Facile Synthesis and Evaluation of Electron Transport and Photophysical Properties of Photoluminescent PDI Derivatives.

Abstract

Perylenediimides (PDIs) have emerged as potential materials for optoelectronic applications. In the current work, four PDI derivatives, substituted at imide nitrogen with 2,6-diisopropyl phenyl, 2-nitrophenyl, diphenylmethylene, and pentafluorophenyl groups, have been synthesized from perylene 3,4,9,10-tetracarboxylic dianhydride using a facile imidization synthesis process. PDI derivatives have been spectroscopically characterized for their structure and optical properties. Temperature-variable absorption and emission spectroscopy study confirmed the H-aggregation property. H-aggregation along with strong emission suggests the slipped π–π stacking of PDI molecules. Electrochemical analysis was performed for their redox behavior and calculation of lowest unoccupied molecular orbital and highest occupied molecular orbital energy levels. Scanning electron microscopy showed the formation of ordered structures. The PDI derivatives showed excellent electron conductivity without doping and 5–10× higher electron mobility than that of state-of-the-art fullerene acceptor phenyl-C61-butyric acid methyl ester (PC61BM). Finally, the charge generation and charge transfer phenomenon was studied by transient absorption spectroscopy (TAS). TAS showed ultrafast charge transfer from the poly(3-hexyl)thiophene (P3HT) donor polymer to PDI and formation of long-lived charge-separated states similar to fullerene derivative PC61BM/P3HT blends. Such PDI derivatives with excellent solubility and photophysical and electronic properties are potential n-type materials to be used in organic electronic devices.