Abstract
Terrylene diimide derivatives are pigments for dyes and optoelectric devices. A terrylene diimide derivative N,N'-di(1-undecyldodecyl)terrylene-3,4:11,12-tetracarboxdiimide (DUO-TDI) decorated with long branched alkyl chains on both imide nitrogen atoms was designed and synthesized. The supramolecular assembly behaviors of DUO-TDI in solution and at the liquid-solid interface were both investigated. The assembled nanostructures and photophysical properties of TDI in solution were explored by varying solvent polarity with spectral methods (UV-Vis, FL and FT-IR) and morphological characterization (AFM). Depending on the solution polarities, fibers, disk structures and wires could be observed and they showed diverse photophysical properties. In addition, the interfacial assembly of DUO-TDI was further investigated at the liquid-Highly Oriented Pyrolytic Graphite (HOPG) interface probed by scanning tunneling microscope (STM). Long range ordered monolayers composed of lamellar structures were obtained. The assembly mechanisms were studied for DUO-TDI both in solution and at the interface. Our investigation provides alternative strategy for designing and manipulation of supramolecular nanostructures and corresponding properties of TDI based materials.
Highlights
Rylene diimide dyes derivatives are famous for their outstanding photophysical and photochemical stability and their high fluorescence quantum yield (Zhao et al, 2016; Feng et al, 2017; Frankaer et al, 2019)
As indicated in the Scheme 1, a large aromatic core exists between two branched alkyl chains
We reported the self-assembly of this n-type semiconductor at the liquid-Highly Oriented Pyrolytic Graphite (HOPG) interface
Summary
Rylene diimide dyes derivatives are famous for their outstanding photophysical and photochemical stability and their high fluorescence quantum yield (Zhao et al, 2016; Feng et al, 2017; Frankaer et al, 2019). The concentration-dependent UVVis absorption spectra of DUO-TDI in THF solutions were studied (Figure 1A). The emission of DUO-TDI was completely quenched in the cast film, suggesting the main formation of H-type molecular packing in accordance with the results from UV-vis data (Jung et al, 2006).
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