Substitution of Aromatics by Amines at Room Temperature with Negative Energy of Activation: Amino peri-Arylenes as Metal-Free Components for Dye-Sensitized Solar Cells

Substitution reactions of the chemically and photochemically unusually stable perylenetetracarboxylic bisimides proceed with neat amines even below room temperature where negative effective energies of activation were found. Analogous reactions proceed with naphthalenecarboximides as the lower homol...

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Veröffentlicht in:Journal of organic chemistry 2013-10, Vol.78 (19), p.9883-9891
Hauptverfasser: Langhals, Heinz, Christian, Sandra, Hofer, Alexander
Format: Artikel
Sprache:eng
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Zusammenfassung:Substitution reactions of the chemically and photochemically unusually stable perylenetetracarboxylic bisimides proceed with neat amines even below room temperature where negative effective energies of activation were found. Analogous reactions proceed with naphthalenecarboximides as the lower homologues and terrylene and quaterrylene carboximides as the higher homologues. Bathochromically absorbing dyes with a novel pattern of substitution were obtained suitable as efficient metal-free light-absorbers for dye-sensitized solar cells.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401597u