Charge transfer (CT) complexes of p-benzoquinone derivatives with Indolyldiene aniline derivatives have been prepared and investigated by Elemental analysis, IR,1H-NMR and electronic absorption spectroscopy. The spectral changes revealed that acidic acceptors form complexes with π - π* electronic interaction and proton transfer while non-acidic acceptors yield complexes having π - π transition only. The formation of 1:2 (D:A) complexes is also ascertained. The ionization potential and electron affinity are determined from the electronic absorption spectra for both the donors and acceptors respectivily.