ABSTRACT
Perylene dyes have been widely used as photoreceptors in organic photovoltaics because of their outstanding photo-, thermal and chemical stability as well as their excellent photophysical properties. Herein we describe a novel generation of perylene dyes based on N-(2,6-diisopropylphenyl)-perylene-3,4-dicarboximide. The optical properties of these novel perylenes can be finely tuned via the substituents in the 1-, 6- and 9-positions of the perylene core. The facile synthesis, tunable orbital and absorption properties, and electrochemical potentials help us to design efficient perylene sensitizers for solar-cell applications.
ABSTRACT
Two new synthetic approaches to terrylenediimides, highly photostable fluorescent dyes, are described. For the first time terrylenediimide has been synthesised in a straightforward procedure that makes large quantities available. The second route includes an efficient cross-coupling reaction followed by a cyclodehydrogenation. Monofunctionalisation of the imide structure allows terrylenediimides now to be coupled with a variety of compounds, for example, by Suzuki cross-coupling, which can lead to an array of terrylenediimides with new functional groups such as hydroxy, amino, or carboxy groups needed to link up with other molecules. The functionalisation in the bay region is used to tune the properties of terrylenediimides and extend the range of applications, for example, by introducing water solubility. These tetrasubstituted terrylenediimides offer, depending on the substituents used, exciting features such as good solubility in common organic solvents, water solubility, or NIR absorption.
ABSTRACT
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.
