Related Experiment Video
Updated: Jul 2, 2025

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
Published on: March 4, 2021
2D Graphene Oxide Membrane Nanoreactors for Rapid Directional Flow Ring-Opening Reactions with Dominant
Jiangwei Fu1,2, Shuai Pang1,3, Yuhui Zhang1,3
1CAS Key Laboratory of Bio-Inspired Materials and Interfacial Science, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
Abstract:
Nanoconfinement within enzymes can increase reaction rate and improve selectivity under mild conditions. However, it remains a great challenge to achieve chemical reactions imitating enzymes with directional molecular motion, short reaction time, ≈100% conversion, and chiral conversion in artificial nanoconfined systems. Here, directional flow ring-opening reactions of styrene oxide and alcohols are demonstrated with ≈100% conversion in <120 s at 22 °C using graphene oxide membrane nanoreactors. Dominant products have the same configuration as chiral styrene oxide in confined reactions, which is dramatically opposed to bulk reactions. The unique chiral conversion mechanism is caused by spatial confinement, limiting the inversion of benzylic chiral carbon. Moreover, the enantiomeric excess of same-configuration products increased with higher alkyl charge in confined reactions. This work provides a new route to achieve rapid flow ring-opening reactions with specific chiral conversion within 2D nanoconfined channels, and insights into the impact of nanoconfinement on ring-opening reaction mechanisms.
Related Concept Videos
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Base-Catalyzed Ring-Opening of Epoxides
Acid-Catalyzed Ring-Opening of Epoxides
Thermal and Photochemical Electrocyclic Reactions: Overview
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

