epsilon-Caprolactone (CL) was subjected to ring opening polymerization (ROP) under inert (nitrogen) atmosphere at 413 K for 1 h in the presence of stannous octoate (SO) as a catalyst and Eosin Y, a xanthenes type dye as a novel chemical initiator. The ROP was carried out at two different experimental conditions, namely at various concentrations of initiator and monomer, to get more scientific information from the resultant product. Thus, obtained Eosin Y conjugated poly(epsilon-caprolactone) (PCL) was characterized by different analytical tools like FTIR spectroscopy, NMR spectroscopy, gel permeation chromatography (GPC), UV-Visible spectroscopy, photoluminescence (PL) spectroscopy, X-ray photoelectron spectroscopy (XPS), and differential scanning calorimetry (DSC). Finally, the morphology of the Eosin Y conjugated PCL was studied by scanning electron microscopy (SEM). The binding constant (K) was determined from both UV-Visible spectroscopy and PL spectroscopy, and the static quenching mechanism was proposed. The number of binding site (n) was also determined from PL spectroscopy and the results were compared with the FTIR-RI method.