Bis-indenylidene dications are formally antiaromatic species consisting of two antiaromatic indenyl cations joined by a single bond. Their antiaromaticity can be evaluated by various theoretical measures such as the nucleus independent chemical shift (NICS), which suggest that the electronic nature of substitutents and their placement can dramatically alter the magnitude of their antiaromaticity. We will describe our approach to the preparation of precursors to a variety of substituted bis-indenylidene dications such as the ones shown below.

Effect of substituents on the antiaromaticity of bis-indenylidene dications

245th National Meeting (2013)

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