Synthesis of Oligo(phenylene ethynylene)s with Dendrimer “Shells” for Molecular Electronics

Abstract

Two series of oligo(phenylene ethynylene)s (OPEs) with different dendrimer side groups have been designed and synthesized. The molecules contain thiol groups at both ends to enable interconnection between nanoscale gapped metallic electrodes. The different dendrimer groups act as "shells", allowing tailoring to the nanoscopic environment surrounding the OPE "core". Meanwhile, the dendrimer shells also act as spacers for the precise control of the packing density and intermolecular interaction between the OPE cores. [structure: see text].

Ferrocene‐Alkynyl Conjugated Molecular Wires: Synthesis, Characterization, and Conductance Properties

“…The remaining peaks in Figure b and c belong to the molecular junctions, and the average conductance values for wires a1 – a2 are 1.67×10 −5 G 0 and 4.78×10 −6 G 0 , respectively. Three conclusions can be drawn from our experiments with wires a1 – a2 : (i) a1 has a remarkable conductivity compared with a2 because of the relatively stronger electrical coupling between the thiol group and gold electrodes; (ii) these values appear to be independent of the immersing time up to 24 h, which supports the acquired electronic data results from just one single molecule rather than a less defined aggregate, that is, the three‐dimensional structure of the ferrocene unit can really reduce the intermolecular π–π stacking during the conductance measurements; and (iii) relative to 1,1′‐substituted ferrocene wires, the alkanethiol is not necessary to be added to the coating solution co‐adsorbed with wires a1 – a2 . These observations demonstrate that the configuration for 1,2,3‐functionalized species appears to hamper the rotation of the cyclopentadienyl rings around the iron, thus preventing the wires a1 – a2 from binding onto the surface with both anchoring groups, which is beneficial to single‐molecule contacts.…”

Molecular Self‐Assembled Monolayers and Multilayers for Organic and Unconventional Inorganic Thin‐Film Transistor Applications

“…[92,95,96] Examples of thiol (R-SH) and dithiol (HS-R-SH) molecular structures ( Fig. 2A) typically deposited on Au for electronic applications are alkane(di) thiols, [97][98][99] and those based on oligophenylenes (OPs), [100][101][102][103] oligo(phenyleneethynylenes) (OPEs), and oligo(phenylenevinylenes) (OPVs), [104][105][106][107][108][109] where the labile thioacetyl (R-SAc) or disulfide (R-S-S-R) functional groups are sometimes used for substrate chemisorption instead of the R-SH group. Thiol-derived SAMs with interesting functionalities (Fig.…”

Perfluorophenyl‐Terpyridine Ruthenium Complex as Monomer for Fast, Efficient, and Mild Metallopolymerizations

“…Except for the synthesis of 1 , all solvents or solutions were degassed by bubbling with argon 1 h prior to use. Compounds 4 and 6 were synthesized according to literature procedures 13, 14. The experimental details are given in the Supporting Information.…”