By James, Dustin K., Tour, James M.
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12, Gourdon and coworkers have synthesized two classes of conjugated ladder oligomers [59] that maintain similar guidelines for molecular wires, including a defined length, rigidity, extended π-conjugation for good electron transfer, and good electronic coupling with metallic con- Fig. 12 Gourdon [59] synthesized the aromatic ladder oligomers oligo(quinoxaline) 51 and the oligo(benzoanthracene)s 52 Molecular Wires 47 Fig. 13 Ladder polyaromatics 53–55 synthesized by our group to study proposed molecular electronic switching mechanisms [61] tacts.
Note that 45 is unfunctionalized, containing only a protected thiol alligator clip for later SAM formation. K. M. Tour Fig. 9 Three oligo(phenylene vinylene)s (OPVs) 45–47 synthesized in order to compare their conductance to OPEs [48] ring. We functionalized 46 with a nitro group on the interior aromatic core in order to determine if 46 would then act as a switch. Compound 46 is undergoing testing in a collaborator’s lab. Finally, 47 was synthesized with both a nitro functional group and protected thiol groups at both ends so that it could span two Au contacts and form a circuit via a self-assembly process.
Surface analysis by ellipsometry, contact angle goniometry, CV, surface infrared and XPS verified that the fluorinated OPEs chemisorb on Au and Pt surfaces. Based on the physical properties of the fluorinated OPEs, they might be useful in future physical vapor deposition techniques, methods that are typically used in standard semiconductor fabrication processes. We have also synthesized orthogonally functionalized OPEs 40–44, see Fig. 8 [45]. We have designed these compounds to allow for self-assembly of the molecules via the free thiol or nitrile while protecting the other sulfur atom as a thioacetate to ensure molecular directionality and to inhibit crosslinking if SAM assembly on nanorods is desired.