The Power of Action Plots: Unveiling Reaction Selectivity of Light-Stabilized Dynamic Covalent Chemistry |
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Authors: | Steven C. Gauci Prof. Filip E. Du Prez Dr. Joshua O. Holloway Dr. Hannes A. Houck Prof. Christopher Barner-Kowollik |
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Affiliation: | 1. School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George Street, QLD 4000 Brisbane, Australia;2. Department of Organic and Macromolecular Chemistry, Ghent University, Campus Sterre, Krijgslaan 281 S4-bis, 9000 Ghent, Belgium;3. Department of Chemistry and Institute of Advanced Study, University of Warwick, Library Road, Coventry, CV4 7AL UK |
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Abstract: | 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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Keywords: | Action Plot Analysis Dynamic Covalent Chemistry Light-Stabilized Dynamic Materials Wavelength-Dependent Reactivity |
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