Abstract
The exceptional reactivity of the azide group makes organic azides a highly versatile family of compounds in chemistry and the material sciences. One of the most prominent reactions employing organic azides is the regioselective copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition with alkynes yielding 1,2,3-triazoles. Other named reactions include the Staudinger reduction, the aza-Wittig reaction, and the Curtius rearrangement. The popularity of organic azides in material sciences is mostly based on their propensity to release nitrogen by thermal activation or photolysis. On the one hand, this scission reaction is accompanied with a considerable output of energy, making them interesting as highly energetic materials. On the other hand, it produces highly reactive nitrenes that show extraordinary efficiency in polymer crosslinking, a process used to alter the physical properties of polymers and to boost efficiencies of polymer-based devices such as membrane fuel cells, organic solar cells (OSCs), light-emitting diodes (LEDs), and organic field-effect transistors (OFETs). Thermosets are also suitable application areas. In most cases, organic azides with multiple azide functions are employed which can either be small molecules or oligo- and polymers. This review focuses on nitrene-based applications of multivalent organic azides in the material and life sciences.
Highlights
The characteristics of being explosive, malodorous, and highly volatile are usually adverse properties of a compound in the lab
This review focuses on nitrene-based applications of multivalent organic azides in the material and life sciences
The crosslinking density was lower at higher temperatures, probably due too side reactions resulting from an excess of reactive nitrene radicals as well as evaporation of the bisazide [84]
Summary
The characteristics of being explosive, malodorous, and highly volatile are usually adverse properties of a compound in the lab. The material’s mechanical properties, like solubility and hardness, are changed [3,4,5,6,7] In recent years, this process has proven to be a powerful strategy to boost efficiencies of polymer-based devices such as membrane fuel cells, organic solar cells (OSCs), light-emitting diodes (LEDs), and organic field-effect transistors (OFETs). Molecules 2020, 25, 1009 acceptor material in bulk hetero junction organic solar cells was successfully locked and the long-time stability of the device increased in this way [8] Due their superior crosslinking efficiency and mild activation methods devoid of the addition of initiators, organic azides have become the compounds of choice in these applications. Azido binders and plasticizers are considered as green materials, because combustion produces only molecular nitrogen and other non-toxic decomposition products
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