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

Abstract

The symmetrical meso-tetrasubstituted porphyrin 5,10,15,20-tetrakis(4bromophenyl)Porphyrin (1) has been synthesized in quite high yields, ranging from 55 to 78%, by conventional and microwave assisted techniques, and isolated as a microcrystalline compound. The products obtained in each case have been characterized by 1 H-NMR, Mass spectrometry, elemental analysis and Thin layer chromatography. The Xray 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 mesopositions 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.

Impact of Electron-Withdrawing Effect on Sigma Hole Via Bromine-Based Interactions in Zn-5,10,15,20-tetra(4-bromo-2,6-difluoro Phenyl) Porphyrin

“…Novoa et al. reported the crystal structure of 5,10,15,20-tetrakis­(4-bromophenyl)­porphyrin in which the solid-state arrangement is dominated by C–H···N and C–H···Br interactions along with few π···π contacts . The peripheral bromine atoms on the phenyl rings located at the meso positions did not participate in any directional interactions via Br···Br or Br···π contacts.…”

Nanomaterials Based on 2,7,12,17-Tetra-tert-butyl-5,10,15,20-tetraaza-21H,23H-porphine Exhibiting Bifunctional Sensitivity for Monitoring Chloramphenicol and Co2+

“…The strong shielding effect of interna NH is moving the signal to −2.69 ppm and the strong de-shielding effect of the β-pyrroli protons, produces a doublet signal between 8.72 and 8.68 ppm, respectively. Thi shielding/de-shielding phenomenon is caused by the induced ring current as a result o the induced magnetic field [32,54], also known in the literature as an effect of diamagneti anisotropy [55], manifested when paramagnetic states with nonzero spin multiplicit have magnetic-field-dependent state energies [56]. The strongest signal appearing at 1.99 ppm is attributed to the 36 protons from th tert-butyl peripheral groups (-CH3).…”

Synthesis, Crystallographic Structure, Hirshfeld Surface Analysis, Drug-likeness Properties and Molecular Docking Studies of New Oxime-pyridine Compounds

“…According to fingerplots studies results of for HL 2 ; Cl···H 11,4%, H···H 28,7%, N···C 6,4%, N···H 6,5%, O···H 18,3%, Cl···N 2,5%, C···C 3,8%, C···H 15,2%. [22][23][24] Other bondings constituted all interactions by making small contributions on the surface. The highest H···H interaction rate (28.7%) was shown to be derived from the abundance of the H···H interactions in aromatic rings (Fig.…”