Site-selective chemical reactions by on-water surface sequential assembly

Anupam Prasoon, Xiaoqing Yu, Mike Hambsch, David Bodesheim, Kejun Liu, Angelica Zacarias, Nguyen Ngan Nguyen, Takakazu Seki, Aerzoo Dianat, Alexander Croy, Gianaurelio Cuniberti, Philippe Fontaine, Yuki Nagata, Stefan C. B. Mannsfeld (), Renhao Dong (), Mischa Bonn () and Xinliang Feng ()
Additional contact information
Anupam Prasoon: Technische Universität Dresden
Xiaoqing Yu: Max Planck Institute for Polymer Research
Mike Hambsch: Technische Universität Dresden
David Bodesheim: Technische Universität Dresden
Kejun Liu: Technische Universität Dresden
Angelica Zacarias: Max Planck Institute for Microstructure Physics
Nguyen Ngan Nguyen: Technische Universität Dresden
Takakazu Seki: Max Planck Institute for Polymer Research
Aerzoo Dianat: Technische Universität Dresden
Alexander Croy: Friedrich Schiller University Jena
Gianaurelio Cuniberti: Technische Universität Dresden
Philippe Fontaine: Synchrotron SOLEIL, L’Orme des Merisiers
Yuki Nagata: Max Planck Institute for Polymer Research
Stefan C. B. Mannsfeld: Technische Universität Dresden
Renhao Dong: Technische Universität Dresden
Mischa Bonn: Max Planck Institute for Polymer Research
Xinliang Feng: Technische Universität Dresden

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Controlling site-selectivity and reactivity in chemical reactions continues to be a key challenge in modern synthetic chemistry. Here, we demonstrate the discovery of site-selective chemical reactions on the water surface via a sequential assembly approach. A negatively charged surfactant monolayer on the water surface guides the electrostatically driven, epitaxial, and aligned assembly of reagent amino-substituted porphyrin molecules, resulting in a well-defined J-aggregated structure. This constrained geometry of the porphyrin molecules prompts the subsequent directional alignment of the perylenetetracarboxylic dianhydride reagent, enabling the selective formation of a one-sided imide bond between porphyrin and reagent. Surface-specific in-situ spectroscopies reveal the underlying mechanism of the dynamic interface that promotes multilayer growth of the site-selective imide product. The site-selective reaction on the water surface is further demonstrated by three reversible and irreversible chemical reactions, such as imide-, imine-, and 1, 3-diazole (imidazole)- bonds involving porphyrin molecules. This unique sequential assembly approach enables site-selective chemical reactions that can bring on-water surface synthesis to the forefront of modern organic chemistry.

Date: 2023
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DOI: 10.1038/s41467-023-44129-7

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