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Keywords:

  • amphiphiles;
  • click chemistry;
  • coronenes;
  • dendrimers;
  • perylenes

Abstract

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.