Efficient preparation of 5,10,15,20-tetrakis(4-bromophenyl)porphyrin. Microwave assisted v/s conventional synthetic method, X-ray and hirshfeld surface structural analysis

Edison Matamala-Cea (1) , Fabian Valenzuela-Godoy (1) , Déborah González (1) , Rodrigo Arancibia (1) , Vincent Dorcet (2) , Jean-René Hamon (2) , Nestor Novoa (1)

1 Universidad de Concepción - University of Concepcion [Chile]
2 ISCR - Institut des Sciences Chimiques de Rennes

The symmetrical meso-tetrasubstituted porphyrin 5,10,15,20-tetrakis(4-bromophenyl)Porphyrin (1) has been synthesized in quite high yields, ranging from 55 – 78%, by conventional and microwave assisted techniques, and isolated as a microcrystalline compound. The products obtained in each case have been characterized by 1H NMR, Mass spectrometry, elemental analysis and Thin layer chromatography. The X-ray crystal structure of 1 is reported for the first time, and reveals a planar disposition of the center of the macrocycles with almost orthogonal 4-bromophenyl rings in the four meso-positions in the solid state. Hirshfeld surface (HS) analysis along with 2D fingerprint plots were employed to consider the intermolecular forces, including hydrogen bonds and π–π stacking interactions, and their quantification in the crystal lattice.

Keywords: Hirshfeld surface analysis; Meso-tetraporphyrins; Microwave assisted synthesis; Single crystal X-ray diffraction

Domains: Chemical Sciences

Edison Matamala-Cea, Fabian Valenzuela-Godoy, Déborah González, Rodrigo Arancibia, Vincent Dorcet, et al.. Efficient preparation of 5,10,15,20-tetrakis(4-bromophenyl)porphyrin. Microwave assisted v/s conventional synthetic method, X-ray and hirshfeld surface structural analysis. Journal of Molecular Structure, 2020, 1201, pp.127139. ⟨10.1016/j.molstruc.2019.127139⟩. ⟨hal-02367901⟩