The Dipole Mediated Surface Chemistry of p-Benzoquinonemonoimine Zwitterions

Electrochromic Platinum(II) Complexes Derived from Azobenzene and Zwitterionic Quinonoid Ligands: Electronic and Geometric Structures

“…The zwitterionic molecule 4-(isopropylamino)-6-(isopropyliminio)-3-oxocyclohexa-1,4-dien-1-olate (Q) and other members of the series with different N substituents have been shown previously to possess many fascinating properties . Recently, properties of these and related ligands on various surfaces have been explored . Metal complexes of these ligands in their deprotonated forms have displayed unusual bonding and electronic properties. , Such complexes have found use in homogeneous catalysis, supramolecular chemistry, and electron transfer research .…”

Adsorption of TCNQH-functionalized quinonoid zwitterions on gold and graphene: evidence for dominant intermolecular interactions

“…6,7 These molecules were used as a model system for surface adsorption studies, taking advantage of their significant dipole moment of ca. 10 Debyes across a short distance, in order to gain a better insight into electrostatic contributions to surface adsorption phenomena.…”

“…5 Chemical modifications of the p-benzoquinonemonoimine zwitterions (see graphical abstract and the molecules of Fig. 1) used in adsorbate thin films can lead to supramolecular assemblies 2,6,8 (like that observed for tetracyanoquinodimethane (TCNQ)) [9][10][11][12][13][14][15][16] and possibly better hole-electron charge separation. The latter could significantly influence the exciton recombination rate, a key issue in organic solar cell optimization, and reports illustrate how the addition of dipolar molecules improves solar cell efficiencies.…”

“…A number of p-benzoquinonemonoimine zwitterion adsorbate thin films have now been investigated, using deposition from solution [1][2][3][4][5][6] or from the vapour phase. 6,7 These molecules were used as a model system for surface adsorption studies, taking advantage of their significant dipole moment of ca. 10 Debyes across a short distance, in order to gain a better insight into electrostatic contributions to surface adsorption phenomena.…”

“…1) also makes possible comparative studies of molecular thin films adsorption. 2 In general, there is pronounced adlayer ordering, with a variety of molecular orientations and packing arrangements from upright 1,2 to lying flat [5][6][7] that depend on both the method of deposition and the substrate, owing to varying adsorbate-substrate interactions. 5 Chemical modifications of the p-benzoquinonemonoimine zwitterions (see graphical abstract and the molecules of Fig.…”