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Unraveling the Photoswitching Mechanism in Donor–Acceptor Stenhouse Adducts
Open accessAbstract
Molecular photoswitches have opened up a myriad of opportunities in applications ranging from responsive materials and control of biological function to molecular logics. Here, we show that the photoswitching mechanism of donor-acceptor Stenhouse adducts (DASA), a recently reported class of photoswitches, proceeds by photoinduced Z-E isomerization, followed by a thermal, conrotatory 4π-electrocyclization. The photogenerated intermediate is manifested by a bathochromically shifted band in the visible absorption spectrum of the DASA. The identification of the role of this intermediate reveals a key step in the photoswitching mechanism that is essential to the rational design of switching properties via structural modification.
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Cited by
Molecular photoswitches in aqueous environments
Volarić, J., Szymanski, W., Simeth, N. A., & Feringa, B. L. (2021) · Chemical Society Reviews · doi:10.1039/d0cs00547a · Cited by 438
Self-citationVisible light—responsive drug delivery nanoparticle via donor–acceptor stenhouse adducts (DASA)
Yap, J. E., Zhang, L., Lovegrove, J. T., Beves, J. E., & Stenzel, M. H. (2020) · Macromolecular Rapid Communications · doi:10.1002/marc.202000236 · Cited by 60
Metadata
- Authors
- Lerch, M. M., Wezenberg, S. J., Szymanski, W., & Feringa, B. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-05-10
- Volume
- 138
- Issue
- 20
- Pages
- 6344-6347
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2347161797
- Cited by
- 179
- References
- 0
- FWCI
- 8.44
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Unraveling the Photoswitching Mechanism in Donor–Acceptor Stenhouse Adducts. https://app.cochat.ai/papers/10.1021/jacs.6b01722
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- Lerch, M. M., Wezenberg, S. J., Szymanski, W., & Feringa, B. L. (2016). Unraveling the Photoswitching Mechanism in Donor–Acceptor Stenhouse Adducts. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.6b01722
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
