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![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)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Large and long-term photon energy storage in diazetidines via [2+2] photocycloaddition
Han P Q Nguyen1, Anurag Mukherjee1, Junichi Usuba1
1Department of Chemistry, Brandeis University 415 South Street Waltham MA 02453 USA gracehan@brandeis.edu.
Abstract:
We report a series of p-functionalized phenylbenzoxazoles that offer remarkable energy storage, exceeding 300 J g-1, for the first time among intermolecular cycloaddition-based molecular solar thermal energy storage systems. The [2 + 2] photocycloaddition of phenylbenzoxazoles generates diazetidine cycloadducts that store energy for up to 23 years in the solid state and release energy upon triggered cycloreversion. The solid-state phase transition contributes to increasing overall energy storage densities, and the dearomative cycloaddition process is revealed to be critical for maximizing the intrinsic energy storage capacities. The solvent-assisted cycloreversion is also used to accelerate the energy release from the emerging molecular scaffold.
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