We present a detailed photophysical properties of a synthesized charge transfer (CT) molecule (2E, 4E)-ethyl 2-cyano-5-(4-(dimethylamino) phenyl) penta-2, 4-dienoate (ECDPPD) in bulk medium and its spectral modulation inside β-Cyclodextrin cavity. Enhancement of acceptor strength of 4-(dimethylamino) cinnamaldehyde by replacing the moderate acceptor in the form of a Formyl group by two acceptors known to display greater electron withdrawing ability along with extra conjugation which may be responsible for higher dipole moment both in ground as well as in excited state. The observed excited CT process and its solvent polarity dependent emissive properties is due to simply increasing the ‘end-to-end’ length between donor and acceptor along with introduction of two different acceptors in the same site. Low fluorescence quantum yield and shorter fluorescence lifetime is due to the operation of active non-radiative channels through flexible bonds supported by viscosity and temperature dependent spectral measurement. The molecule ECDPPD easily interacts with β-CD with the formation of inclusion complex with a definite stoichiometry where the photophysics are modulated and hence can be used as fluorescence microenvironment reporter for example to evaluate the polarity as well as the micro viscosity of various regions of protein and other bimolecular systems. © 2018 Elsevier B.V.