Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 26, Pages 10058-10066Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo035409w
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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 H-1 and C-13 NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the C-13 NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.
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