Self-assembly using a retro Diels-Alder reaction

Jaeyoung Park, Jung-Moo Heo, Sicheon Seong, Jaegeun Noh and Jong-Man Kim ()
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Jaeyoung Park: Hanyang University
Jung-Moo Heo: Hanyang University
Sicheon Seong: Hanyang University
Jaegeun Noh: Hanyang University
Jong-Man Kim: Hanyang University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract 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.

Date: 2021
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DOI: 10.1038/s41467-021-24492-z

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