Electron Accepting Perylene Dyes with Versatile Imide Substituents: Synthesis and Characterization

Perylene bisimides (PBIs) have received significant attention due to their exceptional photophysical and optical properties. Derivatives of PBIs show high fluorescence quantum yields, high electron affinities and large band-gaps‚ that make them excellent candidates for numerous optoelectronic devices such as light-emitting diodes, photovoltaics, optical switching, and electroluminescent devices. PBIs are considered as n-type semiconductors in which the main charge carriers are in their conduction band. On the other hand, most organic conducting substances are p-type semiconductors. In the current work, the synthesis of a new perylene bisimide N‚N′-Bis(1-methyl-2-cyanoethene)-3,4,9,10-perylenebis(dicarboxiimide) (EAPDI) was carried out. 1-methyl-2-cyanoethene substituent is specifically chosen so that the imide regions of perylene core offer better solubility and impressive optical properties of the perylene bisimide. The synthesized bisimide was approved by FT-IR and its photo-physical properties were studied by UV–vis and emission techniques. EAPDI has high molar absorptivity as well as high fluorescence quantum yields (Φf = 0.72). The absorption and emission spectra of EAPDI are mirrored images in DMF, CHCl3, MeOH with smaller Stoke shifts. Keywords: Perylene bisimide, 1-methyl-2-cyanoethene, absorbance, fluorescence.