Microdroplet-Controlled Divergent Reactivity at a Gas-Organic Interface

23 August 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Gas-liquid Interface plays key roles in many fantastic phenomena due to specific properties. Although remarkable reactivities were benefited from gas-water interface of aqueous microdroplets, it remains unknown for gas-organic interface. This work discovers such extraordinary reactivity of gas-organic interface using organic microdroplets (acetonitrile and other organic solvents). This reactivity at the gas-organic interface facilitated a novel micrordroplet-controlled divergence, i.e., double C–N cleavage in high efficiency (yields > 90% in milliseconds) compared to single C–N bond breakdown and intramolecular cycloarrangement in bulk under harsher conditions from the same imidazolines. This study is not only important to wide applicability and inherent mechanisms of the gas-organic interface but also enables good insights into gas-water and other interface-rich studies in atmospheric and photochemistry, on-water chemistry, biological and biomedical, industrial, and energy.

Keywords

Gas-organic interface
interfacial effect
divergent reactivity
chemoselectivity
microdroplets
reaction acceleration
vicinal diamines
N-heterocycles

Supplementary materials

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Description
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Title
Supporting Information is available and includes 1H NMR spectra, 13C NMR spectra, high-resolution mass spectrometry (HRMS), High-performance liquid chromatography (HPLC) and Crystallographic data
Description
Supporting Information is available and includes 1H NMR spectra, 13C NMR spectra, high-resolution mass spectrometry (HRMS), High-performance liquid chromatography (HPLC) and Crystallographic data
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