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

    Year: 2023

    Journal: Nature Communications, Volume 14, 14/12/2023, page 8313

    Authors: Prasoon, Anupam; Yu, Xiaoqing; Hambsch, Mike; Bodesheim, David; Liu, Kejun; Zacarias, Angelica; Nguyen, Nguyen Ngan; Seki, Takakazu; Dianat, Aerzoo; Croy, Alexander; Cuniberti, Gianaurelio; Fontaine, Philippe; Nagata, Yuki; Mannsfeld, Stefan C. B.; Dong, Renhao; Bonn, Mischa; Feng, Xinliang

    Keywords: Self-assembly; Surface assembly; Organic molecules in materials science

    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.
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