Photophysical property, electronic structure and solid-state packing of O-heterocyclic annulated perylene diimide

Abstract

PurposeSelf-organization has been regarded as a tool for the synthesis of well-defined organic nanostructures. Heterocyclic annulated perylene diimides are the subjects of considerable current research studies. The purpose of this study is to reveal the photophysical property, electronic structure and solid-state packing of O-heterocyclic annulated perylene diimide.Design/methodology/approachAsymmetrically five-membered O-heterocyclic annulated perylene diimide (OAPDI) was synthesized. Structure and purity of OAPDI were confirmed by 1H NMR, 13C NMR, IR and mass spectral techniques. Photophysical properties of OAPDI were studied using UV–vis absorption and fluorescence in both solution (CHCl3) and solid state. Scanning electron microscopic and atomic force microscopy were used to characterize the surface morphology of OAPDI. Conducting properties of the OAPDI were evaluated by current–voltage measurements. The compounds geometries were also optimized at 6-31G* using density functional theory.FindingsThe UV–vis absorption and fluorescence spectra of OAPDI in solution are blue-shifted in comparison with that of unsubstituted perylene bisimide. Solid-state UV–vis measurements of OAPDI indicate that it is capable of forming highly ordered structure. The non-covalent interactions, electrostatic attraction and p-p stacking moieties of OAPDI synergistically guide assembly and domain growth while maintaining the interpenetrating network of nanofibers in the solid film. The OAPDI gave higher current at −2.0 V (0.68 µA) and 4.0 V (1.0 µA).Originality/valueThis study will be helpful for exploring feasible routes to acquire soluble perylene diimides and well-defined organic nanostructures. Furthermore, such molecular tailoring approach would be helpful for designing and synthesizing novel organic semiconductive materials with excellent charge-transporting and light-emitting capabilities.