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Synthesis, characterization and structure–activity relationship of non-linear optical response of chalcone derivatives with in silico insights

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Fifteen chalcone derivatives having D–A–D, D–A–A and A–A–D architectures have been synthesized by Claisen–Schmidt condensation reaction and characterized by UV–Vis, IR, 1H-NMR, 13C-NMR and Mass spectrometry. In order to unambiguously establish the structure–activity relationship for the non-linear optical activity of these compounds, for the first time to our knowledge, we use the femtosecond degenerate four wave mixing (DFWM) technique to quantify and compare the third-order non-linear optical (NLO) activity of all the 15 compounds, under identical conditions. The second harmonics generation (SHG) efficiencies for all the compounds have also been evaluated using the Kurtz-Perry powder method. Among the compounds that we have synthesized here, the ones with A–A–D architecture show the highest NLO activity. Our results show that the NLO activity of a compound with A–A–D architecture can be further enhanced by incorporating a substituent with strong electron withdrawing ability on ring A and strong electron donating substituent on ring B. The results of the in silico studies that we have carried out correlate well with our experimental findings. The compounds (E)-3-(4-(dimethylamino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-N(CH3)2–4′-NO2) and (E)-3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-MeO-4′-NO2) show the highest NLO activity among the compounds we have reported here.

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The authors dedicate this work to Bhagwan Sri Sathya Sai Baba, the Founder Chancellor of SSSIHL, for being a constant source of inspiration. The authors thank Central Research Instruments Facility (CRIF), SSSIHL for providing all the facilities necessary for carrying out this work.

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Correspondence to Nageswara Rao Golakoti.

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Rai, P., Chettri, P., Kar, S. et al. Synthesis, characterization and structure–activity relationship of non-linear optical response of chalcone derivatives with in silico insights. Chem. Pap. 75, 2603–2615 (2021).

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