Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 19, Pages 5289-5299Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201003232
Keywords
amphiphiles; click chemistry; coronenes; dendrimers; perylenes
Categories
Funding
- Deutsche Forschungsgemeinschaft (DFG)
- Cluster of Excellence Engineering of Advanced Materials (EAM)
- European Research Council (ERC)
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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.
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