Light-controlled orthogonal covalent bond formation at two different wavelengths
|
Accepted Version
(PDF 1MB)
33487226. Available under License Creative Commons Attribution Non-commercial 4.0. |
Description
We report light‐induced reactions in a two‐chromophore system capable of sequence‐independent λ‐orthogonal reactivity relying solely on the choice of wavelength and solvent. In a solution of water and acetonitrile, LED irradiation at λmax=285 nm leads to full conversion of 2,5‐diphenyltetrazoles with N‐ethylmaleimide to the pyrazoline ligation products. Simultaneously present o‐methylbenzaldehyde thioethers are retained. Conversely, LED irradiation at λmax=382 nm is used to induce ligation of the o‐methylbenzaldehydes in acetonitrile with N‐ethylmaleimide via o‐quinodimethanes, while 2,5‐diphenyltetrazoles also present are retained. This unprecedented photochemical selectivity is achieved through control of the number and wavelength of incident photons as well as favorable optical properties and quantum yields of the reactants in their environment.
Impact and interest:
Citation counts are sourced monthly from Scopus and Web of Science® citation databases.
These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.
Citations counts from the Google Scholar™ indexing service can be viewed at the linked Google Scholar™ search.
Full-text downloads:
Full-text downloads displays the total number of times this work’s files (e.g., a PDF) have been downloaded from QUT ePrints as well as the number of downloads in the previous 365 days. The count includes downloads for all files if a work has more than one.
| ID Code: | 132185 | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Item Type: | Contribution to Journal (Journal Article) | ||||||||
| Refereed: | Yes | ||||||||
| ORCID iD: |
|
||||||||
| Measurements or Duration: | 5 pages | ||||||||
| Keywords: | Acetonitrile, Chromophores, Irradiation, Light, Light emitting diodes, Optical properties, Orthogonality, Photochemical simulations, Tetrazoles, Wavelength-selective, chromatic orthogonality, photochemical simulation, photoenol, tetrazole, wavelength-selective photochemistry | ||||||||
| DOI: | 10.1002/anie.201901275 | ||||||||
| ISSN: | 1433-7851 | ||||||||
| Pure ID: | 33487226 | ||||||||
| Divisions: | Past > Institutes > Institute for Future Environments Past > QUT Faculties & Divisions > Science & Engineering Faculty |
||||||||
| Copyright Owner: | 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim | ||||||||
| 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: | 23 Aug 2019 03:12 | ||||||||
| Last Modified: | 18 Jul 2024 20:16 |
Export: EndNote | Dublin Core | BibTeX
Repository Staff Only: item control page