Synthesis, characterization and crystal structures of novel fluorinated di(thiazolyl)benzene derivatives

Maciej Barłóg, Ihor Kulai, Xiaozhou Ji, Nattamai Bhuvanesh, Somnath Dey, Eric Pierre Sliwinski, Hassan S. Bazzi, Lei Fang, Mohammed Al-Hashimi

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Abstract

A series of 11 novel fluorinated and non-fluorinated di(thiazolyl)benzenes have been synthesized via microwave assisted Stille coupling and characterized using X-ray crystallography. A comparative analysis of nonbonding interactions in bis-heteroaryl-phenylene derivatives depending on the heterocycle structure and degree of fluorination of the central aromatic unit has been reported. We have systematically studied the effect of fluorination on the intramolecular interactions, π-π stacking, CH⋯F and S⋯F non-covalent interactions. Axial conformations of the biaryl system A is regulated by thermodynamic fluctuations and steric repulsions. On the other hand 2-phenyl thiophene B consists of only one H,H-repulsion interaction with a possibility of having a weak noncovalent CH⋯S interaction, hence, the combination of these factors results in the decrease in the energetics of the eclipsed conformation. When replacing the thiophene moiety with the thiazol-2-yl substituent C this allow us to eliminate the H,H-repulsions and results in CH⋯N hydrogen bonding and CH⋯S interactions. S⋯F non-covalent interactions can be used for pre-orientation of organic conjugated materials in a quasi-planar conformation.

Original languageEnglish
Pages (from-to)780-790
Number of pages11
JournalOrganic Chemistry Frontiers
Volume6
Issue number6
DOIs
Publication statusPublished - 21 Mar 2019

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ASJC Scopus subject areas

  • Organic Chemistry

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