Oligoether-Substituted Derivatives of Carbon-Rich 1,4,7,10,13,16-Hexaethynyltribenzo[a,e,i]cyclododeca-5,11,17-triyne (C₃₆H₁₂) and 1,4,9,12-Tetrakis(ethynyl)dibenzo[a,g]cyclododeca-5,7,13,15-tetrayne (C₂₈H₈): Potential Precursors to the Circular [6]Phenylene (‘Antikekulene’) Frame

Abstract

The title compounds, in which the terminal alkyne functions are adorned with -CH₂OCH₂CH₂OCH₂CH₂OCH₂CH₃ or -p-C₆H₄OCH₂CH₂ OCH₂CH₂OCH₃ substituents, were synthesized. The strategies for their preparation relied on prior art and involved the use of Sonogashira alkynylations of appropriate haloarenes, Stephens–Castro cyclizations of 1,2,4-trialkynyl-3-iodobenzenes, and Hay oxidative couplings of 1,2,3,4-tetralkynylbenzenes. The targets form yellow materials, exhibiting yellow-green fluorescence, and they are very soluble in polar solvents, but only sparingly so in nonpolar media. Attempts to convert them into the antikekulene frame through CpCo(CO)₂-catalyzed (co)-cyclizations failed.

Key words

alkynes - carbon-rich compounds - cyclotrimerizations - dehydroannulenes - phenylenes

• References


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