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In this study some affinity and dielectric properties of molecularly imprinted (MIP) conducting polymer—polypyrrole (Ppy) based thin films were evaluated. Films of polypyrrole molecularly imprinted with theophylline (MIP–Ppy) and non-imprinted polypyrrole (NIP–Ppy) were formed on boron doped silicon (Si) substrates in order to evaluate the efficiency of Ppy to bind theophylline. The substrates were modified with boron-doped oxygen terminated nanocrystalline diamond (B:NCD:O) The dielectric properties of B:NCD:O/Ppy-based multi-layered structures were analyzed using spectroscopic ellipsometry and spectrophotometric techniques. Electrochemical impedance spectroscopy was applied for the investigation of kinetics of theophylline interaction with MIP–Ppy and NIP–Ppy. The sensitivity of molecularly imprinted and non-imprinted polymer films was analyzed by injection of different theophylline concentrations …