Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Post Synthetic Modification of Planar Antiaromatic Hexaphyrin(1.0.1.0.1.0) By Regio-selective, Sequential SNAr

Version 1 : Received: 18 January 2021 / Approved: 19 January 2021 / Online: 19 January 2021 (13:30:55 CET)

A peer-reviewed article of this Preprint also exists.

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. 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.

Journal reference: Molecules 2021, 26, 1025
DOI: 10.3390/molecules26041025

Abstract

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 26pi-electron aromatic rosarrin 4. The synthesized compounds exhibited noticeable changes in photophysical and redox properties compared with starting rosarrin 2. .

Subject Areas

Hexaphyrin(1.0.1.0.1.0); Antiaromatic; 24π-electron system; Nucleophilic Aromatic substitution; Aromatic; Benzodioxane

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