Ing. Pavel Jakubík from Department of Advanced Materials and Organic Synthesis has successfully defended his Ph.D. thesis on Optimization of Photochemical Helicene and Phenacene Preparation at the Department of Organic Technology, UCT Prague. The work was done under supervision of Dr. Jan Storch and it was focused on preparation of the above-mentioned polyaromatics by photocyclization in a continuous-flow mode. Helicenes and phenacenes are unique for their optical and electronic properties promising possible application in organic electronic devices such as OLED or OFET. However, the application is still rather under-developed due to low synthetic availability. The accessibility of these molecules in a multi-gram scale level can be achieved by implementation of the continuous-flow reactor. Within this work, this methodology was optimized for several helicene, phenacene and phenanthrene derivatives as model compounds. Subsequently, a series of new compounds was prepared including derivatives which are otherwise difficult to access, such as fluorinated helicenes or azaphenacenes. These derivatives were prepared in a sufficient amount allowing further investigation of their electronic properties for construction of OFETs or OLEDs by well-established research partners. Some parts of the results achieved during the thesis course have been published in prestigious international journals
- Církva, V.; Jakubík, P.; Strašák, T.; Hrbáč, J.; Sýkora, J.; Císařová, I.; Vacek, J.; Žádný, J.; Storch, J. Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings. J. Org. Chem. 2019, 84 (4), 1980–1993.
- Roth, A.; Schaub, T. A.; Meinhardt, U.; Thiel, D.; Storch, J.; Církva, V.; Jakubík, P.; Guldi, D. M.; Kivala, M. p-Doping of graphene in hybrid materials with 3,10-diazapicenium dications. Chem. Sci. 2017, 8 (5), 3494–3499.
- Jakubec, M.; Beránek, T.; Jakubík, P.; Sýkora, J.; Žádný, J.; Církva, V.; Storch, J. 2-Bromo[6]helicene as a Key Intermediate for [6]Helicene Functionalization. J. Org. Chem. 2018, 83 (7), 3607–3616.
