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Amino-substituted pyrrole-fused perylenebis(dicarboximides) have been prepared from tri- or tetrabromoperylene prcursors by using the classical azidation conditions for the substitution of aromatic halogen, that is, NaN3, sodium ascorbate, CuI, and N, N-dimethylethane-1,2-diamine in DMSO/H2O. The pyrrole-fused dyes are highly photochemically and thermally stable, which may be useful for labelling and as building blocks for the synthesis of functional molecular materials. [ABSTRACT FROM AUTHOR]

A perylenetetracarboxdiimide derivative containing an anthraquinone unit has been synthesized by the phototriggered intramolecular cyclization of 2-anthraquinone-substituted perylenetetracarboxdiimide. The anthraquinone-substituted perylenetetracarboxdiimide dyes showed excellent electron-accepting abilities with four reversible reduction potentials. Photovoltaic devices of ITO/PEDOT:PSS/P3HT:PDIs/Ca/Al were fabricated and power conversion efficiencies of 0.16 and 0.39 were obtained for 1 and 2, respectively. [ABSTRACT FROM AUTHOR]

Abstract: A series of anthracenyl(anthraquinonyl)-substituted difluoroboron dipyrromethene dyes were synthesized through a Suzuki cross-coupling reaction. The crystal structure combined with geometric optimization reveals a moderate dihedral angle between the anthracenyl(anthraquinonyl) plane and the connected pyrrolyl plane. Photophysical characterization shows that the introduction of anthracenyl(anthraquinonyl) moiety to the BODIPY core effectively tunes the emission properties of BODIPY while retaining the separate absorption properties of BODIPY and anthracene(anthraquinone). High fluorescent quantum yields of up to 0.70 and a large Stokes shift (ca. 1707 cm−1) were noted. Electrochemical characterization suggests that the anthracenyl(anthraquinonyl) linkage and BODIPY unit lead to rich and tunable potentials. TD-DFT calculation proved a moderate intramolecular charge-transfer process between the BODIPY core and anthracenyl(anthraquinonyl) moiety. [Copyright &y& Elsevier]