Department of Chemical Engineering, Hanyang University, Seoul, Korea.
Department of Chemistry, Hanyang University, Seoul, Korea.
Nat Commun. 2021 Jul 9;12(1):4207. doi: 10.1038/s41467-021-24492-z.
Despite their great utility in synthetic and materials chemistry, Diels-Alder (DA) and retro Diels-Alder (rDA) reactions have been vastly unexplored in promoting self-assembly processes. Herein we describe the first example of a retro Diels-Alder (rDA) reaction-triggered self-assembly method. Release of the steric bulkiness associated with the bridged bicyclic DA adduct by the rDA reaction allowed generation of two building blocks that spontaneously self-assembled to form a supramolecular polymer. By employing photopolymerizable lipid building blocks, we demonstrated the efficiency of the rDA-based self-assembly strategy. Generation of reactive functional groups (maleimide and furan) that can be used for further modification of the supramolecular polymer is an additional meritorious feature of the rDA-based approach. Advantage was taken of reactive functional groups to fabricate stimulus-responsive selective and tunable colorimetric sensors. The strategy developed in this study should be useful for the design of systems that participate in triggered molecular assembly.
尽管 Diels-Alder（DA）和逆 Diels-Alder（rDA）反应在合成和材料化学中非常有用，但它们在促进自组装过程方面的应用却很少被探索。在此，我们描述了第一个逆 Diels-Alder（rDA）反应触发自组装方法的例子。rDA 反应释放与桥接双环 DA 加合物相关的空间位阻，从而生成两个构建块，这些构建块自发自组装形成超分子聚合物。通过使用光聚合脂质构建块，我们证明了基于 rDA 的自组装策略的效率。生成可用于进一步修饰超分子聚合物的反应性官能团（马来酰亚胺和呋喃）是基于 rDA 的方法的另一个优点。利用反应性官能团制造了对刺激具有响应性的选择性和可调谐比色传感器。本研究中开发的策略对于设计参与触发分子组装的系统应该是有用的。
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