Several donor−σ−acceptor compounds (8, 9, 13, and 14) have been synthesized that contain a sterically hindered quinone tethered by a tetramethylene chain to a substituted tetrathiafulvalene. Compounds 13 and 14 show a dramatic increase (≈450 mV) in the oxidation potential of the dipyrrolo-TTF unit, suggestive of considerable electron withdrawal through the σ-bridge. Monolayers of 9 and 14 are metastable at the air−water interface.
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Scheib et al. (1998) studied this question.
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