Phenyl–Acetylene Bond Assembly: A Powerful Tool for the Construction of Nanoscale Architectures

Jenny, Nicolas M.; Mayor, Marcel; Eaton, Thomas R.

doi:10.1002/ejoc.201100176

Cited by 65 publications

(44 citation statements)

References 115 publications

(133 reference statements)

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“…Full details of the synthesis and characterization of 4 the new OPE derivatives are given in the Supporting Information. All the OPE derivatives were characterized by 1 H NMR, 13 C NMR and mass spectra which unambiguously confirmed their structures. Additionally, a single crystal X-ray structure was obtained for OPE-4F.…”

Section: Methods Synthesismentioning

confidence: 62%

“…They are rigid, rod-like molecules with extended π-conjugation through the backbone and their functional properties can be systematically tuned by chemical synthesis. 12,13 In particular OPE3 systems (3 refers to the number of phenyl rings in the backbone) have been widely studied in metal−single-molecule−metal 2 junctions. [14][15][16][17][18][19][20][21] For the purpose of designing future single-molecule devices, it is interesting to develop strategies for independently tuning electrical, mechanical and packing properties.…”

Section: Introductionmentioning

confidence: 99%

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Structural versus Electrical Functionalization of Oligo(phenylene ethynylene) Diamine Molecular Junctions

et al. 2014

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We explore both experimentally and theoretically the conductance and packing of molecular junctions based on oligo(phenyleneethynylene) (OPE) diamine wires, when a series of functional groups are incorporated into the wires. Using the scanning tunnelling microscopy breakjunction (STM BJ) technique, we study these compounds in two environments (air and 1,2,4-trichlorobenzene) and explore different starting molecular concentrations. We show that the electrical conductance of the molecular junctions exhibits variations among different compounds, which are significant at standard concentrations but become unimportant when working at a low enough concentration. This shows that the main effect of the functional groups is to affect the packing of the molecular wires, rather than to modify their electrical properties. Our theoretical calculations consistently predict no significant changes in the conductance of the wires due to the electronic structure of the functional groups, although their ability to hinder ring rotations within the OPE backbone can lead to higher conductances at higher packing densities.

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Section: Methods Synthesismentioning

confidence: 62%

Section: Introductionmentioning

confidence: 99%

Structural versus Electrical Functionalization of Oligo(phenylene ethynylene) Diamine Molecular Junctions

et al. 2014

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“…[13,14,15] These features make them attractive molecular bridges in D-B-A molecules. An OPE bridge (comprising three phenyl units) was shown to mediate efficient electron transfer between a donor zinc phthalocyanine and acceptors pyrrolidinoC 60 or gold porphyrin with strong electronic coupling over a distance of >30 Å.…”

Section: Extensive Studies Have Focused On Covalently-linked Donor-brmentioning

confidence: 99%

Oligo(p‐phenyleneethynylene) (OPE) Molecular Wires: Synthesis and Length Dependence of Photoinduced Charge Transfer in OPEs with Triarylamine and Diaryloxadiazole End Groups

Linton

Fox

Pålsson

2015

Chemistry A European J

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Citation for published item: vintonD uFiF nd poxD wFeF nd ¦ lssonD vFyF nd fryeD wFF @PHISA 9yligo@pEphenyleneethynyleneA @yiA moleulr wires X synthesis nd length dependene of photoindued hrge trnsfer in yis with trirylmine nd diryloxdizole end groupsF9D ghemistry X iuropen journlFD PI @IHAF ppF QWWUERHHUF Further information on publisher's website: httpXGGdxFdoiForgGIHFIHHPGhemFPHIRHTHVH Publisher's copyright statement: his is the peer reviewed version of the following rtileX vintonD uF iFD poxD wF eFD ¦ lssonD vFEyF nd fryeD wF F @PHISAD yligo@pEphenyleneethynyleneA @yiA woleulr iresX ynthesis nd vength hependene of hotoindued ghrge rnsfer in yis with rirylmine nd hiryloxdizole ind qroupsF ghemistry E e iuropen tournlD PI @IHAX QWWUERHHUD whih hs een pulished in (nl form t httpXGGdxFdoiForgGIHFIHHPGhemFPHIRHTHVHF his rtile my e used for nonEommeril purposes in ordne ith ileyEgr erms nd gonditions for selfErhivingF Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. Introduction.

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“…53 While the syntheses of the two three-armed stars 3BPEB-H and 3BPEB-OH were already reported elsewhere, 47 the assembly of the four-rayed star 4BPEB-2OH is sketched in Scheme 1. As central unit a fourfold 1,2,3,5-ethynyl-substituted benzene was required, which was obtained from the commercially available 2,4,6-tribromoaniline 6, which was converted to the 1,3,5-tribromo-2-iodobenzene 7 using a variation of the Sandmeyer reaction.…”

Section: Synthesismentioning

confidence: 99%

Sequential nested assembly at the liquid/solid interface

et al. 2017

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Studying the stepwise assembly of a four component hybrid structure on Au(111)/mica, the pores of a hydrogen bonded bimolecular network of 3,4,9,10-perylenetetracarboxylic diimide (PTCDI) and 1,3,5-triazine-2,4,6-triamine (melamine) were partitioned by three and four-armed molecules based on oligo([biphenyl]-4-ylethynyl)benzene, followed by the templated adsorption of either C60 fullerene or adamantane thiol molecules. The characterisation by ambient scanning tunneling microscopy (STM) reveals that the pore modifiers exhibit dynamics which pronouncedly depend on the molecular structure. The three-armed molecule 1,3,5-tris([1,1′-biphenyl]-4-ylethynyl)benzene (3BPEB) switches between two symmetry equivalent configurations on a time scale fast compared to the temporal resolution of the STM. Derivatisation of 3BPEB by hydroxyl groups substantially reduces the switching rate. For the four-armed molecule configurational changes are observed only occasionally. The observation of isolated fullerenes and small clusters of adamantane thiol molecules, which are arranged in a characteristic fashion, reveals the templating effect of the trimolecular supramolecular network. However, the fraction of compartments filled by guest molecules is significantly below one for both the thermodynamically controlled adsorption of C60 and the kinetically controlled adsorption of the thiol with the latter causing partial removal of the pore modifier. The experiments, on the one hand, demonstrate the feasibility of templating by nested assembly but, on the other hand, also pinpoint the requirement for the energy landscape to be tolerant to variations in the assembly process.

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Phenyl–Acetylene Bond Assembly: A Powerful Tool for the Construction of Nanoscale Architectures

Abstract: [a][ ‡]Dedicated to Kenkichi Sonogashira on the occasion of his 80th birthday

Cited by 65 publications

References 115 publications

Structural versus Electrical Functionalization of Oligo(phenylene ethynylene) Diamine Molecular Junctions

Structural versus Electrical Functionalization of Oligo(phenylene ethynylene) Diamine Molecular Junctions

Oligo(p‐phenyleneethynylene) (OPE) Molecular Wires: Synthesis and Length Dependence of Photoinduced Charge Transfer in OPEs with Triarylamine and Diaryloxadiazole End Groups

Sequential nested assembly at the liquid/solid interface

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