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Hexabenzocoronene functionalized with antiaromatic S- and Se-core-modified porphyrins (isophlorins): comparison with the dyad with regular porphyrin

  • Aleksey E. Kuznetsov EMAIL logo
Published/Copyright: January 21, 2022
Pure and Applied Chemistry
From the journal Pure and Applied Chemistry Volume 94 Issue 7

Abstract

The important and perspective molecular building blocks composed of hexaphenylbenzenes (HPBs) or their oxidized derivatives, hexa-peri-hexabenzocoronenes (HBCs), and metalloporphyrins have recently received significant attention of the researchers. In this study, motivated by recent findings, we have addressed the modifications of structures and properties of HBC-porphyrin compounds by using instead of aromatic porphyrins antiaromatic 20π isophlorin derivatives of thiophene or selenophene. We have reported the first comparative computational investigation of the following systems: (i) HBC with one non-metallated aromatic porphyrin, P(N4H2), unit, HBC-P(N4H2), (ii) HBC with one S-core-modified antiaromatic porphyrin (S-isophlorin), PS4, unit, HBC-PS4, and (iii) HBC with one Se-core-modified antiaromatic porphyrin (Se-isophlorin), PSe4, unit, HBC-PSe4. The study has been done employing the B3LYP/6-31G* approach (in the gas phase and in the implicit solvents, benzene and dichloromethane), and comparison with the B3LYP/6-31G** and B3LYP/6-311G* approaches was performed, where relevant. The effects of the core-modified antiaromatic isophlorins on the structures, electronic, and other properties, potentially including reactivity, of the whole building block HBC-isophlorin have been shown to be quite pronounced and to be noticeably stronger than the effects of the original aromatic non-metallated porphyrin. Thus, we have demonstrated theoretically that the complete porphyrin core-modification with other elements, this time with S and Se leading to the formation of the antiaromatic isophlorins, should be considered as a promising way for modifying and tuning structures, electronic properties and reactivity of the hexabenzocoronene-porphyrin(s) building blocks.

Keywords: Chemistry and its applications; density functional theory approach; electronic properties; hexabenzocoronene; molecular electrostatic potential maps; molecular orbitals; NBO analysis; novel molecular building blocks; S- and Se-isophlorins; structural distortions; VCCA-2021

Article note:

A collection of invited papers based on presentations at the Virtual Conference on Chemistry and its Applications (VCCA-2021) held on-line, 9–13 August 2021.

Corresponding author: Aleksey E. Kuznetsov, Department of Chemistry, Universidad Técnica Federico Santa María, Santiago, Chile, e-mail:

Acknowledgments

The computational resources of the supercomputer facilities at Instituto Tecnologica de Aeronautica (ITA) are highly appreciated. Also, this research was supported by the high-performance computing system of PIDi-UTEM (SCC-PIDi-UTEM FONDEQUIP-EQM180180).

  1. Research funding: The author deeply acknowledges the financial support of the Universidad Tecnica Federica Santa Maria (USM), Santiago, Chile

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/pac-2021-1105).

Published Online: 2022-01-21
Published in Print: 2022-07-26

© 2022 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Editorial
  4. The virtual conference on chemistry and its applications, VCCA-2021, 9–13 August 2021
  5. Conference papers
  6. Hexabenzocoronene functionalized with antiaromatic S- and Se-core-modified porphyrins (isophlorins): comparison with the dyad with regular porphyrin
  7. Bonding analysis of the C2 precursor Me3E–C2–I(Ph)FBF3 (E = C, Si, Ge)
  8. Supporting the fight against the proliferation of chemical weapons through cheminformatics
  9. Disinfecting activity of some diphenyltin(IV) benzoate derivative compounds
  10. HCV genotype-specific drug discovery through structure-based virtual screening
  11. ExcelAutomat 1.4: generation of supporting information
  12. Use of Circular Dichroism in the characterization of the fusion protein SARS-CoV-2 S protein (RBD)-hFc
  13. Experimental determination of activation rate constant and equilibrium constant for bromo substituted succinimide initiators for an atom transfer radical polymerization process
  14. Degradation of o-, m-, p-cresol isomers using ozone in the presence of V2O5-supported Mn, Fe, and Ni catalysts
  15. The beginnings of chemistry: from ancient times until 1661
  16. Chemical substitution in processes for inherently safer design: pros and cons
  17. Experimental and theoretical study of the dye-sensitized solar cells using Hibiscus sabdariffa plant pigment coupled with polyaniline/graphite counter electrode
https://doi.org/10.1515/pac-2021-1105
Keywords for this article
Chemistry and its applications; density functional theory approach; electronic properties; hexabenzocoronene; molecular electrostatic potential maps; molecular orbitals; NBO analysis; novel molecular building blocks; S- and Se-isophlorins; structural distortions; VCCA-2021

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Editorial
  4. The virtual conference on chemistry and its applications, VCCA-2021, 9–13 August 2021
  5. Conference papers
  6. Hexabenzocoronene functionalized with antiaromatic S- and Se-core-modified porphyrins (isophlorins): comparison with the dyad with regular porphyrin
  7. Bonding analysis of the C2 precursor Me3E–C2–I(Ph)FBF3 (E = C, Si, Ge)
  8. Supporting the fight against the proliferation of chemical weapons through cheminformatics
  9. Disinfecting activity of some diphenyltin(IV) benzoate derivative compounds
  10. HCV genotype-specific drug discovery through structure-based virtual screening
  11. ExcelAutomat 1.4: generation of supporting information
  12. Use of Circular Dichroism in the characterization of the fusion protein SARS-CoV-2 S protein (RBD)-hFc
  13. Experimental determination of activation rate constant and equilibrium constant for bromo substituted succinimide initiators for an atom transfer radical polymerization process
  14. Degradation of o-, m-, p-cresol isomers using ozone in the presence of V2O5-supported Mn, Fe, and Ni catalysts
  15. The beginnings of chemistry: from ancient times until 1661
  16. Chemical substitution in processes for inherently safer design: pros and cons
  17. Experimental and theoretical study of the dye-sensitized solar cells using Hibiscus sabdariffa plant pigment coupled with polyaniline/graphite counter electrode
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