Site-selective chemical reactions by on-water surface sequential assembly
Research output: Contribution to journal › Research article › Contributed › peer-review
Contributors
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.
Details
Original language | English |
---|---|
Article number | 8313 |
Journal | Nature communications |
Volume | 14 |
Issue number | 1 |
Publication status | Published - Dec 2023 |
Peer-reviewed | Yes |
External IDs
PubMed | 38097633 |
---|---|
ORCID | /0000-0001-5873-8751/work/151437430 |
ORCID | /0000-0002-8487-0972/work/151437665 |