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

摘要

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 H-1 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 pi-pi stacking interactions, and their quantification in the crystal lattice. (C) 2019 Elsevier B.V. All rights reserved.