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Theoretical assessment of calix[4]arene-N-β-ketoimine (n=1–4) derivatives: Conformational studies, optoelectronic, and sensing of Cu2+cation

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Abstract

Herein, we have investigated the key functions of the calix[4]arene, abbreviated as CX [1], and designed its several derivatives by substitution of the functional groups. Molecular geometry provides an intuitive understanding of the effect of functional groups on various physical properties. The addition of the N-β-ketoimine (n = 1–4) ligands has a direct effect on the stretching vibration of the H-bonding interaction. The results showed that all molecules possess absorption bands at 190 nm and in the range between 200 and 300 nm assigned to π–π* and n-π* transitions. HOMO–LUMO energy gap of the CX[4]-N-β-ketoimine, one with chemical hardness of 1.62 eV, has been found to be 3.24 eV calculated at B3LYP/6–31 + G(d) level of theory. This finding explains the good kinetic stability of this compound. The large values of electrophilicity make the current molecules as a good electrophilic species. The atom in molecule (AIM) and the reduced density gradient (RDG) analyses showed the type and the strength of the interactions taking place between Cu2+ and the β-ketoimine ligands.

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AFM image of a calix[4]arene-2β-ketoimine film deposition, absorption spectra of the calix[4]arene-2β-ketoimine…Cu2+complex and Frontier Molecular Orbital analysis, and global reactivity parameters of the studied compounds are given in Figs. S1, S2, S3, and Table S1.

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Acknowledgments

We thank to, Dr. Arzu Karayel and Dr. Sevil Özkınalı for the theoretical calculations of the calix[4]arene- N-β-ketoimine…Cu2+complexes. The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, high performance, and Grid Computing Center (TRUBA resources).

Funding

The authors acknowledge financial support from the Tunisian’s Ministry of high education and scientific research.

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Authors and Affiliations

  1. Laboratory of Advanced Materials and Interfaces (LIMA), Faculty of Science of Monastir, Avenue of Environnment, University of Monastir, 5000, Monastir, Tunisia

    B. Gassoumi & R. Ben. Chaabane

  2. Institute of Light and Matter, UMR5306 University of Lyon1-CNRS, University of Lyon, 69622, Villeurbanne Cedex, France

    B. Gassoumi

  3. Department of Physics, Faculty of Arts and Sciences of AlMikhwah, Al-BAHA University, Al Baha, Kingdom of Saudi Arabia

    F. E. Ben Mohamed & N. Khedmi

  4. Department of Physics, Faculty of Arts and Sciences, Hitit University, Çorum, Turkey

    A. Karayel

  5. NANOMISENE Lab, LR16CRMN01, Centre for Research on Microelectronics and Nanotechnology CRMN of Technopark of Sousse, B.P. 334, Sahloul, 4034, Sousse, Tunisia

    M. Echabaane

  6. Quantum and Statistical Physics Laboratory, Faculty of Science, University of Monastir, 5079, Monastir, Tunisia

    H. Ghalla

  7. Department of Chemistry, Faculty of Arts and Sciences, Hitit University, Çorum, Turkey

    S. Özkınalı

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  1. B. Gassoumi
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Contributions

B. Gassoumi: wrote the paper, conceived and designed the analysis.

F.E. Ben Mohamed, N. Khedmi, M. Echabaane: performed a part of calculation and interpret some results.

A. Karayel, S. Özkınalı: analyzed and interpreted the data;

H. Ghalla: performed the AIM analysis.

R. Ben. Chaabane: supervisor of the paper.

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Correspondence to B. Gassoumi or R. Ben. Chaabane.

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Gassoumi, B., Mohamed, F.E.B., Khedmi, N. et al. Theoretical assessment of calix[4]arene-N-β-ketoimine (n=1–4) derivatives: Conformational studies, optoelectronic, and sensing of Cu2+cation. J Mol Model 27, 16 (2021). https://doi.org/10.1007/s00894-020-04622-y

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