Synthesis and Evaluation of Perylenebisimide-Derived Donor-Sigma-Acceptor Molecules as Electrical Rectifiers

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The Aviram-Ratner model of orbital energy levels predicts that monolayer arrays of Donor Sigma-Acceptor (D-?-A) molecules will pass electrons in only one direction, that is, D-?-A molecules should be able to rectify electricity. In this project a new class of materilas incorporating perylenebis(dicarboximide) as a new D-?-A acceptor, and/or a related tetralkylperylene as a new D-?-A donor, will be prepared and evaluated as potential rectifiers of electrical current. The molecular orbital levels of these groups are well situated for the D-?-A task. The perylene-based donors and acceptors have two synthetic handles, allowing the convenient attachment of the -?- bridge between them, as well as "tails" to the other ends. These tails are required both to improve solubility and to permit the formation of the monolayers required to evaluate rectification. Monolayer films will be controlled to form in either the D-?-A or A-?-D orientation by the appropriate selection of tails. The relatively polar polyethyleneglycol (PEG) tails proposed for some targets should improve current flow compared to nonpolar alkyl tails. Whereas rectification has been reported recently from D-?-A multilayers as well as from D-?-A monolayers, the Aviram-Ratner model properly applies to D-?-A monolayers. The proposed research will test these systems. . The D-?-A targets will be synthesized at the University of Mississippi, and will be evaluated for film-formation and electrical properties at the University of Alabama.%%%The investigation of molecular-scale rectification is of far-reaching practical interest because it could lead to greatly miniaturized electronic devices. This is an important goal in the world of nanoelectronics. This project provides a significant opportunity for substantial advancements in the training of young minority scientists from Mississippi and Alabama.