The Dipole Mediated Surface Chemistry of p-Benzoquinonemonoimine Zwitterions

This article reviews the surface adsorption of p-benzoquinonemonoimine zwitterions from the class of N-alkyldiaminoresorcinones (or 4,6-bis-dialkylaminobenzene-1,3-diones, i.e. C6H2(center dot center dot center dot NHR)(2)(center dot center dot center dot O)(2)), where R = H, R = C2H5, n-C4H9), on a variety of conducting surfaces. These small molecules with a large electrical dipole exhibit molecular orientation and packing on surfaces depending on the deposition methodology (from solution or from the vapor) as well as the substrate. What is very clear from the investigations of this class of molecules is that inter-molecular interaction is not simply driven by dipolar interactions alone, but frontier orbital symmetry as well. This is illustrated by the reversible adsorption of di-iodobenzene on molecular films of (6Z)-4-(butylamino)-6-(butyliminio)-3-oxocyclohexa-1,4-dien-1-olate C6H2(center dot center dot center dot NHR)(2)(center dot center dot center dot O)(2) where R = n-C4H9, where it is clear that absorption is isomer specific.