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Mechanically gated formation of donor–acceptor Stenhouse adducts enabling mechanochemical multicolour soft lithography
Nature Chemistry ( IF 19.2 ) Pub Date : 2023-01-23 , DOI: 10.1038/s41557-022-01126-5
Anna C Overholts 1 , Wendy Granados Razo 1 , Maxwell J Robb 1
Affiliation  

Stress-sensitive molecules called mechanophores undergo productive chemical transformations in response to mechanical force. A variety of mechanochromic mechanophores, which change colour in response to stress, have been developed, but modulating the properties of the dyes generally requires the independent preparation of discrete derivatives. Here we introduce a mechanophore platform enabling mechanically gated multicolour chromogenic reactivity. The mechanophore is based on an activated furan precursor to donor–acceptor Stenhouse adducts (DASAs) masked as a hetero-Diels–Alder adduct. Mechanochemical activation of the mechanophore unveils the DASA precursor, and subsequent reaction with a secondary amine generates an intensely coloured DASA. Critically, the properties of the DASA are controlled by the amine, and thus a single mechanophore can be differentiated post-activation to produce a wide range of functionally diverse DASAs. We highlight this system by establishing the concept of mechanochemical multicolour soft lithography whereby a complex multicolour composite image is printed into a mechanochemically active elastomer through an iterative process of localized compression followed by reaction with different amines.



中文翻译:

供体-受体 Stenhouse 加合物的机械门控形成使机械化学多色软光刻成为可能

称为机械细胞的压力敏感分子会响应机械力而发生富有成效的化学转化。已经开发出多种响应于压力而改变颜色的机械变色机械细胞,但调节染料的性质通常需要独立制备离散衍生物。在这里,我们介绍了一种能够实现机械门控多色显色反应的机械平台。机械细胞基于活化的呋喃前体,供体-受体 Stenhouse 加合物 (DASA) 被掩盖为异狄尔斯-桤木加合物。机械载体的机械化学活化揭示了 DASA 前体,随后与仲胺的反应产生了强烈着色的 DASA。至关重要的是,DASA 的特性由胺控制,因此,单个机械细胞可以在激活后进行分化,以产生范围广泛的功能多样的 DASA。我们通过建立机械化学多色软光刻的概念来强调该系统,通过局部压缩的迭代过程,然后与不同的胺反应,将复杂的多色复合图像印刷到机械化学活性弹性体中。

更新日期:2023-01-23
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