Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics

Berger, Reinhard; Wagner, Manfred; Feng, Xinliang; Müllen, Kläus

doi:10.1039/c4sc02793k

Cited by 76 publications

(67 citation statements)

References 36 publications

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“…Moreover, in the pyrrole core, C−N (F) bond length is 1.39 Å and the C−C (D and E) bond lengths are 1.41 and 1.43 Å, respectively (Figure b). The bond lengths of the pyrrole and pyridazine motifs are in agreement with the literature values . Crystals of PP‐2 are arranged in a brick‐wall fashion with π‐π distance of 3.40 Å between neighboring molecules (Figure c).…”

Section: Figuresupporting

confidence: 88%

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The synthesis and the analytical data of 8H-isoquinolino[4,3,2-de] phenanthridinium tetrafluoroborate (1 a) and 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridinium tetrafluoroborate (1 b) were reported in our previous work. [7][8] 2 3 4 5 6 7 8

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confidence: 99%

“…[7] Besides the dimerization of PAMYs to pyrazine-embedded PAHs at high temperatures, the zwitterionic character enables the 1,3-dipolar cycloaddition at room temperature, which serves as an efficient strategy for the synthesis of pyrrole-incorporated PAHs. [7][8] Recently, our group, as well as Ito's group, extended the range of dipolarophiles and reported on the cycloaddition of PAMYs with asymmetric or pristine carbon dipolarophiles, such as 1,2naphthoquinone and coronene, respectively. [9] Herein, we present the synthesis of unprecedented N-PAHs containing a diphenyl-substituted pyrrolopyridazine core (PP-1 and PP-2) via cycloaddition with PAMY as key step, and subsequent condensation with hydrazine.…”

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Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core

Richter

Dmitrieva

et al. 2019

ChemPlusChem

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Polycyclic aromatic azomethine ylides (PAMYs) are versatile building blocks for the bottom‐up construction of unprecedented nitrogen‐containing polycyclic aromatic hydrocarbons (N‐PAHs). Here, we demonstrate the 1,3‐dipolar cycloaddition between PAMY and 1,4‐diphenylbut‐2‐yne‐1,4‐dione and the subsequent condensation reaction with hydrazine, which led to unique N‐PAHs with a phenyl‐substituted pyrrolopyridazine core (PP‐1 and PP‐2). The molecular structures of pristine PP‐1 and tert‐butyl‐substituted PP‐2 were verified by NMR spectroscopy and mass spectrometry. Moreover, the structure of PP‐2 was unambiguously elucidated by X‐ray single crystal analysis. The optoelectronic properties were investigated by solvent‐dependent UV‐Vis absorption and fluorescence emission spectroscopy as well as cyclic voltammetry. Additionally, density functional theory (DFT) calculations showed that PP‐1 and PP‐2 exhibit push–pull behavior. Furthermore, in situ EPR/UV‐Vis‐NIR spectroelectrochemistry allowed the detailed insight into the spectroscopic properties and spin distribution of radical cation species of PP‐2.

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Section: Figuresupporting

confidence: 88%

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Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core

Richter

Dmitrieva

et al. 2019

ChemPlusChem

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“…12). 152 Nozaki et al found that 61 can also react with fullerene C 60 to form an adduct. Dibenzoazaphenalenes 61 and 62 are featured with azomethine ylide structures, showing extremely high chemical reactivity, and thus they were generated only under inert conditions.…”

Section: Heteroatom-doped Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting renewed and more widespread attention since the first experimental demonstration of graphene in 2004. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. The precise synthesis of quasi-zero-dimensional nanographenes, i.e. graphene molecules, has witnessed rapid developments over the past few years, and these developments can be summarized in four categories: (1) non-conventional methods, (2) structures incorporating seven- or eight-membered rings, (3) selective heteroatom doping, and (4) direct edge functionalization. On the other hand, one-dimensional extension of the graphene molecules leads to the formation of graphene nanoribbons (GNRs) with high aspect ratios. The synthesis of structurally well-defined GNRs has been achieved by extending nanographene synthesis to longitudinally extended polymeric systems. Access to GNRs thus becomes possible through the solution-mediated or surface-assisted cyclodehydrogenation, or "graphitization," of tailor-made polyphenylene precursors. In this review, we describe recent progress in the "bottom-up" chemical syntheses of structurally well-defined nanographenes, namely graphene molecules and GNRs.

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“…[2] In recent years, several reports on the syntheses of related structures have been published. [10] Moreover,n oble-metal (Pd, [8,11] Ru, [12] Rh [13] )c atalyzed CH-activating annulation reactions have been developed as powerful tools for the syntheses of related scaffolds. [10] Moreover,n oble-metal (Pd, [8,11] Ru, [12] Rh [13] )c atalyzed CH-activating annulation reactions have been developed as powerful tools for the syntheses of related scaffolds.…”

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Synthesis and Properties of Aza‐ullazines

et al. 2017

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Ar ange of aza-ullazines,w hichr epresent an ew heterocyclic core structure,were synthesized through ascalable four-step reaction, including aSonogashira reaction and metalfree cyclization promoted by p-toluenesulfonic acid. The optical and electrochemical properties of selected derivatives were investigated, they were found to have similar absorption and emission spectra but ahigher oxidation potential than the parent ullazine core.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: http://dx.

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Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics

Abstract: Based on polycyclic aromatic azomethine ylides, a metal-free “cycloaddition-planarization-sequence” is proposed, providing a unique entry to nitrogen-containing polycyclic aromatic hydrocarbons.

Cited by 76 publications

References 36 publications

Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core

Polycyclic Aromatic Hydrocarbons Containing A Pyrrolopyridazine Core

New advances in nanographene chemistry

Synthesis and Properties of Aza‐ullazines

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