Synthesis, characterization of novel cyclohexenone derivatives and computation of their optical response

• A viable approach for the synthesis of five new cyclohexenone derivatives from Robinson annulation is described.
• Micro- and spectral analysis have been effectively operated to confirm the molecular structures of cyclohexenones.
• As-synthesized cyclohexenones exhibit intense violet fluorescence and display high hyperpolarizability values.
• The computed and experimental electronic transitions are in good agreement.

The present study reports the successful development of five new cyclohexenone derivatives (CDs) using rational design synthesis principles and quantum chemical calculations. These new CDs were synthesized by following a convenient route of Robinson annulation, and the molecular structure of these CDs were later confirmed by various analytical techniques such as 1H NMR, 13C NMR, FT-IR, UV–Vis spectroscopy and Mass spectrometry. The results from spectroscopic studies show that the as-synthesized CDs molecules apparently emit violet light at about 406–414 nm. Moreover, polarizability (α) and first static hyperpolarizability (β) were computed by density functional theory (DFT). In addition, the UV–Vis spectra, transition character and electronic structures of these CDs were computed by using the time dependent density functional theory (TD-DFT). It was interesting to note that the values of computed and experimental electronic transitions (λmax) were in good agreement. Finally, the measurements of higher non-linear optical (NLO) response of our newly synthesized CDs suggest their potential for application in photonic devices.

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