In an effort to create new, more efficient and more general synthetic methods for dithiolene-type ligands, several new variants of this ligand-type are being investigated. All are comprised of a 1,2-alkene-o-xylyldithiolate backbone and as such exhibit steric hindrance that has yet to be explored in this context. While some dithiolene ligands can be synthesized by reacting a metal sulfido compound with an alkyne or other hydrocarbon, the ligands investigated here belong to a separate group which are produced free of a metal center. An alkenedithiolate dianion is used to subject a select halogenated ethylene to nucleophilic attack, in this case producing the desired o-xylyl protected dithiolene. It is of particular interest to investigate how these new ligand-types will behave when coordinated to representative metals. Compounds of this type - including other dichalcogenolenes (dioxolenes and diselenolenes) - are of interest namely due to their redox non-innocent behavior. This redox behavior is the crux of many potential applications, including use as conducting materials, sensing devices, and catalysts for the generation of hydrogen gas. The first new compound of the series to be prepared was (Z)-1,6-dihydrobenzo[f][1,4]dithiocine, which was characterized by 1H and 13C NMR, elemental analysis, and identified via X-Ray structure determination.

Synthesis of new dithiolene-type ligands

249th National Meeting (2015)

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