6533b7d3fe1ef96bd1261575
RESEARCH PRODUCT
Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
Reinhard BergerMichael WuttkeAlexander RissJacob DuckeAkimitsu NaritaAkimitsu NaritaAlejandro Pérez PazAlejandro Pérez PazAlejandro Pérez PazJohannes V. BarthKnud SeufertManuela GarnicaManuela GarnicaXinliang FengXiao-ye WangXiao-ye WangCarlos-andres PalmaCarlos-andres PalmaYuanqin HeRajesh RajuAngel RubioAngel RubioAngel RubioWilli AuwärterKlaus MüllenKlaus MüllenEduardo CorralMarcus Richtersubject
Materials scienceFabricationScienceGeneral Physics and Astronomy02 engineering and technologyConjugated system010402 general chemistry01 natural sciencesArticleGeneral Biochemistry Genetics and Molecular Biologylaw.inventionchemistry.chemical_compoundScanning probe microscopylawDehydrogenationon-surface synthesislcsh:Science13-dipolar cycloadditionschemistry.chemical_classificationMultidisciplinaryalgorithmGrapheneQgrapheneazomethine ylidesGeneral ChemistryPolymer021001 nanoscience & nanotechnologyCycloadditionddc:0104 chemical sciencesCU(111)total-energy calculationschemistryChemical engineeringboron-nitrideBoron nitrideazide-alkyne cycloadditionlcsh:QMaterials chemistrydehalogenation0210 nano-technologydescription
The vast potential of organic materials for electronic, optoelectronic and spintronic devices entails substantial interest in the fabrication of π-conjugated systems with tailored functionality directly at insulating interfaces. On-surface fabrication of such materials on non-metal surfaces remains to be demonstrated with high yield and selectivity. Here we present the synthesis of polyaromatic chains on metallic substrates, insulating layers, and in the solid state. Scanning probe microscopy shows the formation of azaullazine repeating units on Au(111), Ag(111), and h-BN/Cu(111), stemming from intermolecular homo-coupling via cycloaddition reactions of CN-substituted polycyclic aromatic azomethine ylide (PAMY) intermediates followed by subsequent dehydrogenation. Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry demonstrates that the reaction also takes place in the solid state in the absence of any catalyst. Such intermolecular cycloaddition reactions are promising methods for direct synthesis of regioregular polyaromatic polymers on arbitrary insulating surfaces.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-03-20 |