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- Title
Site-selective chemical reactions by on-water surface sequential assembly.
- 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
- 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. Controlling site-selectivity and reactivity in chemical reactions continues to be a key challenge in modern synthetic chemistry. Here, the authors demonstrate the assembly of amino-substituted porphyrins on a water surface into J-aggregate structures in the presence of charged surfactants.
- Subjects
CHEMICAL reactions; SURFACE reactions; ORGANIC chemistry; SURFACE structure; PORPHYRINS
- Publication
Nature Communications, 2023, Vol 14, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-023-44129-7