Organic Chemistry

Systems Chemistry across Multiple Length Scales: Macroscopic Flow via Dissipative Co-Assemblies Featuring Transient Amides



Fueled chemical systems have considerable functional potential that is still largely unexplored. Here, we report a new approach to transient amide bond formation and use it to harness chemical energy and convert it to mechanical motion by integrating dissipative self-assembly and the Marangoni effect in a source-sink system. Droplets are formed through dissipative self-assembly following the reaction of octylamine with 2,3-dimethylmaleic anhydride. The resulting amides are hydrolytically labile making the droplets transient, which allows them to act as a source of octylamine. A sink for octylamine was created by placing a drop of oleic acid on the air-water interface. This source – sink system sets up a gradient in surface tension, which gives rise to a macroscopic Marangoni flow that can transport the droplets in solution with tunable speed. Carbodiimides can fuel this motion by converting diacid waste back to anhydride. This study shows how fueling at the molecular level can, via assembly at the supramolecular level, lead to liquid flow at the macroscopic level.


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Supplementary material

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Supporting information
Description of materials and methods; supplementary figures and Python code for the computation model.
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Supporting videos
Zip file containing supporting videos 1-15