New semi-conducting rotaxane based on β-cyclodextrin and anthracene moieties

A new rotaxane (BPAAn/β-CD), consisting of an anthracene-based semi-conducting material (BPAAn) encapsulated into β-cyclodextrin (β-CD), has been synthesized via the Williamson reaction in solvent-free conditions. The supramolecular structure of the compound was confirmed by NMR and FT-IR spectroscopies. The optical and morphological properties of this organic material were investigated by UV–visible absorption, photoluminescence spectroscopy and atomic force microscopy. BPAAn/β-CD film has an optical gap of 2.9 eV and exhibits green photoluminescence. An optical gap of 2.9 eV was estimated from the absorption edge of the rotaxane thin film. The BPAAn/β-CD exhibits a blue photoluminescence in dilute solution; whereas, a green emission was observed in the solid state, due to the π–π interaction in the anthracene moieties. The rotaxane shows a significantly enhanced PL quantum yield and improved film quality in comparison with the free BPAAn. The HOMO and LUMO levels were estimated using cyclic voltammetry analysis, and show enhanced electron affinity of the BPAAn in its complexed form. A single-layer device with the configuration [ITO/rotaxane/Aluminum] has been elaborated and showed low turn-on voltage of 5 V.