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The photochemical ring-opening of 1,3-cyclohexadiene imaged by ultrafast electron diffraction
Open accessAbstract
The ultrafast photoinduced ring-opening of 1,3-cyclohexadiene constitutes a textbook example of electrocyclic reactions in organic chemistry and a model for photobiological reactions in vitamin D synthesis. Here, we present direct and unambiguous observation of the ring-opening reaction path on the femtosecond timescale and sub-{\AA}ngstr\"om length scale by megaelectronvolt ultrafast electron diffraction. We follow the carbon-carbon bond dissociation and the structural opening of the 1,3-cyclohexadiene ring by direct measurement of time-dependent changes in the distribution of interatomic distances. We observe a substantial acceleration of the ring-opening motion after internal conversion to the ground state due to steepening of the electronic potential gradient towards the product minima. The ring-opening motion transforms into rotation of the terminal ethylene groups in the photoproduct 1,3,5-hexatriene on the sub-picosecond timescale. Our work demonstrates the potential of megaelectronvolt ultrafast electron diffraction to elucidate photochemical reaction paths in organic chemistry.
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Citations
Cites
Femtosecond x-ray spectroscopy of an electrocyclic ring-opening reaction
Attar, A. R., Bhattacherjee, A., Pemmaraju, C. D., Schnorr, K., Closser, K. D., Prendergast, D., & Leone, S. R. (2017) · Science · doi:10.1126/science.aaj2198 · Cited by 338
Imaging Molecular Motion: Femtosecond X-Ray Scattering of an Electrocyclic Chemical Reaction
Minitti, M. P., Budarz, J. M., Kirrander, A., Robinson, J. S., Ratner, D., Lane, T. J., Zhu, D., Glownia, J. M., Kozina, M., Lemke, H. T., et al. (2015) · Physical Review Letters · doi:10.1103/physrevlett.114.255501 · Cited by 318
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Cited by
Seritan, S., Bannwarth, C., Fales, B. S., Hohenstein, E. G., Isborn, C. M., Kokkila‐Schumacher, S. I. L., Li, X., Liu, F., Luehr, N., Snyder, J. W., et al. (2021) · WIREs Computational Molecular Science · doi:10.1002/wcms.1494 · Cited by 312
Self-citationMultireference Electron Correlation Methods: Journeys along Potential Energy Surfaces
Park, J. W., Al-Saadon, R., MacLeod, M. K., Shiozaki, T., & Vlaisavljevich, B. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00496 · Cited by 155
Metadata
- Authors
- Wolf, T. J. A., Sanchez, D. M., Yang, J., Parrish, R. M., Nunes, J. P. F., Centurion, M., Coffee, R., Cryan, J. P., Gühr, M., Hegazy, K., Kirrander, A., Li, R. K., Ruddock, J., Shen, X., Vecchione, T., Weathersby, S. P., Weber, P. M., Wilkin, K., Yong, H., Zheng, Q., Wang, X. J., Minitti, M. P., & Martínez, T. J.
- Venue
- Nature Chemistry
- Published
- 2019-04-15
- Volume
- 11
- Issue
- 6
- Pages
- 504-509
- ISSN
- 1755-4330 (ISSN-L)
- 1755-4349
- OpenAlex
- W2937798275
- Cited by
- 246
- References
- 2
- FWCI
- 13.89
- Type
- journal article
- Language
- en
- Open access
- green
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- Wolf, T. J. A., Sanchez, D. M., Yang, J., Parrish, R. M., Nunes, J. P. F., Centurion, M., Coffee, R., Cryan, J. P., Gühr, M., Hegazy, K., Kirrander, A., Li, R. K., Ruddock, J., Shen, X., Vecchione, T., Weathersby, S. P., Weber, P. M., Wilkin, K., Yong, H., . . . Martínez, T. J. (2019). The photochemical ring-opening of 1,3-cyclohexadiene imaged by ultrafast electron diffraction. Nature Chemistry. https://doi.org/10.1038/s41557-019-0252-7
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