ArticleThe Journal of organic chemistry2022
How Robust Is the Reversible Steric Shielding Strategy for Photoswitchable Organocatalysts?
Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Overcoming the Pitfalls of Computing Reaction Selectivity from Ensembles of Transition States.The journal of physical chemistry letters · 2024Article
- Dithienylethene-Based Photoswitchable Phosphines for the Palladium-Catalyzed Stille Coupling Reaction.Inorganic chemistry · 2024Article
- From Organic Fragments to Photoswitchable Catalysts: The OFF-ON Structural Repository for Transferable Kernel-Based Potentials.Journal of chemical information and modeling · 2024Article
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Authors and funding
5 authors.
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No grant is acknowledged in the PubMed record.
Abstract
A highly appealing strategy to modulate a catalyst's activity and/or selectivity in a dynamic and noninvasive way is to incorporate a photoresponsive unit into a catalytically competent molecule. However, the description of the photoinduced conformational or structural changes that alter the catalyst's intrinsic reactivity is often reduced to a handful of intuitive static representations, which can struggle to capture the complexity of flexible organocatalysts. Here, we show how a comprehensive exploration of the free energy landscape of N-alkylated azobenzene-tethered piperidine catalysts is essential to unravel the conformational characteristics of each configurational state and explain the experimentally observed reactivity trends. Mapping the catalysts' conformational space highlights the existence of false ON or OFF states that lower their switching ability. Our findings expose the challenges associated with the realization of a reversible steric shielding for the photocontrol of Brønsted basicity of piperidine photoswitchable organocatalysts.
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