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 progress in the synthesis and characterization of a novel series of pyridine bearing o-DBAs (1 - 4 ). These compounds are designed to investigate how the relative orientations of electron-donating and withdrawing atoms on the annulene affect each molecule's spectroscopic proterites. In addition, the interactions 1 - 4 with metal cations may result in spectral changes that could find utility in area of metal detection. All four targets can be prepared from a few common starting materials, and the synthetic strategies used to prepare these compounds will be detailed. The NMR and UV-Vis spectroscopic characteristics of these compounds and their acyclic precursors will also be compared with each other, as well as with previously prepared isomeric compounds. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/239nm/uploads/15982_fig.1_copy.w3k_gel_sem.jpg' alt='' />

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

246th National Meeting (2013)

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