The DOI matches its Crossref record; 83 of the 83 references it cites were found in a registry or an index.
A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor–Acceptor Cyanoarenes
Abstract
The targeted choice of specific photocatalysts has been shown to play a critical role for the successful realization of challenging photoredox catalytic transformations. Herein, we demonstrate the successful implementation of a rational design strategy for a series of deliberate structural manipulations of cyanoarene-based, purely organic donor-acceptor photocatalysts, using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a starting point. Systematic modifications of both the donor substituents as well as the acceptors' molecular core allowed us to identify strongly oxidizing as well as strongly reducing catalysts (e.g., for an unprecedented detriflation of unactivated naphthol triflate), which additionally offer remarkably balanced redox potentials with predictable trends. Especially halogen arene core substitutions are instrumental for our targeted alterations of the catalysts' redox properties. Based on their preeminent electrochemical and photophysical characteristics, all novel, purely organic photoredox catalysts were evaluated in three challenging, mechanistically distinct classes of benchmark reactions (either requiring balanced, highly oxidizing or strongly reducing properties) to demonstrate their enormous potential as customizable photocatalysts, that outperform and complement prevailing typical best photocatalysts.
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Cited by
Kwon, K., Simons, R. T., Nandakumar, M., & Roizen, J. L. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00444 · Cited by 389
Chmiel, A. F., Williams, O. P., Chernowsky, C. P., Yeung, C. S., & Wickens, Z. K. (2021) · Journal of the American Chemical Society · doi:10.1021/jacs.1c05988 · Cited by 281
Xu, J., Cao, J., Wu, X., Wang, H., Yang, X., Tang, X., Toh, R. W., Zhou, R., Yeow, E. K. L., & Wu, J. (2021) · Journal of the American Chemical Society · doi:10.1021/jacs.1c05994 · Cited by 280
Wu, C., Corrigan, N., Lim, C.-H., Liu, W., Miyake, G., & Boyer, C. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00409 · Cited by 259
Metadata
- Authors
- Speckmeier, E., Fischer, T. G., & Zeitler, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2018-10-02
- Volume
- 140
- Issue
- 45
- Pages
- 15353-15365
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2895247094
- Cited by
- 771
- References
- 83
- FWCI
- 19.35
- Type
- journal article
- Language
- en
- Open access
- closed
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- Speckmeier, E., Fischer, T. G., & Zeitler, K. (2018). A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor–Acceptor Cyanoarenes. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.8b08933
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