Schmidt C, Lang N, Jux N, Hirsch A (2011)
Publication Type: Journal article, Original article
Publication year: 2011
Original Authors: Schmidt C.D., Lang N., Jux N., Hirsch A.
Publisher: Wiley-VCH Verlag
Book Volume: 17
Pages Range: 5289-5299
Journal Issue: 19
Click reactions at the bay-position of perylenes and a new route to benzo[ghi]perylenes and coronenes are presented. Irradiation with light leads to an electrocyclic reaction of the newly formed triazole ring(s) with the neighbouring bay-positions of the perylene core and after oxidation by air, the benzo[ghi]perylenes and coronenes are obtained. By using Newkome dendrimers as substituents for perylene diimides (PDIs), water solubility can be achieved after removal of the tert-butyl protecting groups. The aggregation and optical properties of the bay-functionalised PDIs, benzo[ghi]perylenes and coronenes are investigated by absorption and fluorescence spectroscopy. Given the green light: Click reactions at the bay-positions of perylene diimides were carried out for the first time. The newly formed triazole units undergo electrocyclisation reactions with the neighbouring perylene bay-position to form benzoperylenes or coronenes (see scheme). The reactions occur in solution in 55-87%yield by irradiation with light, providing a simple, new and environmentally friendly route to coronenes and benzoperylenes. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
APA:
Schmidt, C., Lang, N., Jux, N., & Hirsch, A. (2011). A facile route to water-soluble coronenes and benzo[ghi]perylenes. Chemistry - A European Journal, 17(19), 5289-5299. https://doi.org/10.1002/chem.201003232
MLA:
Schmidt, Cordula, et al. "A facile route to water-soluble coronenes and benzo[ghi]perylenes." Chemistry - A European Journal 17.19 (2011): 5289-5299.
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