Dendronized Perylenetetracarboxdiimides with Peripheral Triphenylamines for Intramolecular Energy and Electron Transfer

Novel perylene‐3,4,9,10‐tetracarboxdiimides (PDI) dyes functionalized with polyphenylene dendrimers attached at the bay region are reported. Derivatives of PDI bearing polyphenylene dendrimers up to the second generation, substituted with an increasing number of triphenylamine (TPA) moieties at the...

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Bibliographic Details
Published in:Chemistry : a European journal 2004-01, Vol.10 (2), p.528-537
Main Authors: Qu, Jianqiang, Pschirer, Neil G., Liu, Daojun, Stefan, Alina, De Schryver, Frans C., Müllen, Klaus
Format: Article
Language:English
Subjects:
cycloaddition
dendrimers
electron transfer
energy transfer
perylenes
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Summary:Novel perylene‐3,4,9,10‐tetracarboxdiimides (PDI) dyes functionalized with polyphenylene dendrimers attached at the bay region are reported. Derivatives of PDI bearing polyphenylene dendrimers up to the second generation, substituted with an increasing number of triphenylamine (TPA) moieties at the periphery, as well as a related nondendronized model compound were prepared. Intramolecular energy transfer was demonstrated by the observation of PDI emission on excitation of the triphenylamines, and electron transfer was detected by comparing photoluminescence quenching in solvents of different polarity. Donor–spacer–acceptor systems were built up by using shape‐persistent polyphenylene dendrimers as bridges between a perylenetetracarboxdiimide core and peripheral triphenylamino groups. Intramolecular energy and electron transfer were observed between the perylenetetracarboxdiimide core and the triphenylamino groups via the polyphenylene dendron, which can be controlled by means of the generation of the dendrimers or by varying the polarity of the solvent. The picture shows the second‐generation dendrimer.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200304994