Defined Oligo(<i>p-</i>phenylene−butadiynylene) Rods

Mössinger, Dennis; Jester, Stefan‐S.; Sigmund, Eva; Müller, Ute; Höger, Sigurd

doi:10.1021/ma901155d

Cited by 40 publications

(29 citation statements)

References 50 publications

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“…1,4-dihexyl-2,5-diiodobenzene [33] (4, 400 mg, 0.8 mmol, 1 equiv.) ), CuI (30.5 mg, 0.16 mmol, 0.2 equiv.)…”

Section: 4-bis[2-(4-bromophenyl)ethynyl]-25-dihexylbenzene (2)mentioning

confidence: 99%

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Synthesis and Solid‐State Investigations of Oligo‐Phenylene–Ethynylene Structures with Halide End‐Groups

Jenny¹,

Wang²,

Neuburger³

et al. 2012

Eur J Org Chem

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In the field of material science functionalization of substrate surfaces (e.g. metal, graphite) with organic molecules is of increasing interest. Desirable targets are molecules with functional groups providing for two‐dimensional assembly and three‐dimensional crystal growth. We have synthesized a series of halogen‐end‐capped oligo‐phenylene‐ethynylenes (OPEs) to study the interactions at the solid/liquid interface and in crystal structures. Organohalides can be involved in a wide variety of intermolecular interactions such as C–X···H, C–X···X–C and C–X···π‐orbitals. The range of halogen‐based interactions and the diversity of intermolecular forces along different crystal axes makes the investigation of such structures particular interesting and challenging. Here we probe the interplay of halide end‐groups and the backbone of an OPE to investigate the intermolecular interactions in both solution depositions (2D) and X‐ray crystal structures (3D). The STM images and the crystal structures of each OPE reveal striking packing similarities. For each molecule, a plane in the crystal structure with an arrangement of molecules resembling its two‐dimensional packing on a flat surface was found. These results support the hypothesis of sheet‐by‐sheet crystal growth and suggest that flat surfaces would be ideal interfaces to promote crystal growth for halide‐end‐capped OPEs.

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“…1,4-dihexyl-2,5-diiodobenzene [33] (4, 400 mg, 0.8 mmol, 1 equiv.) ), CuI (30.5 mg, 0.16 mmol, 0.2 equiv.)…”

Section: 4-bis[2-(4-bromophenyl)ethynyl]-25-dihexylbenzene (2)mentioning

confidence: 99%

“…Schlenk tube was purged with argon and charged with 1,4-diiodo-2,5-dihexylbenzene [33] (4, 996 mg, 2 mmol, 1 equiv. ), Pd(PPh 3 ) 2 Cl 2 (141 mg, 0.2 mmol, 0.1 equiv.…”

Section: 4-bis[2-(4-aminophenyl)ethynyl]-25-dihexylbenzene (8): a mentioning

confidence: 99%

Synthesis and Solid‐State Investigations of Oligo‐Phenylene–Ethynylene Structures with Halide End‐Groups

Jenny¹,

Wang²,

Neuburger³

et al. 2012

Eur J Org Chem

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“…Phenylen‐Butadiinylen‐Oligomere [1]n entstanden durch oxidative Glaser‐Kupplung des entsprechenden Bisacetylens 5. Diese Art der CC‐Verknüpfung ist sehr tolerant gegenüber funktionellen Gruppen und leicht durchführbar 6.…”

Section: Ergebnisse Für Lineare Oligomereunclassified

Oligomere trennen mit Recycling‐GPC

Höger

2011

Nachr Chem

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“…The chemistry required to build up the OPE wire is based on Sonogashira coupling reactions, [61] which are well known for their reliability and efficiency. [62][63] This stepwise assembly of the OPE wire allowed the length of the molecular rod to be adapted to the dimensions of the junction. Target structures 1-4 are centrosymmetric.…”

Section: Synthetic Strategymentioning

confidence: 99%

Synthesis and Optical Properties of Molecular Rods Comprising a Central Core‐Substituted Naphthalenediimide Chromophore for Carbon Nanotube Junctions

et al. 2010

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The synthesis of a series of molecular rods 1–5, designed to bridge the gap of a carbon nanotube junction in order to emit light as a characteristic signal of integrated molecules, is reported. The molecular rods consist of a central naphthalenediimide (NDI) core, which itself is substituted with benzylamino and benzylsulfanyl groups, providing distinct absorption and emission properties. The NDI core is embedded in an oligo(phenylene ethynylene) (OPE) system providing the rod‐like structure required to bridge gaps between nanoelectrodes. The number of repeating units of the OPE is varied to adjust the length of the target compounds between 2.3 and 6.6 nm. The OPE parts are terminally functionalized with polyaromatic hydrocarbon groups (naphthalene, phenanthrene, anthracene or pyrene), which possess affinity with the surface of the carbon nanotubes due to van der Waals interactions. Synthetic protocols based on Sonogashira–Hagihara couplings were developed to build up the OPE backbone. Bifunctional iodophenyl acetylene derivative 33 served as a key building block in a coupling–deprotecting–coupling sequence. The NDI building block was synthesized by an aromatic nucleophilic substitution reaction of 2,6‐dichloro‐1,4,5,8‐tetracarboxylic acid naphthalenediimide derivative 9 and the corresponding amine and sulfide (i.e., 11, 12), respectively. The convergent synthesis allows modular assembly of the NDI and OPE parts in a final Sonogashira–Hagihara coupling reaction. The target structures were fully characterized by NMR spectroscopy and mass spectrometry. Further, the optical properties of compounds 3–5 in solution, and on a graphene surface were qualitatively investigated. A Dexter‐type energy transfer from the OPE unit to the NDI unit was observed. The studies of target structures 3–5 revealed that diamino‐functionalized compound 3 is ideally suited for the envisaged single molecule electroluminescence experiments.

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Defined Oligo(p-phenylene−butadiynylene) Rods

Cited by 40 publications

References 50 publications

Synthesis and Solid‐State Investigations of Oligo‐Phenylene–Ethynylene Structures with Halide End‐Groups

Synthesis and Solid‐State Investigations of Oligo‐Phenylene–Ethynylene Structures with Halide End‐Groups

Oligomere trennen mit Recycling‐GPC

Synthesis and Optical Properties of Molecular Rods Comprising a Central Core‐Substituted Naphthalenediimide Chromophore for Carbon Nanotube Junctions

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