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首页> 外文期刊>Chemistry: A European journal >Evidence of Splitting 1,2,3-Triazole into an Alkyne and Azide by Low Mechanical Force in the Presence of Other Covalent Bonds
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Evidence of Splitting 1,2,3-Triazole into an Alkyne and Azide by Low Mechanical Force in the Presence of Other Covalent Bonds

机译：在存在其他共价键的情况下通过低机械力将1,2,3-三唑分解为炔和叠氮化物的证据

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摘要

The cycloaddition reaction of an alkyne and azide to form a 1,2,3-triazole is widely used in many areas. However, the stability of the triazole moiety under mechanical stress is unclear. To see if a triazole could be selectively split into an alkyne and azide in the presence of other typical covalent bonds, a mica surface functionalized with a molecule containing a triazole moiety in the middle and an activated ester at the end was prepared. An atomic force microscope (AFM) tip with amino groups on its surface was ramped over the mica surface at predefined locations, which could temporarily link the tip to the surface through amide bond formation. During retraction, the triazole or another bond in the linkage broke, and a force was recorded. The forces varied widely at different ramps from close to 0 pN to 860 pN due to nonspecific adhesions and to the inherent inconsistency of single bond rupture. If some of the forces were from triazole cycloreversion, there would be alkynes at the predefined ramping locations. The surface was reacted with an azide carboxylic acid followed by labeling with amino Au nanoparticles (AuNPs). AFM imaging revealed AuNPs at the predicted locations, which provided evidence that under certain conditions triazole could be split selectively in the presence of other bonds at forces below 860 pN.
机译：炔和叠氮化物的环加成反应形成1,2,3-三唑的方法广泛用于许多领域。但是，三唑部分在机械应力下的稳定性尚不清楚。为了观察在存在其他典型的共价键的情况下三唑是否可以选择性地拆分为炔烃和叠氮化物，制备了一种云母表面，该云母表面被中间含三唑部分的分子官能化并且末端具有活化的酯。在表面上带有氨基的原子力显微镜（AFM）尖端在预定位置在云母表面上倾斜，这可以通过形成酰胺键将尖端临时连接到表面。在缩回过程中，连接中的三唑或另一个键断裂，并记录了作用力。由于非特异性粘附和单键断裂固有的不一致，力在从接近0 pN到860 pN的不同斜率上变化很大。如果某些力来自三唑环还原，则在预定义的缓变位置处将存在炔烃。使表面与叠氮化物羧酸反应，然后用氨基Au纳米颗粒（AuNPs）标记。原子力显微镜成像揭示了在预测位置的金纳米粒子，这提供了证据，表明在某些条件下，三唑可以在860 pN以下的力作用下，在存在其他键的情况下选择性分裂。

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