| Abstract
| - Donor−σ−acceptor−lipid molecules were prepared by using perylenetetracarboxylic diimide as theacceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached toa “swallowtail” lipid (a long alkyl tail connected at midchain), which imparts enough solubility tomake the system tractable and provides a lipophilic region suitable for promoting Langmuir−Blodgett monolayer formation. The other imide link was to a donor group (pyrene, ferrocene,tetramethylphenylenediamine, phenyl) through a short alkyl σ bridge. Features of the 1H and 13CNMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotationabout the imide C−N bond; the 13C NMR spectra and stereochemistry of these molecules arecontrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.
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