Preparation of new helicene derivatives
The synthetic approach leading to helicenes is based on a patented photooxidative cyclization of stilbene precursors. By transferring the synthesis to a flow system, we are capable of preparing helicenes on a multigram scale, which is sufficient not only for studying their properties and applications but also for further chemical transformations. Helicenes usually undergo reactions that are typical for simpler aromatics; their reactivity, however, is non-trivial, and thorough optimization is often required even for otherwise simple reactions. Nevertheless, it is often possible to introduce reactive functionalities either before the cyclization or in the later stages. This leads to the preparation of versatile materials with enormous application potential. Some helicene derivatives exhibit intrinsic photochemistry, which can be easily exploited for otherwise forbidden transformations.
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- 9-Bromo[7]Helicene Reactivity. Tetrahedron 69(30), 6213-6218, 2013. DOI
- Helicene-Based Imidazolium Salt and Its Application in Organic Molecular Electronics. Chem. Eur. J. 21(6), 2343-2347, 2015. DOI
- Cation-π Interaction of Ag+ + [6]helicene. Chem. Phys. Lett. 633, 105-108, 2015. DOI
- Cation-π Interaction of Tl+ + [6]helicene. J. Mol. Struct. 1100, 150-153, 2015. DOI
- Chiral Resolution of Helicenes. J. Chromatogr. A 1476, 130-134, 2016. DOI
- Internal Dynamics in Helical Molecules. Phys. Chem. Chem. Phys. 19(4), 2900-2907, 2017. DOI
- 2-Bromo[6]Helicene Reactivity. J. Org. Chem. 83(7), 3607–3616, 2018. DOI
- [6]Helicenes Fluorinated at Terminal Rings. J. Org. Chem. 84(4), 1980-1993, 2019. DOI
- Cytotoxicity of Hexahelicene. Toxicology in Vitro 57, 105-109, 2019. DOI
- Photochemical Functionalization of Helicenes. Chem. Eur. J. 26(2), 543-547, 2020. DOI
- Synthesis of a Helical Phosphine. ACS Omega 5(1), 882-892, 2020. DOI
- Photochemical Oxidation of Helical Aromatic Amines. Org. Lett. 22(10), 3905-3910, 2020. DOI
- Recent Advances in Functionalizations of Helicene Backbone. J. Org. Chem. 85(11), 13415-13428, 2020. DOI
- Oxidative Photocyclization of Aromatic Schiff Bases. Inter. J. Mol. Sci. 21(16), 5868, 2020. DOI
- Enantioenriched Ruthenium Complexes of Azahelicenes. Inorg. Chem. 60(16), 11838-11851, 2021. DOI
- Flavin-Helicene Amphiphilic Hybrids. ChemPlusChem 86, 982, 2021. DOI
- Photochemical Approach to Helicenes. in book Helicenes: Synthesis, Properties, Applications 1-52, 2022. DOI
- Synthesis of Aza[n]helicenes (n = 4-7). J. Org. Chem. 87(11), 7150–7166, 2022. DOI
- Push-pull Phosphine Oxide-based Helicenes. Dyes Pig. 210, 111039, 2023. DOI
- Hexahelicene DNA-binding. Int. J. Biol. Macromol. 250, 125905, 2023. DOI
- Resolution of 9,10-diketo[7]helicene and D−A−D Push−Pull Systems. J. Org. Chem. 89(11), 7495-7502, 2024. DOI
- Biomolecular Interactions of Helicenes. Biotechnology Advances 79(1 March), 108513, 2025. DOI