Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

Scholarly Works

• Cho, S.; Usuba, J.; Chakraborty, S.; Li, X.; Han, G. G. Solid-state photon energy storage via reversible [2+2] cycloaddition of donor-acceptor styrylpyrylium system. Chem 2023, 9, 3159–3171. doi:10.1016/j.chempr.2023.06.007
• Ljubić, A.; Šalić, A.; Škorić, I. Synthesis of Hydroxylated Stilbenes in a Batch and Flow Reactor: An Overview. ChemistrySelect 2023, 8. doi:10.1002/slct.202303375
• Li, X.; Cho, S.; Wan, J.; Han, G. G. Photoswitches and photochemical reactions for optically controlled phase transition and energy storage. Chem 2023, 9, 2378–2389. doi:10.1016/j.chempr.2023.05.029
• Storch, J.; Žádný, J.; Církva, V.; Jakubec, M.; Hrbáč, J.; Vacek, J. doi:10.1002/9783527829415.ch1
• Nishida, J.; Matsuno, K.; Kawase, T. Synthesis, Photophysical and Electrochemical Study of 1,3,6,8‐Tetraarylsubstituted X‐Shaped Phenanthrene Derivatives. Asian Journal of Organic Chemistry 2022, 11. doi:10.1002/ajoc.202100789
• Yadykov, A. V.; Lvov, A. G.; Krayushkin, M. M.; Zakharov, A. V.; Shirinian, V. Z. Photocyclization of Diarylethenes: The Effect of Electron and Proton Acceptors as Additives. The Journal of organic chemistry 2021, 86, 10023–10031. doi:10.1021/acs.joc.1c00723
• Seylar, J.; Stasiouk, D.; Simone, D. L.; Varshney, V.; Heckler, J. E.; McKenzie, R. Breaking the bottleneck: stilbene as a model compound for optimizing 6π e− photocyclization efficiency. RSC advances 2021, 11, 6504–6508. doi:10.1039/d0ra10619d
• Kos, M.; Žádný, J.; Storch, J.; Církva, V.; Cuřínová, P.; Sýkora, J.; Císařová, I.; Kuriakose, F.; Alabugin, I. V. Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs. International journal of molecular sciences 2020, 21, 5868. doi:10.3390/ijms21165868
• Mizuno, K.; Kakiuchi, K. Chapter 4:Perspectives on the Use of Flow Systems to Carry Out Organic Photochemical Reactions. Flow Chemistry; The Royal Society of Chemistry, 2019; pp 129–152. doi:10.1039/9781788016094-00129
• Murase, T. Synthesis of the Longest Carbohelicene by Multiple Oxidative Photocyclizations of Arylene–Vinylene Oligomers. Designed Molecular Space in Material Science and Catalysis; Springer Singapore, 2018; pp 69–90. doi:10.1007/978-981-13-1256-4_4
• Hafedh, N.; Aloui, F.; Raouafi, S.; Dorcet, V.; Hassine, B. B. New [4]helicene derivatives: Synthesis, characterization and photophysical properties. Journal of Molecular Liquids 2018, 262, 310–316. doi:10.1016/j.molliq.2018.04.083
• Ravat; Hinkelmann, R.; Steinebrunner, D.; Prescimone, A.; Bodoky, I.; Juríček, M. Configurational Stability of [5]Helicenes. Organic letters 2017, 19, 3707–3710. doi:10.1021/acs.orglett.7b01461
• Murase, T.; Suto, T.; Suzuki, H. Azahelicenes from the Oxidative Photocyclization of Boron Hydroxamate Complexes. Chemistry, an Asian journal 2017, 12, 726–729. doi:10.1002/asia.201700096
• Chen, M.; Zhao, X.; Yang, C.; Wang, Y.; Xia, W. Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes. RSC Advances 2017, 7, 12022–12026. doi:10.1039/c7ra00193b
• Mizuno, K.; Nishiyama, Y.; Ogaki, T.; Terao, K.; Ikeda, H.; Kakiuchi, K. Utilization of microflow reactors to carry out synthetically useful organic photochemical reactions. Journal of Photochemistry and Photobiology C: Photochemistry Reviews 2016, 29, 107–147. doi:10.1016/j.jphotochemrev.2016.10.002
• Chen, C.-F.; Shen, Y. Oxidative Photocyclization. Helicene Chemistry; Springer Berlin Heidelberg, 2016; pp 43–70. doi:10.1007/978-3-662-53168-6_3
• Millet, A.; Lefebvre, Q.; Rueping, M. Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins. Chemistry (Weinheim an der Bergstrasse, Germany) 2016, 22, 13464–13468. doi:10.1002/chem.201602257
• Yamamoto, A.; Matsui, Y.; Asada, T.; Kumeda, M.; Takagi, K.; Suenaga, Y.; Nagae, K.; Ohta, E.; Sato, H.; Koseki, S.; Naito, H.; Ikeda, H. Amorphous Solid Simulation and Trial Fabrication of the Organic Field-Effect Transistor of Tetrathienonaphthalenes Prepared by Using Microflow Photochemical Reactions: A Theoretical Calculation-Inspired Investigation. The Journal of organic chemistry 2016, 81, 3168–3176. doi:10.1021/acs.joc.6b00117
• Cambié, D.; Bottecchia, C.; Straathof, N. J. W.; Hessel, V.; Noël, T. Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment. Chemical reviews 2016, 116, 10276–10341. doi:10.1021/acs.chemrev.5b00707
• Lefebvre, Q.; Hoffmann, N.; Rueping, M. Photoorganocatalysed and visible light photoredox catalysed trifluoromethylation of olefins and (hetero)aromatics in batch and continuous flow. Chemical communications (Cambridge, England) 2016, 52, 2493–2496. doi:10.1039/c5cc09881e

Explore citations to this article at