Azobenzenes are among the most extensively used molecular switches. Due to the unique tunability of their (photo-)physical characteristics in combination with a high tolerance against photobleaching, azobenzenes can be found in many applications in all fields of photoswitching materials. However, sometimes, a major obstacle is the incorporation of azobenzenes into such systems, especially if a high yielding, fast and easy process is of paramount importance, for example for the postfunctionalization of polymers or peptides.<br/><br/>Here, we present a new synthetic approach to catalytically transform iodinated azobenzenes and diazocines into active <i>N</i>-hydroxysuccinimide (NHS) esters. Those active esters react selectively with primary amines under the formation of stable amide bonds making them a versatile tool for e.g. the crosslinking of peptides and proteins.

Active ester functionalized azobenzenes as versatile building blocks

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ACS Fall 2022

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