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Molecular-scale dissipative chemistry drives the formation of nanoscale assemblies and their macroscale transport

Nature Chemistry volume 17, pages 124–131 (2025)Cite this article

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Abstract

Fuelled chemical systems have considerable functional potential that remains largely unexplored. Here we report an 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 enables them to act as a source of octylamine. A sink for octylamine was created by placing a drop of oleic acid at 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 fuelling at the molecular level can, via assembly at the supramolecular level, lead to liquid flow at the macroscopic level.

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Fig. 1: Chemically fuelled droplet formation and Marangoni convection.
Fig. 2: Droplet characterization and evidence for autopoiesis.
Fig. 3: Transient droplet formation without and with chemical fuelling.
Fig. 4: Chemically sustained Marangoni flow.

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Data availability

The UPLC data reported and analysed in this Article and its Supplementary Information are in the form of integrated peak areas and exported traces of representative chromatograms. All of the underlying chromatograms are stored locally in their native format. Owing to the large number of files, these are not provided with the supporting material but are available from the authors upon reasonable request. Source data are provided with this paper.

Code availability

The python code for the model is provided in the Supplementary Information.

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Acknowledgements

We thank N. Katsonis, A. Ryabchun and D. Babu for helpful discussion and V. V. Krasnikov for performing the confocal experiments. This work was supported by the Dutch Ministry of Education, Culture and Science Gravitation program 024.001.035 (S.O.), the oLife Cofund program (A.W.P.B.), the ERC AdG 741774 (S.O.), the China Scholarship Council (J.W.) and a Marie Curie Individual Fellowship for K.L. (PSR 786350).

Author information

Authors and Affiliations

  1. Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen, China

    Kai Liu

  2. Centre for Systems Chemistry, Stratingh Institute, University of Groningen, Groningen, the Netherlands

    Alex W. P. Blokhuis, Sietse J. Dijt, Juntian Wu, Shana Hamed, Armin Kiani, Bartosz M. Matysiak & Sijbren Otto

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Contributions

S.O., K.L. and B.M.M. conceived and designed the project. K.L. performed the experiments and analysed the data. A.W.P.B., S.J.D. and S.H. performed the hydrodynamic modelling. J.W. performed some MS, dynamic light scattering and UPLC experiments. A.K. carried out the cryo-TEM and TEM experiments. All authors participated in the discussions. K.L. and S.O. wrote the paper.

Corresponding authors

Correspondence to Kai Liu or Sijbren Otto.

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Nature Chemistry thanks Scott Hartley and Nishant Singh for their contribution to the peer review of this work.

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Supplementary information

Supplementary Information

Supplementary Figs. 1–39 and Table 1.

Supplementary Video 1

The initial movement of amide-based droplets in a source–sink system prepared using 35 mM 1a (pH 8.2).

Supplementary Video 2

The initial movement of amide-based droplets in a source–sink system prepared using 35 mM 1b (pH 8.2).

Supplementary Video 3

The initial movement of amide-based droplets in a source–sink system prepared using 45 mM 1a (pH 8.2).

Supplementary Video 4

The initial movement of amide-based droplets in a source–sink system prepared using 35 mM 1a (pH 8.8).

Supplementary Video 5

The movement of the droplets in Supplementary Video 1 upon prolonged observation.

Supplementary Video 6

The movement of the droplets in Supplementary Video 5 when new oleic acid was added.

Supplementary Video 7

The movement of polystyrene microspheres when the amides are all hydrolysed in Supplementary Video 5.

Supplementary Video 8

The initial movement of polystyrene microspheres when oleic acid was placed on an aqueous solution containing 2.

Supplementary Video 9

The movement of polystyrene microspheres in Supplementary Video 8 upon prolonged observation.

Supplementary Video 10

The initial movement of amide-based droplets in a source–sink system prepared using 45 mM 1a (pH 8.2) before fuelling with EDC-HCl.

Supplementary Video 11

The initial movement of the droplets in Supplementary Video 10 when EDC-HCl and oleic acid were added.

Supplementary Video 12

The initial movement of amide-based droplets in a source–sink system prepared using 45 mM 1a (pH 8.2) after the second addition of EDC-HCl fuel.

Supplementary Video 13

The initial movement of amide-based droplets in a source–sink system prepared using 45 mM 1a (pH 8.2) after the third addition of EDC-HCl fuel.

Supplementary Video 14

The initial movement of amide-based droplets in a source–sink system prepared using 45 mM 1a (pH 8.2) after the fourth addition of EDC-HCl fuel.

Supplementary Video 15

The initial movement of amide-based droplets in a source–sink system prepared using 45 mM 1a (pH 8.2) after the fifth addition of EDC-HCl fuel.

Supplementary Video 16

The initial movement of amide-based droplets that had almost completely hydrolysed in a source–sink system prepared using 45 mM 1a (pH 8.2) after new oleic acid was added.

Supplementary Video 17

The initial movement of amide-based droplets that had almost completely hydrolysed in a source–sink system prepared using 45 mM 1a (pH 8.2) after EDC-HCl was re-added.

Supplementary Code 1

Code for modelling the Marangoni flow.

Supplementary Data 1

Source data for Supplementary Figs. 6, 14, 15, 16, 17, 20, 21, 22, 24, 25, 27, 28, 31, 32, 34, 35, 36 and 39.

Source data

Source Data Fig. 2

Raw dynamic light scattering data; raw spectral data; absolute UPLC peak areas and the component concentration.

Source Data Fig. 3

Time-dependent spectral data; time-dependent size data; absolute UPLC peak areas and the component concentration.

Source Data Fig. 4

Raw modelling data; raw speed data.

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Liu, K., Blokhuis, A.W.P., Dijt, S.J. et al. Molecular-scale dissipative chemistry drives the formation of nanoscale assemblies and their macroscale transport. Nat. Chem. 17, 124–131 (2025). https://doi.org/10.1038/s41557-024-01665-z

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