Regioselective photocycloaddition for light-stabilised dynamic materials design

Exploiting the optimum wavelength of reactivity for efficient photochemical reactions has been well‐established based on the development of photochemical action plots. We herein demonstrate the power of such action plots by a remarkable example of the wavelength‐resolved photochemistry of two triazolinedione (TAD) substrates, i.e., aliphatic and aromatic substituted, that exhibit near identical absorption spectra yet possess vastly disparate photoreactivity. We present our findings in carefully recorded action plots, from which reaction selectivity is identified. The profound difference in photoreactivity is exploited by designing a ‘hybrid’ bisfunctional TAD molecule, enabling the formation of a dual‐gated reaction manifold that demonstrates the exceptional and site‐selective (photo)chemical behavior of both TAD substrates within a single small molecule.

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Die Stärke von Action Plots: Untersuchung der Reaktionsselektivität lichtstabilisierter dynamischer kovalenter Chemie

Gauci

Prez

Holloway

et al. 2023

Angewandte Chemie

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The Power of Action Plots: Unveiling Reaction Selectivity of Light‐Stabilized Dynamic Covalent Chemistry

et al. 2023

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The effect of different cyclic substituents on the properties of recyclable acetal-containing epoxy resins

Toendepi,

Zhu,

Liu

et al. 2024

Polymer

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Regioselective photocycloaddition for light-stabilised dynamic materials design

Abstract: The exact molecular network connectivity in dynamic polymer networks greatly impacts material properties and reprocessing conditions. While endo/exo stereoisomer effects of thermoreversible cycloaddition reactions (e.g. furan/maleimide) are well known to...

Cited by 3 publications

References 60 publications

Die Stärke von Action Plots: Untersuchung der Reaktionsselektivität lichtstabilisierter dynamischer kovalenter Chemie

Die Stärke von Action Plots: Untersuchung der Reaktionsselektivität lichtstabilisierter dynamischer kovalenter Chemie

The Power of Action Plots: Unveiling Reaction Selectivity of Light‐Stabilized Dynamic Covalent Chemistry

The effect of different cyclic substituents on the properties of recyclable acetal-containing epoxy resins

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