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Article

Post Synthetic Modification of Planar Antiaromatic Hexaphyrin (1.0.1.0.1.0) by Regio-Selective, Sequential SNAr

1
Department of Chemistry, Kangwon National University, Chuncheon 24341, Korea
2
Kangwon Radiation Convergence Research Support Center, Kangwon National University, Chuncheon 24341, Korea
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: M. Graça P. M. S. Neves
Molecules 2021, 26(4), 1025; https://doi.org/10.3390/molecules26041025
Received: 18 January 2021 / Revised: 7 February 2021 / Accepted: 9 February 2021 / Published: 15 February 2021
(This article belongs to the Special Issue Supramolecular Anion Binding and Molecular Recognition)
In spite of unique structural, spectroscopic and redox properties, the synthetic variants of the planar, antiaromatic hexaphyrin (1.0.1.0.1.0) derivatives 2, has been limited due to the low yields and difficulty in access to the starting material. A chemical modification of the meso-substituents could be good alternative overcoming the synthetic barrier. Herein, we report a regio-selective nucleophilic aromatic substitution (SNAr) of meso-pentafluorophenyl group in rosarrin 2 with catechol. The reaction afforded benzodioxane fused rosarrin 3 as single product with high yield. The intrinsic antiaromatic character of the starting rosarrin 2 retained throughout the reactions. Clean, two electron reduction was achieved by treatment of 3 with SnCl2•2H2O affording 26π-electron aromatic rosarrin 4. The synthesized compounds exhibited noticeable changes in photophysical and redox properties compared with starting rosarrin 2. View Full-Text
Keywords: hexaphyrin (1.0.1.0.1.0); antiaromatic; 24π-electron system; nucleophilic aromatic substitution; aromatic; benzodioxane hexaphyrin (1.0.1.0.1.0); antiaromatic; 24π-electron system; nucleophilic aromatic substitution; aromatic; benzodioxane
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MDPI and ACS Style

Dutta, R.; Chandra, B.; Hong, S.-J.; Park, Y.; Jung, Y.M.; Lee, C.-H. Post Synthetic Modification of Planar Antiaromatic Hexaphyrin (1.0.1.0.1.0) by Regio-Selective, Sequential SNAr. Molecules 2021, 26, 1025. https://doi.org/10.3390/molecules26041025

AMA Style

Dutta R, Chandra B, Hong S-J, Park Y, Jung YM, Lee C-H. Post Synthetic Modification of Planar Antiaromatic Hexaphyrin (1.0.1.0.1.0) by Regio-Selective, Sequential SNAr. Molecules. 2021; 26(4):1025. https://doi.org/10.3390/molecules26041025

Chicago/Turabian Style

Dutta, Ranjan, Brijesh Chandra, Seong-Jin Hong, Yeonju Park, Young Mee Jung, and Chang-Hee Lee. 2021. "Post Synthetic Modification of Planar Antiaromatic Hexaphyrin (1.0.1.0.1.0) by Regio-Selective, Sequential SNAr" Molecules 26, no. 4: 1025. https://doi.org/10.3390/molecules26041025

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