Synthesis and Properties of Aza‐ullazines

Boldt, Sebastian; Parpart, Silvio; Villinger, Alexander; Ehlers, Peter; Langer, Peter

doi:10.1002/ange.201701347

Cited by 13 publications

(5 citation statements)

References 57 publications

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“…In general, the synthesis of N‐doped PAHs differ strongly from the synthesis of their respective PAH analogues [4] . In recent years, we and others investigated the combination of Suzuki–Miyaura and Sonogashira cross‐coupling reactions with acid mediated cycloisomerizations for the synthesis of heterocyclic systems, including N‐doped PAHs [27–39] . The Povarov reaction represents an [4+2] aza‐Diels–Alder cycloaddition with inverse electron demand which results in formation of quinolines [40–41] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Diphenylbenzo[j]naphtho[2,1,8‐def][2,7]phenanthrolines

Mertz

Molenda

Boldt

et al. 2023

Chemistry A European J

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A series of hitherto unknown 5,14‐diphenylbenzo[j]naphtho[2,1,8‐def][2,7]phenanthrolines, containing a 5‐azatetracene and a 2‐azapyrene subunit, were prepared by combination of Pd‐catalyzed cross‐coupling reactions with a one‐pot Povarov/cycloisomerization reaction. In the final key step four new bonds are formed in one step. The synthetic approach allows for a high degree of diversification of the heterocyclic core structure. The optical and electrochemical properties were studied experimentally and by DFT/TD‐DFT and NICS calculations. Due to the presence of the 2‐azapyrene subunit, the typical electronic nature and characteristics of the 5‐azatetracene moiety are lost and the compounds are electronically and optically more related to 2‐azapyrenes.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Diphenylbenzo[j]naphtho[2,1,8‐def][2,7]phenanthrolines

Mertz

Molenda

Boldt

et al. 2023

Chemistry A European J

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“…Here, we present a covalent intermolecular cycloaddition reaction of CN-functionalized PAMY with itself, into onedimensional polyaromatic chains with azaullazine 26 repeating units on metals, insulating layers, and in the solid state. Scanning tunneling microscopy (STM) and bond-resolved atomic force microscopy (AFM) with CO-functionalized tips demonstrates that on all investigated substrates, i.e., Au(111), Ag(111), and hexagonal boron nitride (h-BN) on Cu(111), phenanthridinium precursors predominantly form covalently coupled chains with repeating units of 1-azadibenzo[d,k]ullazine via the cycloaddition reaction 27,28 between the cyano group and the azomethine ylide moiety, as well as subsequent dehydrogenation (see Fig.…”

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confidence: 99%

Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions

et al. 2020

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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 nonmetal 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.

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“…In a short period of time, Sebastian managed to develop a synthesis of 6-azaullazines by combination of Pd-catalyzed cross-coupling with cycloisomerization reactions. 9 These compounds contain a pyrrole and a pyridine moiety and constituted at that time a new heterocyclic core structure. In general, nitrogen-doped polycyclic aromatic hydrocarbons (PAHs) are of considerable current interest in materials science.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Heterocycles by a C–C Cross-Coupling/Alkyne-Carbonyl-Metathesis Strategy

Langer

2024

Synlett

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The present article presents a personal account on the synthesis of heterocycles by the combination of regioselective Pd-catalyzed cross-coupling reactions of polyhalogenated heterocycles, i.e., Suzuki–Miyaura and Sonogashira reactions, with alkyne-carbonyl-metathesis (ACM) reactions. The products, which show interesting optical, electronic or medicinal properties, are not readily available by other methods.

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Synthesis and Properties of Aza‐ullazines

Cited by 13 publications

References 57 publications

Synthesis and Properties of Diphenylbenzo[j]naphtho[2,1,8‐def][2,7]phenanthrolines

Synthesis and Properties of Diphenylbenzo[j]naphtho[2,1,8‐def][2,7]phenanthrolines

Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions

Synthesis of Heterocycles by a C–C Cross-Coupling/Alkyne-Carbonyl-Metathesis Strategy

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