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A Facile Route to Water‐Soluble Coronenes and Benzo[ ghi ]perylenes
Author(s) -
Schmidt Cordula D.,
Lang Nina,
Jux Norbert,
Hirsch Andreas
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003232
Subject(s) - water soluble , chemistry , combinatorial chemistry , organic chemistry
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.