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Tunable Visible and Near Infrared Photoswitches
Open accessAbstract
A class of tunable visible and near-infrared donor-acceptor Stenhouse adduct (DASA) photoswitches were efficiently synthesized in two to four steps from commercially available starting materials with minimal purification. Using either Meldrum's or barbituric acid "acceptors" in combination with aniline-based "donors", an absorption range spanning from 450 to 750 nm is obtained. Additionally, photoisomerization results in complete decoloration for all adducts, yielding fully transparent, colorless solutions and films. Detailed investigations using density functional theory, nuclear magnetic resonance, and visible absorption spectroscopies provide valuable insight into the unique structure-property relationships for this novel class of photoswitches. As a final demonstration, selective photochromism is accomplished in a variety of solvents and polymer matrices, a significant advantage for applications of this new generation of DASAs.
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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
Recent Implementations of Molecular Photoswitches into Smart Materials and Biological Systems
Pianowski, Z. L. (2019) · Chemistry – A European Journal · doi:10.1002/chem.201805814 · Cited by 328
Taking phototherapeutics from concept to clinical launch
Vickerman, B. M., Zywot, E. M., Tarrant, T. K., & Lawrence, D. S. (2021) · Nature Reviews Chemistry · doi:10.1038/s41570-021-00326-w · Cited by 201
Visible 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
Visible‐ and Near‐Infrared Light‐Driven Molecular Photoswitches for Biological Applications
Xu, Y., Tang, Y., & Li, Q. (2025) · Advanced Functional Materials · doi:10.1002/adfm.202416359 · Cited by 49
Metadata
- Authors
- Hemmer, J. R., Poelma, S. O., Treat, N., Page, Z. A., Dolinski, N. D., Diaz, Y. J., Tomlinson, W., Clark, K. D., Hooper, J. P., Hawker, C., & Read de Alaniz, J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-10-18
- Volume
- 138
- Issue
- 42
- Pages
- 13960-13966
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2528797353
- Cited by
- 280
- References
- 0
- FWCI
- 11.06
- Type
- journal article
- Language
- en
- Open access
- green
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- Hemmer, J. R., Poelma, S. O., Treat, N., Page, Z. A., Dolinski, N. D., Diaz, Y. J., Tomlinson, W., Clark, K. D., Hooper, J. P., Hawker, C., & Read de Alaniz, J. (2016). Tunable Visible and Near Infrared Photoswitches. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.6b07434
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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