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Performance of density functional theory for calculating the electronic, static, and dynamic nonlinear optical properties of asymmetric (3E,5E)-3,5-dibenzylidene-piperidin-4-one derivatives

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Abstract

The electronic charge delocalization in organic compounds with a donor–acceptor system allows them to exhibit excellent nonlinear optical characteristics. From the perspective of conjugation, mono-carbonyl curcuminoids also have a fascinating skeleton. Interesting chemical structures of the (3E,5E)-3,5-dibenzylidene-piperidin-4-one derivatives motivate us to perform density functional theory-based studies. In investigating the derivates, geometric parameters, highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energies, and nonlinear optical (NLO) parameters calculations were performed using B3LYP/6-311++G(d,p) level of theory. Root mean square error (RMSE) calculations revealed excellent agreement between calculated and experimental parameters. The molecular stability of chalcone derivatives was investigated using molecular electrostatic potential analyses, which were also used to gain information regarding atomic charges. Calculated HOMO–LUMO energies showed that charge transfer interactions occur within the molecules. The HOMO and LUMO energies were used to compute hardness, softness, ionization potential, and electrophilicity. The \(\lambda_{max}\) values of the investigated compounds are greater than that of the reference compound. Among all other derivatives, B4 has the highest amplitude of static linear polarizability (\({\upalpha }_{tot}\)) and first total hyperpolarizability (\({\upbeta }_{tot}\)) values at 101.15 and 554.11 × 10–30 esu, respectively. Compelling NLO findings reveal that bis-chalcones-based derivatives could substantially contribute to NLO technology.

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The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Acknowledgements

LAM acknowledges postdoctoral funding from the Manajemen Talenta BRIN fellowship program 2023 No. 15/II/HK/2023. The calculations were partly performed at Mahameru High-Performance Computing, National Research and Innovation Agency (BRIN) and SymBaHCat Cluster belonging to the Symbah Foundation.

Funding

L.A.M. acknowledges funding from Manajemen Talenta BRIN fellowship program 2023 No. 15/II/HK/2023.

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Authors and Affiliations

  1. Research Center for Quantum Physics, National Research and Innovation Agency (BRIN), South Tangerang, 15314, Indonesia

    Lala Adetia Marlina, Wilin Julian Sari & Wahyu Dita Saputri

  2. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, 55281, Indonesia

    Aulia Sukma Hutama, Septiana Nur Zanah & Mokhammad Fajar Pradipta

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  1. Lala Adetia Marlina
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  2. Aulia Sukma Hutama
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  3. Septiana Nur Zanah
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  6. Wahyu Dita Saputri
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Contributions

LAM conceived the idea, led the investigation and methodology, and equally contributed to data curation, formal analysis, funding acquisition, and writing the original draft. ASH contributed equally to formal analysis, supervision, validation, and original draft writing. SNZ and MFP provided support in the investigation. WJS assisted in writing, reviewing, and editing the manuscript. WDS took the lead in supervision and equally contributed to reviewing and editing the manuscript.

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Correspondence to Aulia Sukma Hutama or Wahyu Dita Saputri.

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11082_2023_5383_MOESM1_ESM.pdf

Cartesian coordinate of optimized compounds, HOMO−LUMO map of the parent molecule, and hyperpolarizability tensor of the tested compounds. (PDF 359 kb)

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Marlina, L.A., Hutama, A.S., Zanah, S.N. et al. Performance of density functional theory for calculating the electronic, static, and dynamic nonlinear optical properties of asymmetric (3E,5E)-3,5-dibenzylidene-piperidin-4-one derivatives. Opt Quant Electron 55, 1081 (2023). https://doi.org/10.1007/s11082-023-05383-7

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