switches for biological and material science applications [1] and functional light- responsive materials [2]. Introducing azobenzene amide scaffolds into biomacromolecules, i.e. proteins [3] and nucleosides [4], have been utilized for controlling their structure, function, and interactions in vitro. Within this work, a mechanochemical synthesis of o- and p-substituted azobenzene amides with selected amino acid functionalities (Scheme 1) was developed. Optimization of the reaction conditions included a variation of milling jar’s and ball’s materials, type and quantity of the added base as well as testing the effect of the liquid additive (DMF) and/or the solid auxiliary (SiO2) on the reaction course. Mechanism of this reaction has been studied by in situ Raman spectroscopy and formation of the products was confirmed by NMR spectroscopy. The obtained amides were characterized by spectroscopic and crystallographic methods.

amides ; mechanochemistry ; azobenzenes

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