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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 ( IF 4.0 ) Pub Date : 2020-02-01 , DOI: 10.1016/j.molstruc.2019.127139
Edison Matamala-Cea , Fabián Valenzuela-Godoy , Déborah González , Rodrigo Arancibia , Vincent Dorcet , Jean-René Hamon , Néstor Novoa

Abstract 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.

中文翻译:

5,10,15,20-四(4-溴苯基)卟啉的高效制备。微波辅助v/s常规合成方法,X射线和Hirshfeld表面结构分析

摘要 对称的内消旋四取代卟啉 5,10,15,20-四(4-溴苯基)卟啉 (1) 已通过常规和微波辅助技术以相当高的产率合成,产率为 55-78%,并分离为一种微晶化合物。在每种情况下获得的产物已经通过1H NMR、质谱、元素分析和薄层色谱表征。首次报道了 1 的 X 射线晶体结构,并揭示了大环中心的平面布置,在固态的四个介位中具有几乎正交的 4-溴苯环。Hirshfeld 表面 (HS) 分析和 2D 指纹图被用来考虑分子间力,包括氢键和 π-π 堆积相互作用,以及它们在晶格中的量化。
更新日期:2020-02-01
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