Cyclotri(<i>m,p,m,o</i>)tetraphenylene macrocycles, which are precursors and models of carbon single-walled nanobelts, can be obtained by performing a Diels-Alder cycloaddition on each alkyne moiety in a cyclo(phenylene ethynylene) macrocycle. Computational modeling at the molecular mechanics, semi-empirical, and ab initio levels of theory predict the symmetrical triadduct to be preferred over the asymmetrical triadduct. The phenylene ethynylene macrocycles have been prepared using high dilution Sonogashira cross-coupling of ethynylaryl iodides. Diels-Alder cycloadditions of these macrocycles using both high temperature reactions with tetraphenylcyclopentadienone and lower temperature, copper(I) catalyzed benzannulations with phenylethynylbenzaldehyde are described. These cycloaddition products have been characterized with MALDI mass spectroscopy.

Cyclooligo-(para, ortho)-phenylenes obtained by threefold Diels-Alder benzannulation of phenylene ethynylene macrocycles: Examination of the toposelectivity of cycloadditions to macrocycles by experiment and theory

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.