Schock Marvin, Bräse Stefan
Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Institute of Biological and Chemical Systems-FMS (IBCS-FMS), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
Molecules. 2020 Feb 24;25(4):1009. doi: 10.3390/molecules25041009.
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.
叠氮基团的特殊反应活性使有机叠氮化物成为化学和材料科学中一类用途广泛的化合物。使用有机叠氮化物的最突出反应之一是区域选择性铜（I）催化的与炔烃的惠斯根1,3 - 偶极环加成反应，生成1,2,3 - 三唑。其他命名反应包括施陶丁格还原反应、氮杂维蒂希反应和库尔提斯重排反应。有机叠氮化物在材料科学中的受欢迎程度主要基于它们通过热活化或光解释放氮气的倾向。一方面，这种断裂反应伴随着大量的能量输出，使它们作为高能材料而备受关注。另一方面，它产生高活性的氮烯，在聚合物交联中表现出非凡的效率，聚合物交联是一种用于改变聚合物物理性质并提高基于聚合物的器件（如膜燃料电池、有机太阳能电池（OSC）、发光二极管（LED）和有机场效应晶体管（OFET））效率的过程。热固性材料也是合适的应用领域。在大多数情况下，使用具有多个叠氮功能的有机叠氮化物，它们可以是小分子或低聚物和聚合物。本综述重点关注多价有机叠氮化物在材料和生命科学中基于氮烯的应用。
