Action Plots in Action: In-Depth Insights into Photochemical Reactivity
Description
Predicting wavelength-dependent photochemical reactivity is challenging. Herein, we revive the well-established tool of measuring action spectra and adapt the technique to map wavelength-resolved covalent bond formation and cleavage in what we term "photochemical action plots". Underpinned by tunable lasers, which allow excitation of molecules with near-perfect wavelength precision, the photoinduced reactivity of several reaction classes have been mapped in detail. These include photoinduced cycloadditions and bond formation based on photochemically generated o-quinodimethanes and 1,3-dipoles such as nitrile imines as well as radical photoinitiator cleavage. Organized by reaction class, these data demonstrate that UV/vis spectra fail to act as a predictor for photochemical reactivity at a given wavelength in most of the examined reactions, with the photochemical reactivity being strongly red shifted in comparison to the absorption spectrum. We provide an encompassing perspective of the power of photochemical action plots for bond-forming reactions and their emerging applications in the design of wavelength-selective photoresists and photoresponsive soft-matter materials.
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| ID Code: | 227330 | ||||||||
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| Item Type: | Contribution to Journal (Journal Article) | ||||||||
| Refereed: | Yes | ||||||||
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| Additional Information: | Funding Information: C.B.-K. acknowledges funding from the Australian Research Council (ARC) in the form of a Laureate Fellowship (FL170100014) enabling his photochemical research program as well as continued key support from the Queensland University of Technology (QUT). C.B.-K., J.P.B., and M.W. acknowledge additional support via an ARC Discovery grant targeted at red-shifting photoligation chemistry. I.M.I. gratefully acknowledges QUT for a Ph.D. Research Scholarship. H.F. acknowledges support by the ARC in the form of a DECRA Fellowship DE200101096). M.W. and C.B.-K. acknowledge additional funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany’s Excellence Strategy for the Excellence Cluster “3D Matter Made to Order” (EXC-2082/1-390761711), by the Carl Zeiss Foundation, and by the Helmholtz program “Materials Systems Engineering”. The authors thank Prof. Andreas Unterreiner (KIT) for helpful discussions during the revision process of this article. | ||||||||
| Measurements or Duration: | 14 pages | ||||||||
| DOI: | 10.1021/jacs.1c09419 | ||||||||
| ISSN: | 0002-7863 | ||||||||
| Pure ID: | 103968654 | ||||||||
| Divisions: | Current > Research Centres > Centre for Materials Science Current > Research Centres > Centre for a Waste Free World Current > QUT Faculties and Divisions > Faculty of Science Current > Schools > School of Chemistry & Physics |
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| Funding Information: | C.B.-K. acknowledges funding from the Australian Research Council (ARC) in the form of a Laureate Fellowship (FL170100014) enabling his photochemical research program as well as continued key support from the Queensland University of Technology (QUT). C.B.-K., J.P.B., and M.W. acknowledge additional support via an ARC Discovery grant targeted at red-shifting photoligation chemistry. I.M.I. gratefully acknowledges QUT for a Ph.D. Research Scholarship. H.F. acknowledges support by the ARC in the form of a DECRA Fellowship DE200101096). M.W. and C.B.-K. acknowledge additional funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany’s Excellence Strategy for the Excellence Cluster “3D Matter Made to Order” (EXC-2082/1-390761711), by the Carl Zeiss Foundation, and by the Helmholtz program “Materials Systems Engineering”. The authors thank Prof. Andreas Unterreiner (KIT) for helpful discussions during the revision process of this article. | ||||||||
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| Copyright Owner: | 2021 American Chemical Society | ||||||||
| Copyright Statement: | This work is covered by copyright. Unless the document is being made available under a Creative Commons Licence, you must assume that re-use is limited to personal use and that permission from the copyright owner must be obtained for all other uses. If the document is available under a Creative Commons License (or other specified license) then refer to the Licence for details of permitted re-use. It is a condition of access that users recognise and abide by the legal requirements associated with these rights. If you believe that this work infringes copyright please provide details by email to qut.copyright@qut.edu.au | ||||||||
| Deposited On: | 11 Jan 2022 02:51 | ||||||||
| Last Modified: | 25 Jul 2024 22:11 |
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