Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 21, Pages 9641-9651Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301701a
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- National Science Foundation [CHE 0848206]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0848206] Funding Source: National Science Foundation
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Donor-a-Acceptor (D-sigma-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, C-19) alkane connected at midchain, on the other. Such an alkyl tail facilitates the formation of Langmuir-Blodgett (LB) monolayers. We have employed several modified swallowtails to make new D-sigma-A molecules: poly(ethylene glycol) (PEG) swallowtails with 6 ether oxygens or with 4 ether oxygens to promote hydrophilicity in orienting LB monolayers, and alkyl swallowtails ending with sulfur anchors (thioacetate, thiol, or methyl disulfide) to stabilize attachment of the D-sigma-A molecules to gold electrodes. The preparation and characterization of D-sigma-A molecules containing combinations of these swallowtails with pyrene, ferrocene, and tetramethylphenylenediamine donor groups is described.
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