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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 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.