The First Spiroconjugated TTF- and TCNQ-Type Molecules:  A New Class of Electroactive Systems?

Spiroconjugated TTF-type electron donors (<b>13a</b><b>−</b><b>c</b>) and TCNQ-type electron acceptors (<b>10</b>, <b>11</b>) have been prepared from spiroquinone <b>9</b>. Cyclic voltammetry reveals a relatively weak accepting ability for <b>10</b> and <b>11</b>, and a strong electron-donor character for <b>13a</b><b>−</b><b>c</b>. Whereas the spiroconjugation introduces a destabilization of the LUMO for compounds <b>9</b>−<b>11</b>, the opposite is observed for compound <b>13</b>, thus justifying the redox potential values.