The development of organic materials that may be used in the development of sensors, semiconductors and OLEDs are often based on alkynyl-arene motifs. One such class of compounds is the o-dehydrobenzoannulenes (DBAs). o-DBAs, which have been known for many years, are cyclic structures composed exclusively of arenes bridged at the otho-position by unsaturated linkers. These compounds have become attractive targets in recent years in large part due to the synthetic accessibility of such molecules via highly reliable palladium coupling methodologies. Although early examples were primarily hydrocarbons, an ever increasing number of o-DBAs posessing heterocycles is being reported.This presentation will focus on the synthesis and characterization of a novel series of pyridine bearing o-DBAs (1  -4 ). The syntheses are highly convergent in nature, requiring only a handful of building blocks to prepare all four targets. The synthetic strategies used to prepare these compounds and their spectroscopic properties will be detailed, as well as why these targets are ideally suited for research at a PUI.

Synthetic and spectroscopic studies of a series of isomeric push-pull [14]annulenes

246th National Meeting (2013)

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