Herein, we submitted to the original synthesis, characterization, energy transfer mechanism of the Bodipy-bearing pillar[5]arene Bodipy and its reactants by employing of infrared, 1H, 11B, 13C, 19F-NMRs, UV–vis, fluorescence spectroscopy, melting point apparatus, CHN elemental analysis and mass spectroscopy. Preliminary UV–vis, fluorescence and excitation measurements were carried out in CH2Cl2 and the results revealed an effective fluorescence resonance energy transfer (FRET) system based on the interaction of pillar[5]arene and Bodipy derivative. εmax of target molecule reached to a maximum value and it was found as 955 000 M−1 cm−1. This fluorescent macromolecule worked well for mimicking a light harvesting system with an energy transfer efficiency up to 92%.