(1E,3E,5E)-1,2,3,4,5,6-Hexafluoro-1,6-diphenylhexatriene

Area of Science:

• Organic Chemistry
• Materials Science

Background:

• Fluorinated organic compounds exhibit unique electronic and steric properties.
• Trienes are versatile building blocks in organic synthesis.
• Palladium-catalyzed cross-coupling reactions are crucial for C-C bond formation.

Purpose of the Study:

• To synthesize a novel fluorinated triene (C18H10F6).
• To determine the stereochemistry and solid-state structure of the synthesized triene.
• To investigate the impact of fluorine substituents on the triene's geometry.

Main Methods:

• Synthesis via Pd(0) coupling reaction.
• Utilized (E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane) and (Z)-beta-iodo-alpha,beta-difluorostyrene.
• Characterization using X-ray crystallography.

Main Results:

• Successfully synthesized the title triene, C18H10F6.
• The crystal structure confirmed the 1E,3E,5E isomer.
• Steric interactions of fluorine atoms caused non-planar double bonds, with terminal double bond planes nearly perpendicular.

Conclusions:

• The Pd(0) coupling is effective for synthesizing complex fluorinated trienes.
• Fluorine substitution significantly influences molecular geometry and conformation.
• The study provides insights into the structure-property relationships of fluorinated organic molecules.