A novel achiral monomer end-capped with a phenyl-[1,3,4]oxadiazolyl group and threaded through beta-cyclodextrin was synthesized to investigate the host-guest interactions in the inclusion complex. H-1 NMR studies revealed that one or two cyclodextrin molecules were threaded onto the synthesized achiral monomer, leading to the formation of a fibrous construction of self-assembled inclusion complexes. The formation of a self-assembled inclusion complex was identified using SEM and TEM. The highly ordered alignment of self-assembled supramolecules was confirmed using polarized optical microscopy. We demonstrate an easy process for the fabrication of nano-structured self-assembled inclusion complexes in pyridine/ethanol (1 mL/10 mL) as well as the enhancement of photo-induced fluorescence via monomers end-capped with a phenyl-[1,3,4]oxadiazolyl moiety threaded with beta-cyclodextrins. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3368-3374, 2010