title: Donor-sigma-acceptor molecules incorporating a nonadecyl-swallowtailed perylenediimide acceptor.
abstract: Donor-sigma-acceptor-lipid molecules were prepared by using perylenetetracarboxylic diimide as the acceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached to a "swallowtail" lipid (a long alkyl tail connected at midchain), which imparts enough solubility to make 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 sigma bridge. Features of the 1H and 13C NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the 13C NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.
authors.affiliation: Department of Chemistry and Biochemistry, University of Mississippi, Box 1848, University, Mississippi 38677, USA.
authors.forename: Lyle D
authors.initials: LD
authors.lastname: Wescott
authors.forename: Daniell Lewis
authors.initials: DL
authors.lastname: Mattern