Synthesis of donor-σ-perylenebisimide-acceptor molecules having PEG swallowtails and sulfur anchors.

Donor-σ-Acceptor (D-σ-A) molecules, arrayed in a monolayer between electrodes, can serve as molecular rectifiers. Using perylene-3,4,9,10-tetracarboxylic bisimide (PBI) as the acceptor allows the attachment of the donor group to one imide nitrogen and a solubilizing swallowtail, normally a long (e.g.

Synthesis of a non-cationic, water-soluble perylenetetracarboxylic diimide and its interactions with G-quadruplex-forming DNA.

A number of N,N'-disubstituted perylenetetracarboxylic diimides have been reported to bind effectively to DNA that adopts G-quadruplex motifs. In some cases, this binding may actively drive the transition from single-strand DNA to the quadruplex form. The perylenediimides in the reported cases all have amine-containing side chains, which are thought to interact with the grooves of the quadruplex and help dictate the selectivity of these compounds for quadruplex versus duplex DNA.

Donor-sigma-acceptor molecules incorporating a nonadecyl-swallowtailed perylenediimide acceptor.

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.