Supramolecular Gel Impede Oxygen Permeation and Foster Air-Sensitive Intermolecular Dearomative [4+2] Cycloaddition
Surajit Singh1, Pramod Rai1, Debasish Haldar1
1Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal, 741246, India.
Abstract:
The dearomative cycloaddition reaction provides a framework for transforming flat aromatic compounds into sp3-rich 3D molecular structures. Nonetheless, the instability of the triplet excited state of the photocatalyst and substrates in the presence of triplet quencher oxygen has so far necessitated an oxygen-free environment. Here, in this study, we illustrate that efficient intermolecular dearomative [4+2] cycloaddition via visible light energy-transfer catalysis can be conducted in the presence of air by employing readily assembled organogel networks as reaction platforms, producing outcomes akin to those under inert conditions. However, these reactions are completely suppressed in a homogeneous solution exposed to air. Our design has enabled the triplet-sensitized chemical reactions, confined within the segregated solvent pools amidst the nanofibers under aerobic conditions.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: Overview
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Thermal and Photochemical Electrocyclic Reactions: Overview


![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)